What Is The Freedom Trail?

The Freedom Trail is Boston’s way of linking some of its most important historic sites together in an easy to follow trail through its downtown area. And by easy to follow, I mean exactly that. The trail is a line of inlaid bricks set into the sidewalk or painted onto the paved streets. It even continues over bridges. You don’t even need a map to follow it— it is that user friendly. The kids loved leading the way, treating it like a really long scavenger hunt.

* Pro Tip- You may not need a map but download the PDF brochure from the official website to help you recognize the 16 historic sites along the trail when you come across them. There are so many historic buildings in Boston, it is not always immediately clear which are the ones you should be looking for.

The Freedom Trail is 2.5 miles long, includes 16 historic sites, and extends from Boston Common to Bunker Hill.

I always try to walk at least part of the Freedom Trail anytime I visit Boston, because it is a great way to explore the highlights of the city while getting a refresher course on some of the most important events and people from our colonial and revolutionary days.

I was a little worried about walking the trail during winter and thought the kids might complain about being cold. It turns out, however, I like it better than doing it during the summer. The sites are close enough together that you can walk a little, then pop into a building to tour it and warm up a bit. And the lack of fellow tourists meant I saw some of the places more thoroughly and learned more than I ever have on previous visits. Only in a few places, Boston Common being one (because it is a park and it was really windy the day we saw it), did we spend less time than we would have at other times of year.

Speaking Of The Weather, What Was It Like In January?

It was not nearly as cold as I was expecting. This is not to say it was warm, it just wasn’t the frigid conditions I was anticipating. Boston’s proximity to the ocean keeps it more moderate than its latitude might suggest.

We were lucky and had above average temperatures most of the days we were there with a high around 50 and a low around 40 (historic averages are 36-40 and 23- 28). It did drizzle rain one day, but it is actually no more likely to rain in winter than other times of the year (8 days on average per month). It also generally gets less than an inch of snow in January or February.

The wind can be a game changer (as any coastal person knows first hand) and Boston is more likely to have higher average wind speeds in winter than summer (9 mph versus 5 mph) so watch out for that.

As a tourist, the only real drawback was the limited daylight. Because Boston is so far east, the sun rises early (around 7 am) and sets early (before 5 pm) giving you a little more than 9 hours of daylight. This is not helpful when most of the tourist sites don’t open until 10 am. It means you are either squeezing all the sights into a shorter amount of time, or you are happy seeing some attractions in the dark. Which is actually okay. The Bunker Hill Monument is beautifully lit at night for instance.

*February is a bit better than January with 10-11 hours of daylight and a sunset after 5 pm.

Packing List For Boston Winter Weather

• Warm jackets that are also waterproof (good for rain and wind). Or a puffy jacket/ vest and shell— this is a good combo that covers a lot of potential weather scenarios.

• Toboggans, gloves, and scarves. The scarf is your best friend when it’s windy.

Northerners may think this list sounds obvious but us southerners usually don’t wear all that unless we are skiing. I had to convince my preteen niece, unused to a scarf, that it is fashionable in other places. She refused to pack one, then stole mine the whole time we were there once she realized how useful they are. Isn’t that how that usually turns out?

How Long Does It Take To Walk The Freedom Trail?

It will take about 2 hours to walk the entire trail straight if you don’t go inside any of the sites and just read the informational plaques along the way. But I recommend that you plan on doing the trail over at least 2 days so you have time to go inside most of the sites and explore. Take advantage of the opportunity that winter gives you to see these places without hordes of fellow tourists.

Plus, most kids will have a history overload after about 5- 6 sites on the trail so best to do it over more than one day unless you have an immunity to whining (and if you do, please share how you accomplish that). If you only have one day, plan on doing whatever part of the trail interests you most and leave the other parts for your next visit. I promise you, everyone will enjoy it more.

We split the trail over 3 days and really took our time:

• Copp’s Hill Burying Ground to Faneuil Hall on day 1 (0.8 miles)

• Bunker Hill and the USS Constitution on day 2 (0.5 miles between the 2 sites). Bunker Hill and the USS Constitution are good to do together as they are both in Charlestown, a neighborhood just across the Charles River from downtown Boston, easily accessible across a bridge with a wide sidewalk

• Boston Massacre Site to Boston Common on day 3 (0.7 miles).

*My mileage doesn’t add up to 2.5 miles because I am leaving out some of the Freedom Trail between the sites since we kept leaving and coming back to the trail on different days.

A Word About Getting Around The Freedom Trail

We walked everywhere because we stayed in a very central location. Boston is a very walkable city with decent sidewalks, occasional pedestrian streets, and signaled crosswalks. (Don’t jaywalk though, Boston drivers will take you out.)

You can also use the T (Boston’s subway) to get around. It is a system with pretty wide coverage downtown and is easy to use, even if it is looking a little worn. I write more detail about Boston transportation at the end of this blog.

The Complete Rundown Of All The Sites We Saw

(The numbering is my own so I could keep track but you can do the trail in any order that works for you, it really doesn’t matter. We did #3- #6 on day 1 and #1 & #2 on day 2 because of weather.)

1. Bunker Hill Monument

Thanks to the 430 pm sunset while we were visiting, we saw the Bunker Hill Monument at night and were not able to climb up to the top of the monument. But it was still a worthwhile stop because it is beautifully lit at night and has a great view of lights of downtown Boston. And you can still read the informational plaques around the site.

The monument marks the spot where in June, 1775, British forces attempted to take a fortified hill from Colonial army and although they eventually succeeded, the British had 1,000 casualaties (out of 2400 men) while the Colonials lost 300-500 men to death, wounds, or capture (out of 1400-1800 men). It proved that the Colonial Army could hold its own against the much larger, better equipped, and better trained redcoats. The National Park Service has an excellent recap of the battle on its website.

The famous battle cry “ Don’t fire until you see the whites of their eyes!” is thought to have been said during this battle as the colonists were running low on ammunition.

The small Bunker Hill Museum is just across the street from the main entrance to the grounds and, from what I hear, is pretty good. (We got there after it closed.)

Both the museum and the monument are free to visit and are open 10-5 in the winter (hours are slightly longer in the summer). The park around the monument is always open. To climb the monument’s 294 steps to the top, you will need to check with the ranger at the lodge adjacent to the monument and be there no later than 420 pm.

2.USS Constitution aka “Old Ironsides”

The oldest commissioned warship still afloat in the world was a big hit with everyone, despite the drizzling rain we encountered that day. There are 2 parts to this site- the ship itself and the nearby museum, both of which are free (although the museum asks for donations). Everything is located in the Charlestown Navy Yard, a National Park Service site that operated as a working naval yard from 1800-1974.

The USS Constitution is staffed by US Navy personnel who give the tours of the ship’s 3 decks and are available to answer questions. The leader will give a short talk about the highlights on each deck, then you have a few minutes to walk around and take pictures on each deck before moving on. You must be able to climb down the ship’s stairs (steep and with a rope railing) to reach the bottom 2 decks so not super accessible for those with mobility issues or in a stroller. Tours are scheduled every 30 min and last about 30 min although you can stay a little longer to take more pictures if you wish.

The ship was built and launched in 1797 in Boston at docks not far from her current berth. So she is, in a sense, home. She is undefeated in battle and responsible for the capture of several British naval vessels during the War of 1812. The nickname “Old Ironsides” came from a British sailor who was amazed how their cannonballs just bounced off her thick wooden hull.

The associated museum was a surprise highlight for us. It had lots of interactive exhibits that the kids were completely obsessed with, plus a short film about the history of the ship. The kids loved playing a large wooden version of “Battleship” with the 2 sides being either an American merchant ship or a French naval vessel/ British naval vessel/ Barbary pirate out to capture them. No joke, they played this for at least 30 minutes. Again, this was only possible because there were only about 10 other people in the museum while we were there, a huge difference from visiting in the summer.

The museum is a privately run non-profit that operates thru donations so while you don’t have to pay for admission, they ask for $25- $50 per family. It was money well spent for 2 hours of fun. We could have spent even more time but we got hungry. Next time, we will plan on having an early lunch and then visiting.

The ship is open in the winter from 10-4, Wed- Sun (summer hours are longer). You must have a picture ID if you are over 18 to get on the ship and everybody has to pass thru a metal detector and bag screening. Tours are first come, first served.

The museum is open daily from 10-5 and no screening required. Both the ship and the museum are closed on the major holidays of Thanksgiving, Christmas, and New Year’s but are open on the 4th of July. The ship is also closed on MLK Day.

Also in the Charlestown Navy Yard, at a pier adjacent to the USS Constitution, you will find the USS Cassin Young, a Fletcher-class destroyer built in 1943. She fought in 7 Pacific battles and survived 2 Kamikaze hits. Unfortunately, the ship is not open for tours from November until April, but you can go right up to her on the pier while the Naval Yard gates are open.

If you don’t get a chance to visit during the day, you can still get a good view of the USS Constitution at night from the surrounding piers that are open 24 hours.

To get back to downtown Boston from Charlestown after seeing the USS Constitution and Bunker Hill, you can either walk across the Charlestown Bridge or you can take the MBTA ferry for a fun scenic and cheap tour of Boston Harbour.

The ferry leaves from the Charlestown Yard Naval Terminal which is on the opposite side of the Cassin Young from the USS Constitution. The ferry takes you to Long Wharf by the New England Aquarium. Tickets are $3.70 adults/ kids 11 and under ride free. You can buy tickets at the booth on the pier. Ferries are every 15-30 min from 645 am- 815 pm weekdays and 1015 am- 615 pm on Sat/Sun. If you bought a 1 day or 7 day CharlieTicket for the T (more on that at the end of this blog), it is good for this ferry service as well.

If you are looking for a place to eat in Charlestown, there are 3 places we liked-- Warren Tavern, Blackmoor Bar and Kitchen, and Brewer’s Fork. See my paragraph at the end of this blog on “Where To Eat” in Boston.

3. Copp’s Hill Burying Ground

This is a graveyard that turned out to be more interesting than we thought it was going to be. Several famous Bostonians are buried here, such as Increase Mather and his son Cotton Mather, both of who were influential Puritans in the Massachusetts Bay Colony. Cotton Mather played a role in the Salem Witch Trials and not in a good way.

The kids particularly enjoyed finding the graves marked with medallions indicating that a Boston Tea Party participant is buried there. And they really liked the bullet marked grave of Daniel Malcolm, a reputed smuggler and passionate opponent of the British Revenue Acts. During the British occupation of Boston, redcoats took potshots at his grave for luck. Malcolm requested he be buried 10 feet deep to prevent his enemies from disturbing his body, so I guess he knew how much the British hated him.

The British used Copp’s Hill to shell Bunker Hill with cannonballs during that namesake battle. You can see the obelisk from here which gives it a nice reference point to imagine the historic scene.

The burying ground has several really informative signs so try to walk around and read them if you can. I particularly liked learning about the free African Americans buried there, especially Prince Hall, a Revolutionary War soldier, anti-slavery activist, and founder of the world’s first black Freemason lodge.

Just across from the entrance to Copp’s Hill Burying Ground is a very skinny house that is helpfully marked with a sign outside “Skinny House.” At 4 stories tall, 10 ft wide, and only 1,166 sq ft, it definitely is Boston’s undisputed skinniest house. Built in 1884, it is also a spite house.

Legend has it that while the one brother was off at war, the other built his large house on their shared land, leaving his brother only a sliver to call his own. But he purposefully built on it anyway to ruin the view and block the sunshine from his brother’s house. The kids were fascinated with this. I was fascinated that it sold for $900,000 in May of 2017.

* Interesting Trivia not on the Freedom Trail- If you look out to the harbour from the edge of Copp’s Hill, you can see a playground and athletics fields next to the water. This is the site of Great Molasses Flood, also called locally the Boston Molassacre. A humongous storage tank of molasses exploded in January of 1919, sending a wave of sticky goo 25 ft high and traveling at 35 mph. It flooded several blocks to a depth of 2-3 ft and killed 21 people, several horses, and injured another 150 people. Many victims took hours to free as January temperatures condensed the goo.

The catastrophe left the area with a massive cleanup that lasted weeks and eventually included all of Boston as cleanup crews and curiosity seekers tracked molasses all over public transportation and into their homes. Apparently everything a Bostonian touched afterwards was sticky and the basements of the flooded homes still smell like molasses today when it gets hot outside. The “I Survived” series even has a book about it because of course they do. Elementary school kids will love reading about it. “#19 I Survived The Great Molasses Flood, 1919” by Lauren Tarshis.

4. Old North Church

Boston’s oldest church building (1723), this is the steeple from which the lantern “one if land, two if by sea” hung, made famous in Longfellow’s poem “Paul Revere’s Ride”.

We opted to pay admission for Old North Church because we wanted to take a break by that time on our walk and go inside to warm up. I am so glad we did. There was hardly anyone else inside the church and the super nice attendant answered a billion questions from the kids who were intrigued by the individual pew boxes-- that people could buy them and decorate them as they wanted. They even had one decorated as it would have been back in the day, with red silk and heated foot boxes.

The admission wasn’t too bad- $6 an adult, $2 a kid so $20 for our family of 6. It is not covered under any all inclusive or multi-attraction Boston passes.

We did not pay the extra $2 a person for the 30 minute “Behind The Scenes” tour mostly because we didn’t think we would have time. In retrospect, I wish we had done it because the kids were disappointed they could not climb the stairs to see the bells or go down to the crypt below the church.

The church covers more than just its lantern hanging moment of fame; many important patriots and even the British general during the revolutionary days, Thomas Gage, attended church here. Each box pew has a plaque detailing something interesting about its owner or the sequence of the events leading up to Paul Revere’s ride.

* In between Old North Church and the next stop on the Trail, the Paul Revere House, you will walk by a large statue of the man himself on horseback. The statue is nice and all but the most interesting thing about it is that when any of Boston’s sports teams are playing in a championship or people just feel like it, he gets a spiffy team shirt. (He also gets dressed up for major holidays too.)

5. Paul Revere House

A small house you could could walk right by if you weren’t looking for the sign outside. This is Revere’s original house, saved from demolition in 1902 by his great grandson. We almost skipped it (because it also had an entrance fee) but again, I am glad we did not.

The Paul Revere House has been restored and furnished to be historically accurate and it is really well done, from the fake food on the table to the old playing cards on the table upstairs. It is self- guided with plenty of informational signs and a museum interpreter on each floor to tell you what you are looking at.

This is another site that I found to be much better visiting in the winter than in the summer. Besides the fact that the house is not air conditioned, we were the only people in the house for a good while, meaning we had plenty of time to ask questions of the interpreters and read all the signs without having to push thru crowds.

There is a small museum attached that covers more of the details of Revere’s midnight ride. Turns out Longfellow took some creative liberties with the actual events of that night, i.e. Paul Revere did not ride off alone and he was captured by the British before he made it to Concord.

Admission is $5 for adults and $1 for kids (cash only!) and I felt it was well worth it. The kids enjoyed looking at the period furniture and gawking at how 5 kids slept in one small room with 1 double bed. That alone was worth the entrance fee.

The Paul Revere House is open 930- 415 in the winter. It is closed on Mondays in Jan, Feb, and March as well as Thanksgiving, Christmas, and New Years Day.

*Between the Paul Revere House and Faneuil Hall, you will go by the New England Holocaust Memorial, a somber and thought provoking installation consisting of 6 glass towers. There is steam billowing out of the vents within each tower, meant to evoke the gas chambers of the concentration camps. Inscribed inside each tower is a quote from survivors and witnesses to the Holocaust while the outside of the glass panels is inscribed with 17,000 7 digit numbers like the numbers tattooed on victims’ arms.

My 10 year old nephews are studying WW2 in school so even they understood the significance of the memorial. It was certainly a change of pace from the Freedom Trail’s emphasis on the colonial years and was one of the most memorable moments of the day.

6. Faneuil Hall

Built in 1741 by merchant Peter Faneuil as a gift to the city, the ground floor was a popular marketplace for the growing colony and the Great Hall upstairs was the site of many of speeches against “taxation without representation” by leading patriots such as Samuel Adams.

* Pro- Tip - After much asking of locals, I believe you can pronounce it “FAN-el” (rhymes with flannel) or “FAN- you- uhl” (rhymes with the Samuel who gave the speeches here). There does not seem to be a consensus except that “Fan-NEE- uhl” is right out. That was my attempt on my first visit years ago and there was much laughter.

The National Park Service Visitor Center is on the first floor of Faneuil Hall and it has a gift shop, a help desk, tons of brochures about historic sites in Boston, and some history. This is where the old marketplace was located.

Look for the big printing press on the east side of the building on the first floor. If you are lucky, a period dressed docent will give a demonstration of how the Declaration of Independence would have been printed back in the day. Our demonstrator even let my 12 year old niece work the handles. This was a huge hit with the kids. He was full of interesting trivia and very personable.

The Great Hall upstairs is where the colonists had their meetings. Even after the Revolution, Boston’s city government continued to meet there until it became too small. The Hall was still used as a public meeting place for the community though, as abolitionists, suffragists, etc all had meetings here. JFK gave a campaign speech in the Hall in 1960. It is used by the city for immigration ceremonies today.

The marketplace was so successful, the city voted to expand it in the 1820s, which is why you will find Quincy Market just behind Faneuil Hall. More expansion lead to North and South Market Buildings on either side of Quincy Market, plus a ton of temporary pushcart vendors set up in the surrounding pedestrian areas (when the weather is nice enough). It is all collectively known as Faneuil Hall Marketplace.

The marketplace is a fun place to go shopping, even if many of the shops are exactly the same as in your mall at home and it is not exactly cheaper at this prime location. But you will find some Boston specialties, such as Best of Boston, which carries all kinds of souvenirs, food, and clothing. If you have a tweenager, chances are they will never want to leave this area. Which is fine because you can easily indulge your inner foodie at the long hall of takeaway counters in Quincy Market. Lobster rolls, bakeries, noodle shops, “chowda” specialists, etc, can all be found here.

Faneuil Hall is open daily 9-5 except Thanksgiving, Christmas, and New Years Day. The Great Hall upstairs is sometimes closed to visitors for city sponsored events. The Faneuil Hall Marketplace is open 10-7 M-Th, 10-9 Fri and Sat, and 12-6 on Sundays in the winter (summer hours are longer). The restaurants in the marketplace often have their own hours.

* The pedestrian areas around Faneuil Hall and the markets will be filled with performers on any day with halfway decent weather. Some of them are really good-- like the dancers we saw with skateboards and their own stereo equipment. Some were not so good, like the bongo drummer who only knew one rhythm. Regardless, the kids were fascinated so we spent a lot more time at Faneuil Hall than we planned, so keep that in mind.

7. Boston Massacre Site and 8. Old State House

The Boston Massacre took place right outside the Old State House so it is easy to combine these 2 stops on the tour. They are close to Faneuil Hall as well. Because of time constraints and the kids being a little museum-ed out, we did not go in the Old State House on this trip.

Built in 1713 to house the offices of the Massachusetts Bay Colony, the Old State House is the oldest surviving public building in Boston. It also held the Council Chamber of the Royal Governor, the Assembly, and the Massachusetts Supreme Court. You can go thru the recreated rooms of the Council Chamber and see the exhibits covering the Boston Massacre and the founding of the Massachusetts Bay Colony.

The best thing to do in the State House is participate in the 25 minute docent tours that are included with admission. Take advantage of the lack of crowds in the winter so you can really hear what they are saying and ask questions. If you aren’t up for the tours, then I would probably skip the entrance fee, especially if you have gotten to explore some of the other historic sites on the Trail and feel like you are good on your colonial history.

There are 2 docent-led tours: a Boston Massacre Tour and an Old State House tour. The scheduled times follow each other so it is easy to do both. Check the website for your specific dates, but when we were there, the first Old State House tour started at 10 am and the first Boston Massacre tour was at 1030 am. The next tours were at 12 pm (and 1230), 2 pm (and 230), then the last tours at 4 pm (and 430). Tours take place 7 days a week.

The Old State House is open from 9-5 (6 pm in summer). Admission is $12 adult and free for kids under 18.

If you only care about the Boston Massacre and the kids are over visiting any more museums, then skip entering the Old State House and look for the large medallion inset in the sidewalk just in front of the building. This marks the spot near where the event happened. (The shooting actually took place in the middle of the busy intersection next to the marker so you can see why they moved it here.)

The medallion has 5 stars on the bronze outer ring to commemorate the 5 victims of the massacre and 13 cobblestone spokes for the 13 original colonies. Look for the information plaques nearby to learn more about the massacre.

9. Old South Meeting House and 10. Old Corner Bookstore

These two sites are catty-corner to each other so it is easy to see them together.

Old South Meeting House was built in 1729 as a Puritan meeting house (which functioned as a church as well). Several famous Bostonians were members- Sam Adams, William Otis, young Benjamin Franklin and his family, and the African- American poet Phyllis Wheatley.

Meetings too large for Faneuil Hall were held here, including the famous one on December 16, 1775 to protest the hated “tea tax.” When a compromise could not be reached, Sam Adams gave the signal from the Old South Meeting House to begin the Boston Tea Party.

During the British occupation of Boston, they destroyed the interior of the church and turned it into a place to practice jumping their horses. The Brits knew its importance to the people of Boston and this was not an inadvertent act.

The interior of the Old South Meeting House is fairly similar to Old North Church with its pew boxes and decor except that the exhibits on the walls here are focused on the Boston Tea Party rather than Paul Revere. But general revolutionary history is also covered, plus there is a small exhibit on Phyllis Wheatley, an enslaved poet who published a book of poems in 1773 and counted George Washington as a reader.

Like other sites on the Freedom Trail, we enjoyed visiting in winter versus summer as you had plenty of time to look at the exhibits and ask questions of the docents without feeling rushed.

Admission to Old South Meeting House is minimal- $6 adult, $1 for kids (free under 5). Open 10-4 in winter (930-5 in summer) and closed Thanksgiving, Christmas Eve, Christmas, and New Years. Also closed on Tuesdays in February.

Old Corner Bookstore is important because not only is the building pretty old (1718), but it housed the publishing house of Ticknor & Fields from 1832- 1865. These were some of the most important publishers in the world at the time, publishing Walden and The Scarlet Letter, as well as the Atlantic Monthly, which introduced the world to writers such as Lousia May Alcott.

Ralph Waldo Emerson, Henry David Thoreau, Nathaniel Hawthorne, Oliver Wendell Holmes, Henry Wadsworth Longfellow, Richard Henry Dana, and many others, gathered at the nearby Parker Hotel (across from the Latin School a block away) to discuss their works and exchange literary gossip at what they called The Saturday Club that met at 3pm on the last Saturday of each month. The gatherings led to the creation of the Atlantic Monthly magazine. So between this building and the Parker Hotel (now an Omni hotel), a lot of very witty people have trod.

The Old Corner Bookstore is now a Chipotle which is either a travesty, a hilarious take on the march of time, or a convenient lunch/ dinner stop on the Freedom Trail, depending on your outlook.

11. Boston Latin School Site/ Benjamin Franklin Statue

Just around the corner from Old South Meeting House is location of the Boston Latin School when it opened in 1635. It was America’s first public school (and it is its oldest as well as the school is still operating at its current location in Fenway). The mosaic hopscotch board on the sidewalk marks the spot where the school stood until 1844 when it moved farther west to a bigger building.

Benjamin Franklin was a student at the school, which offered free education to boys (girls were not admitted until 1972). Four other signers of the Declaration of Independence were also alumni: John Hancock, Samuel Adams, Robert Paine, and William Hooper. Franklin’s statue stands near the mosaic, just inside the fence.

Legend has it that when word spread around Boston about the battles in Lexington and Concord, the headmaster at the school announced “Books closed. School is done and war has begun!”

*Fun Kid Stop- In the same little plaza in front of the Old City Hall as Ben Franklin’s statue, you will see a lovely little donkey sculpture that the kids will immediately gravitate to. Feel free to climb on it, it is meant for that. The donkey has a strange history that you won’t find on any sign nearby. I had to look it up when we got back home. The story is definitely worth a read for its convolutedness.

12. King’s Chapel and Burying Ground

King’s Chapel was founded as the first Anglican church in America in 1686. The current Georgian building dates from 1754 and the bell tower rings a bell cast by Paul Revere so plenty of history here as well. After the Loyalists departed for Canada in 1776, the building became America’s first Unitarian church which it is still today.

The interior of the church is a slightly more ornate version of Old North Church and Old South Meeting House, with the familiar pew boxes and elevated pulpit.

It is free to enter but they ask for a small donation ($4 an adult). Look for the brochures for a self- guided tour and for the interpretive displays about important events in the church’s history or notable congregants.

The church is open in the winter Friday- Monday 10 am- 4 pm (130 pm- 4 pm on Sundays).

If you really want to get the most out of your visit, do the 40 minute Bell & Bones tour that takes you up to the belfry and down to the crypt. We did not get a chance to do this, but I have heard it is very interesting and that the guides are really into it. The tour costs $7 adults/ $3 kids and you need to be over 10 years old, able to climb steep stairs, and not suffer from claustrophobia. Tour times are 11am, 12 pm, 2 pm, and 3 pm Fridays- Monday (Sundays 2 pm and 3 pm.)

The burying ground next to the church is the oldest in downtown Boston so it makes sense that Mary Chilton, the first woman to set off the Mayflower, is buried here along with a lot of other notable Bostonians. My favorite part is the straight rows of headstones which apparently was done in the early 1800s to make it look pretty and has no correlation to who is buried underneath.

13. Granary Burying Ground and 14. Park Street Church

Yet another cemetery, this is a much bigger graveyard than King’s Chapel and has the remains of some of Boston’s most famous people-- Paul Revere, John Hancock, Samuel Adams, and all 5 of the Boston Massacre victims.

The Granary Burying Ground is both pretty and free, which makes it a nice stop on the Freedom Trail if the weather is decent. It was not for us, being a cold and super windy day, so we peeked in and kept going. It is open from 9-4 in the winter.

Next door to the Granary Burying Ground, on the site of the old granary that gave the place its name, is Park Street Church. This congregationalist church, built in 1809, is on the Freedom Trail but is only open from June- Aug so we did not go in.

15. Massachusetts State House

Another Charles Bullfinch designed building in Boston, the State House is famous for its gold dome that was originally coppered by Paul Revere in 1802. The State House is open weekdays 9-5. Enter through the gates by the statue of General Hooker (to the right if you are looking at the front of the building, at the corner of Park and Beacon). Go up to the 2nd floor to the Information Desk.

Free, 45 min tours are given by a docent from 10 am - 330 pm. These are rated pretty highly and take you through the beautiful atrium and both the House and Senate chambers (if they are not in session). Be sure to look out for the “Sacred Cod” in the House chambers where it has been hanging over them since 1784.

We skipped this as well because we walked by the State House on a Sunday so it was not open. But I have done the tour in years past and enjoyed it although I would not say it is a must do. But it is free and might be a good stop if you need a place to warm up for awhile.

16. Boston Common

America’s oldest public park, Boston Common originally began as a grazing pasture, militia training field, and public hanging place before becoming more like the garden we see today during the 1800s.

Always open and free admission, the Common is one of my favorite places in Boston. It is a good opportunity to let the kids run a little without worrying about cars, besides just being a lovely open and green area after all that concrete. Even in winter, it can be a nice place to walk around as long as the wind isn’t too bad. Check out the skating rink and watch the people if you aren’t into trying it out yourself.

The Frog Pond is a kiddie spray pool in the summer that turns into an awesome ice skating pond from Nov- March. Anyone over 58 inches is $6, below that is free.

Skates cost $12 adults/ $6 kids and they even have big blue seal things that kids can push around to help them with their balance. Or they can just ride the seal while you push them around which I am guessing is how that usually ends up. You can see one of the seals in the picture.

We did not skate as we were already traveling with a kid who had a broken bone and did not feel like trying our luck. But it is something that is usually a big hit with the kids.

If the weather is okay, then walk over to the west side of the park, across Charles Street, to where the big pond is. This is actually Boston Public Garden, the more formal garden compatriot to Boston Common. At the northeast corner of the gardens, near the entrance at the corner of Beacon and Charles streets, you will find the popular Duckling sculpture, honoring McCloskey’s famous book Make Way For Ducklings. The book was set in Boston Public Garden so it makes sense. The ducklings, like so many statues in Boston, often get decked out in Boston team jerseys, especially when a championship is happening. They also like their holiday wear.

Other Tidbits From Our Boston Trip- Transportation, Lodgings, and Restaurants

Getting Around Boston In Winter

We walked everywhere on most days since we were staying downtown and sightseeing mostly in downtown as well. Boston is a very walkable city and we generally spent 20-45 minutes walking, then hopping into a historic site, museum, or restaurant for awhile before heading back outside to walk to the next place.

Ride Share

For places too far away to walk (Cambridge or Fenway for example) or getting back and forth to the airport, we used Uber/ Lyft and public transportation. Ride sharing is very popular in Boston and you won’t have any problem finding a ride. Short rides around the city will cost you $8-$10 while the airport might cost $15-$40 depending on time of day and distance.

* Uber is far more expensive than public transportation. I spent more in one day on 3 short rides on Uber ($30) than my whole 7 day CharlieTicket cost ($22.50). Plus, kids 11 and under ride for free on public transport.

Public Transportation

Boston’s has a really good public transportation system of subway, buses, street trams, commuter rail, and ferries. The subway system is known as the “T” and is the one you will use the most as it has lots of stops downtown. There are 2 types of tickets- a CharlieCard (this is a plastic rechargeable card used by locals and is not something you will need) or a CharlieTicket (a durable paper card for single fares and for short term visitors- this will be what you get).

Each ride on the subway is $2.90 no matter the destination or time of day. Kids 11 and under ride free. Buy a CharlieTicket at one of the fare machines in each station after deciding how much money you want to put on it. You can choose a single fare or multiples thereof. Unlike, say New York City, you cannot use a CharlieTicket for more than one person so everybody 12 and older needs their own ticket. The fare machines are really easy to use and have pretty clear options spelled out. Machines take cash, credit, and debit cards. You will then feed your CharlieTicket into the turnstile gates to enter the station.

There are several videos on YouTube that demonstrate the fare machines, the turnstiles, etc. Just make sure it is a fairly recent video as the system keeps changing.

Getting the 1 Day or 7 Day Pass for Public Transportation

If you think you are going to ride the T at least 8 times during your stay, then go for the 7 day pass for $22.50. It gets you unlimited travel on the subway, bus, Charlestown ferry, and inner commuter rail zone.

If you are here for only one day, look at the 1 day pass for $12.75. Even if you don’t quite make it pay for itself, it is nice to be able to go straight to the gates and skip the fare machine. The passes are issued on a special CharlieTicket that are time and date stamped.

Getting Back and Forth From the Airport

It is quite easy to get into town from the airport using public transportation. Boston has free airport buses that take you to 2 subway stations (why don’t more cities do this?!) and there is no special surcharge for subways to and from the airport.

Catch the Silver line (which is bus despite being colour coded like the subway lines) from the airport to South Station for the Red line (this is a free transfer so you get to ride the Red line for free too). Or take a Massport bus (either # 55 or # 22) to the Airport Station for the Blue line (not a free transfer and you will have to buy a CharlieTicket to get on the Blue line). All of the buses pick up right outside baggage claim in their designated area for each one, just look for the signs.

Half of our family took an Uber to our hotel in Charlestown from the airport and half took the airport bus/ subway combo. The Uber only beat the train people by 5 minutes and that’s because we had to walk from the station.

Going to the airport from downtown is just as easy but if you are taking the Silver Line from South Station, you will have to pay a normal fare as the ride is only free coming from the airport, not going to it. The Massport shuttles to and from the Airport Station (blue line) are always free.

Learn more about using public transport to/ from Logan Airport here.

Where To Stay In Boston

This can depend on lots of factors: Do you have a car? How many people are in your group? Do you want to have a kitchen or free breakfast so you don’t have to eat out every meal?

Thanks to excellent public transportation, I don’t generally have a car when I visit Boston so I can stay downtown without worrying about paying $40 a day in parking fees. If you have a car, you are probably going to want to stay a bit farther out and use the T or commuter rail to get into the city everyday.

Anywhere downtown is going to be convenient enough for the sites on the Freedom Trail, just try and not go farther out than Interstate 90. It is nice to be able to nip back to the hotel during the day for a break or nap times or to grab an extra jacket or gloves if needed. You will find plenty of hotels to choose from no more than a mile from Faneuil Hall or 1 or 2 stops on the T.

*Some of these links are affiliate links, meaning we may get a commission (super small but every bit helps) but it doesn’t affect the price for you at all. We only recommend places if we have stayed or would stay there with our own families. Full Disclosure Statement.

Where We Stayed

We stayed in the Residence Inn in Charlestown, just across the bridge from downtown and next to the USS Constitution. This was a fabulous hotel for 2 adults and 4 kids because it had 2 bedrooms (1 King, 1 Queen) with 2 bathrooms and a common room between the bedrooms with a pullout sofa (double). Try and get rooms overlooking the marina as the sunrise is gorgeous.

Our room also had a full kitchen and the hotel offered an extensive free breakfast (waffles, scrambled eggs, sausage, yogurt, fruit, oatmeal, baked goods, etc). Between the breakfast and being able to refrigerate and reheat leftovers, we saved a good bit of money feeding 4 kids.

We also stayed at the Hotel Indigo across from TD Garden for part of the trip (we added more people to the group and now needed hotel rooms with 2 beds each). The Indigo was also a nice hotel that I would stay at again. It is a great central location steps away from North Station so super convenient for the T.

The hotel is clearly in an older building that they have redecorated into a more modern boutique hotel so it has some quirks like tiny elevators and squeaky floors. The furnishings were comfy though and brand new and the rooms were spacious. The kids were sold when reception gave them each a humongous brownie one afternoon.

We had 2 rooms (not adjoining) at the Hotel Indigo-- a 2 queen room that had enough space to put a kid on the floor and a king suite with a separate living area containing a pullout sofa, table, 4 chairs, and a desk. The pullout sofa was small and we had just one kid in it but the room itself was much larger than I was expecting. It became the gathering place for our family group of 7.

Each of our rooms at the Hotel Indigo had a fridge and coffee maker but no microwave. The hotel does not offer free breakfast, but there is a coffee/ pastry place next door that we frequented.

Other Places to Stay In Boston

Try to stay as close to center of the peninsula as possible, not going farther south than Interstate 90 and not too far across the Charles River. It is worth it to be within walking distance or a short subway ride of the Freedom Trail and the other main sites downtown.

Where To Eat In Boston

Boston is loaded with good restaurants everywhere you turn and they run the gamut from takeaway counter to fancy dress. You can also find a fair amount of tourist traps as well, especially around Faneuil Hall but even then, I am often surprised by the quality of the meal even if I am wincing at the price. When in doubt, aim for a tavern, especially one that looks like it has been around awhile and has lots of locals.

Here are my specifics from this last trip:

The North End

Much of this area is basically Little Italy and while some of it is clearly for the tourists, it is also the kind of place where you see locals gathering outside the bakery at 9 pm for fresh cannolis. Hanover Street is the main drag through Little Italy but all the surrounding streets will have places.

Mike’s Pastry is the famous bakery on Hanover but if the line is out the door or you don’t have cash, try Bova’s Bakery just one block away, at the corner of Prince and Salem St. It is open 24 hours a day in case you get a midnight tiramisu craving. It also takes credit cards in case you are like me and never seem to have cash on you.

For an awesome Italian dinner, try Riccardo’s Ristorante, catty corner to the Paul Revere House on North St. We went there with our family party of 7, including 4 kids, and they made us feel right at home. You can tell it is a family-run place.

Riccardo’s didn’t have a kids menu per se but they offered to make any of the dishes into a smaller portion. We just ordered a bit of everything and shared. It was one of our favorite places on the trip.

Open for dinner M-Th, lunch and dinner Fri-Sun. You might need reservations in summer, but in January, we walked right in on a Saturday night.

Around Faneuil Hall

The Green Dragon Tavern is on the Freedom Trail and is one of many taverns lining the cobblestone streets near Faneuil Hall. I have usually avoided these places in the past, thinking they were too touristy, but hungry kids and a warm, cozy interior convinced me to stop on this January trip. And it was great. Not cheap, but we got the cup of soup which was filling and warm on a cold winter’s day and only $6. The kiddos ordered off the kids menu, which was your typical grilled cheese, pasta, chicken tenders, etc. with drink and fries all in for $8. Throw in a decent selection of New England beers, and we were happy as clams.

The kids enjoyed reading about the history of the original Green Dragon Tavern-- the British plans for marching on Lexington and Concord were overheard here. Not sure how accurate that is but it made for interesting reading. The tavern is located on the picturesque cobblestone Marshall Street, just off Hanover Street and by the New England Holocaust Memorial.

* Just up Marshall Street from the Green Dragon is the Boston Stone, a large millstone embedded in the wall of a building and inscribed Boston Stone 1737. Nobody really knows why the stone is there but people have lots of ideas. The most likely is that somebody in the 19th century created it as a phony landmark in imitation of the London Stone to drum up business. The fact that marketing is still just as shady as it has ever been makes me laugh.

There are several historic places right around the Green Dragon that are about the same in price, atmosphere, and historic claims: The Bell In Hand Tavern (America’s oldest tavern- 1795) and the Union Oyster House (America’s oldest restaurant- 1826) are probably the two I would choose.

If you don’t care about history or are looking to save some money, head to Quincy Market (just behind Faneuil Hall) and the abundance of takeaway stalls in its famous food colonnade. You will find just about anything you want there and there is a section in the middle of the market with tables.

In Charlestown

In this charming neighborhood just a short walk from downtown Boston and home to the Bunker Hill Monument and the USS Constitution, you can find a couple of good choices.

The Warren Tavern is very near Bunker Hill and makes an excellent place to have a meal after you have seen the monument. It was established in 1780 and calls itself Massachusetts oldest tavern, making it older than the Bell in Hand but I am sure that there is some technicality that makes them both right. Anyhow, it was named for Dr. Joseph Warren, the famous Revolutionary leader and doctor who was killed during the battle of Bunker Hill. It is a cozy place with a low roof and warm interior that was a welcome stop on a windy night.

Prices were pretty typical for a restaurant in Boston but my fried haddock sandwich was well worth its $15 price tag. It was huge. Warren Tavern does have a basic kids menu as well and the place is full of locals, from people watching the game at the bar to families grabbing a bite to eat. It was a wonderful atmosphere. The tavern can get busy so try to go during off peak dining hours. Luckily in winter, it is less of an issue than during the summer.

The Warren Tavern is open for lunch and dinner everyday plus brunch on Sat/Sun. On the corner of Pleasant and Main St, 2 blocks from the Bunker Hill Monument.

* The tavern was also a Freemason Lodge, like so many other historic buildings in Boston, and so was frequented by leading patriots of the time, like Paul Revere, who were all apparently Freemasons. George Washington also came here in 1789 to dine with a friend. (Washington was also a Freemason, just pointing that out as I was unaware just how many of our founding fathers were members).

Blackmoor Bar and Kitchen was super close to the Residence Inn where we staying so we ended up eating there twice. Serving New American food in a big modern interior, this place is family friendly and can handle large groups. They had a basic kids menu, a fantastic nacho appetizer that could feed all of us, and an extensive beer list. Two thumbs up. Open for lunch and dinner everyday, plus brunch on Sat/Sun. On the corner of Washington St and Chelsea St by the Charlestown Bridge. Near the USS Constitution.

Brewer’s Fork is also close to the USS Constitution (o.2 miles from the museum heading north) and has great pizzas as well as sandwiches, small plates, and an extensive craft beer list (and pretty good wine list as well). They don’t have a specific kids menu but is family-friendly. Plus, it’s pizza.

To get back to downtown Boston from Brewer’s Fork, you can either walk across the Charlestown Bridge or you can take the MBTA ferry. It leaves from the Charlestown Yard Naval Terminal and takes you to Long Wharf by the New England Aquarium. $3.70 adults/ kids 11 and under ride free. You can buy tickets at the booth on the pier or use your one day or 7 day pass. Ferries are every 15-30 min from 645 am- 815 pm weekdays and 1015 am- 615 pm on Sat/ Sun.

Other Tidbits We Learned

• None of the all inclusive passes or multi-attraction passes you can buy for Boston really make sense if you are just doing the Freedom Trail because the entrance fees (what few there are) are pretty minimal, especially for kids. Now if you are thinking about doing the Freedom Trail plus a big attraction like the Museum of Science or the Aquarium, then a pass starts to make more sense. Read my other blog “ What To Do In Boston In January” for a full breakdown of the available passes.

• Do not criticize the Patriots. The rest of the country may hate them but the people in Boston have very little sense of humor about them not making the Super Bowl. It is like joking with a TSA agent about having a 6 oz liquid in your carry-on, zero chill.

• Print out or download the PDF brochure from the Freedom Trail and let the kids take turns driving, metaphorically speaking. The inlaid brick trail makes it easy for them to lead the way, and they will have fun playing tour guide and reading the descriptions of each site aloud for everyone.

• It is easy to self-guide on the trail but if you would like to have a guide, use one from the Freedom Trail Organization. They offer a number of guided tours everyday, each focusing on a different aspect of the Freedom Trail, although some only operate during certain months (ie African American Patriots is during February) or during the busier summer months. The traditional tour, Walk Into History, is offered year round, lasts 90 minutes, and covers Boston Common to Faneuil Hall (so no Paul Revere House, Old North Church, USS Constitution, or Bunker Hill). Tours cost $14 adult/ $8 kids 12 and under/ free under 6.
  

We hope you love the Freedom Trail as much as we did and that Boston’s weather treats you kindly on your visit. It really is a fabulous city and one of my favorite tourist destinations. This was my first time visiting in January and I will have to say that while I missed strolling along the Charles River enjoying a warm day or the flowers in Boston Common, the lack of tourist crowds elsewhere more than made up for the colder weather.

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