Looking for a destination for Fall Break that is both beautiful AND rich in history? You can’t go wrong with discovering all of the seriously cool things to do in Boston in the fall (or any time of the year for that matter).
Would you agree that it can be expensive to travel and see the sites at the same time? Not to worry, Boston offers a variety of fun and family-friendly activities that are perfectly free. You’ll find some free options below and some that require an entrance fee—sparking the perfect balance for your travel budget.
25 Seriously Cool Things to Do in Boston
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Our family’s Fall Break excursions seem to have a little more historical significance attached to them over the warm weather and beaches my girls are usually craving for Spring Break after a long and cold winter.
Perhaps the allure of Fall Foliage also inspires our family travel adventures.
Hmmmm, or maybe that’s just me and my husband is awesome enough to oblige.
You will want to pack umbrellas, gloves, puffy jackets, and scarves. The weather could surprise you with glorious fall days or the chilly rainy days as our family experienced.
In fact, we invested in gloves and umbrellas once arriving in Boston for our family travel adventures just to stay warm and dry before setting off to explore the Freedom Trail. With all of the rain, each one of us needed our own umbrella.
Did you know that Boston is ranked by US News among the top 30 Best Places to Visit in the USA in 2023-2024? You should go.
1. The Freedom Trail
If you are looking for a significant historical experience while searching for things to do in Boston, sites along the The Freedom Trail should whet your whistle.
The Freedom Trail is 2.5 miles of red-bricked path along the sidewalks in Boston. You can pick up one of the Freedom Trail Official Online Brochures for a self-guided tour along the trail.
Put on your walking shoes (’cause you’ll be doing a lot of it) and step back in time.
The official Freedom Trail starting point is at Boston Common and continues the 2.5 miles to the USS Constitution Museum where it ends. If you start in the middle as we did at Faneuil Hall, you will need to double back on your tour.
You can take a self-guided tour or find a guided tour to join.
Map of The Freedom Trail
2. Faneuil Hall
With its sometimes controversial history, Faneuil Hall has stood in downtown Boston for over 275 years. It was built in 1742 as a market place and a meeting hall that hosted gatherings, protests, and debates.
It’s legacy continues today. Though Faneuil Hall is not the beginning of the Freedom Trail, you can still begin your tour of the Freedom Trail here.
Faneuil Hall, owned by the City of Boston, operates as a historic site and visitor center by the National Park Service.
The Visitor Center is located on both the first floor (market) and the lower level of the building. The second floor houses the Great Hall.
If you are looking for cool things to do in Boston around Faneuil Hall, check out the Faneuil Hall Marketplace. The Marketplace is made up of four buildings: Faneuil Hall, Quincy Market, North Market, and South Market.
Today, you’ll find a variety of historic artifacts, top-rated restaurants, local artisans selling unique, hand-crafted wares, and throngs of visitors. Faneuil Hall Marketplace is touted as America’s first open marketplace. It is one of the many fun things to do in Boston.
Check the National Park Service website for current hours and closings.
3. Boston Common
Boston Common is America’s oldest public park. After its purchase from William Blackstone in 1635, the grounds were commonly used for grazing sheep and cattle. It evolved as a training field for militia to a British Army camp to a place to hang pirates and witches to a place for public speaking.
If you visit today, you may enjoy concerts and plays or an afternoon of relaxing things to do in Boston away from the hustle and bustle of city life.
4. Granary Burying Ground
If you fancy an afternoon searching for headstones among your list of things to do in Boston, you’ll find many notable Americans laid to rest at the Granary: John Hancock, Benjamin Franklin’s parents, Paul Revere, Samuel Adams, and Peter Faneuil (to name a few).
While there are only 2,345 headstones, it is estimated that approximately 5,000 people are buried in the Granary Burying Grounds—over 400 children are buried in the Infant’s Tomb alone.
5. King’s Chapel Burying Ground
For a period of time, the King’s Chapel Burying Ground was the only cemetery in Boston. You will find the first governor or Massachusetts, John Winthrop, buried here as well as Mary Chilton, the first woman to step off the Mayflower.
6. Boston Latin School Site
One of the most famous students at America’s first public school for boys was Benjamin Franklin. A mosaic marks the spot where the school first stood. Boston Latin School still operates today in the Fenway neighborhood of Boston.
7. Benjamin Franklin Statue
The statue of Benjamin Franklin was added as the first public portrait statue in Boston in 1856. It stands today outside the Old City Hall. Add this to your list of things to do in Boston.
It was placed on the 150th anniversary of Benjamin Franklin’s birth.
Franklin was considered to be a leader as a political thinker, statesman, and diplomat; he filled many roles as a writer, printer and publisher, scientist and inventor.
Of note, Benjamin Franklin was the only person to sign all four of the revolutionary-era documents that paved the way for our democratic nation today:
- Declaration of Independence
- Constitution of the United States
- Treaty of Alliance with France
- Treaty of Peace with Great Britain
8. Old Corner Bookstore
Though it stands today as a place of commerce, the Old Corner Bookstore, was built in 1718. It has been occupied as a residence, apothecary, pizza parlor, tailor shop, and publishing house where works such as Walden, Uncle Tom’s Cabin, and Battle Hymn of the Republic were first released.
As a historical site, it is obviously a bustling place to visit if you are looking for more things to do in Boston.
9. Old South Meeting House
Historically significant, the Old South Meeting House was saved from destruction in 1876. The Boston Tea party revolution began here as well as protests over the Boston Massacre.
10. Old State House
If you know United States History, you know that Boston patriots such as Samuel Adams and John Hancock spirited the idea of self-government. They opposed the rule of the British colonial power which found its seat in the Old State House, built in 1713. These patriots ignited the spirit of an independent nation.
Most significantly, the Declaration of Independence was first read from the Old State House’s balcony.
11. Boston Massacre Site
In the incident known as the Boston Massacre in 1770, British forces opened fire on angry protestors who threw snowballs, rocks and harsh words directly at the soldiers outside the Old State House. Five Bostonians were killed.
A stop at Faneuil Hall would fit well here on your Freedom Trail tour as you plan your day or days of things to do in Boston.
12. Paul Revere House
The Paul Revere House is a museum today and stands as the only home on the historic Freedom Trail. It has been preserved as the oldest structure in downtown Boston.
As you walk through the house, you get a glimpse into the life of residents in the 17th and 18th centuries.
13. Old North Church
You may have heard the famous phrase, “One if by land, two if by sea” in reference to the secret signal Paul Revere devised.
One lantern in the window of the Old North Church meant the British troops were taking the longer route by land and two lanterns meant the troops were advancing on the shorter route via the water.
At the time, the Old North Church was the tallest building in Boston with a steeple that was visible from far away in many directions. As well, the custodian of the church was a fellow patriot who had access to the church in the middle of the night.
The church has many other unique features beyond being famous for the TWO lanterns that hung in the steeple on the historic night of April 18, 1775. It is worth your time to visit if you are looking for things to do in Boston on your next trip.
14. USS Constitution
“Old Ironsides” as she became known during the war of 1812 is still a commissioned United States Navy warship today.
You can tour the ship as it is open to the public for on-board visits but be mindful that all guests 18 and over must have a driver’s license or passport to board the ship.
Let’s just say that it would have been more advantageous to be a Lieutenant or Captain rather than a regular enlisted man. Sleeping conditions differed dramatically from hammocks, to small rooms, to the spacious Captain’s quarters complete with his own cook. More advantageous indeed.
15. USS Constitution Museum
Once you finish touring “Old Ironsides”, don’t forget to add a stop at the USS Constitution Museum to your list of things to do in Boston.
The museum is interactive and hands-on. It was perfect for my girls when they were elementary aged.
After disembarking, our family travel adventures in Boston included a tour of the museum which had a lot of areas specifically designed for kids. The hammocks here were a big hit with even the biggest “kid” in our family.
16. Bunker Hill Monument
The Battle of Bunker Hill on June 17, 1775 immortalized the determination and fortitude of the colonial forces that were hardly equipped to face the power of the British Army.
A granite obelisk stands at a height of 221 feet to recognize the site of the first major battle of the American Revolution.
Climbing the monument is one of the things to do in Boston while you are there. After you have climbed the 294 steps of the spiral staircase to the top of the monument, the view from the observation deck overlooks Charlestown and Boston.
There is no elevator in the monument. So you will need to ascertain if you can safely ascend and descend the stairs of the monument.
Wander on over to the Bunker Hill Museum to learn more about the monument as well as the battle.
And there you have some significant sites along the Freedom Trail. These sites are some of the most memorable and historically significant things to do in Boston.
If you are interested there is a Freedom Trail Boston Guide App available.
Day Trips and Places to Visit in New England
17. Beacon Hill
If you are a photographer at heart, you might enjoy wandering some of the streets in Beacon Hill. It is one of Boston’s most picturesque neighborhoods. You’ll find steep, narrow streets lined with brick row homes.
Beacon Hill is considered to be one of the most expensive and desirable residential areas in Boston.
Take a walk down Acorn Street, a cobblestone avenue that simply oozes history. It has long been considered one of the most photographed streets in all of America. It is a must-see street when in Boston.
Our family travel adventures had us walking all over Beacon Hill—up and down cool streets with lovely architecture.
I happened to overhear my husband telling our girls as I caught up after taking pictures, “If your mom wants to take pictures, we will wait for her.” Love him.
18. The Charles River
After all of the walking and sightseeing, no doubt you and your kids are ready for a little break. Relax alongside the Charles River which flows 80 miles from Hopkinton, Massachusetts to Boston Harbor.
If the weather is nice, find a nice spot along the grassy Esplanade and watch kids playing in the park, enjoy the look of Boston in the fall, and simply people watch.
You’ll have fun seeing the watercraft along The Charles River. The river is often busy with boats, kayaks, canoes and sculls.
19. Public Garden
In the heart of Boston is a large park adjacent to Boston Common—Public Garden—the first botanical garden in America. Our girls loved the magnificent statue of George Washington, the brilliant colors of Fall foliage, and the “Make Way for the Ducklings” statues.
If you are planning a trip to Boston with your children, be sure to take into consideration some of the fun things to do in Boston that they would enjoy.
20. Legal Seafood
While not an historical part of the things to do in Boston, it is one of the fun and delicious places to eat. Our girls loved the seafood dishes, the view, and walking along Long Wharf.
21. Harvard
On our third day in Boston, the sun began to shine. We still needed our jackets for some of the day, but it was nice to bid farewell to the rain. That’s Boston in the fall folks!
We stopped at Harvard in Cambridge (about a 20 minutes drive from Boston) and my youngest was quick to spy the World’s Only Curious George Shop. While it closed in 2021, it was fun to wander through the store back then.
Before we walked across campus, our older two girls spied the Harvard Coop (not co-op. Coop as in chicken coop). We had to make a quick stop and check out the official apparel of Harvard.
We walked across campus. It was a Saturday morning, so the campus was pretty quiet.
Harvard is pretty iconic so I would add it to your must-see list of things to do in Boston just to say you’ve been there.
22. Little Italy and Mike’s pastry
Walk through Boston’s Little Italy and you’ll surely find Mike’s Pastry in Boston’s historic North End on Hanover Street. Or at least the line to get into the shop.
Jump on the end of the line if you fancy some amazing cannoli, biscotti, or gelato. If you are close to the Paul Revere House, Mike’s Pastry is a short one-minute walk.
Not only is the cannoli delicious, but visiting Mike’s is also a Boston tradition. Be sure to add it to your list of things to do in Boston!
23. Plimoth Plantation and Plimoth Patuxet Museums
One hour outside of Boston is Plymouth, Massachusetts where you can experience the history of Plymouth Colony and the Indigenous homeland. It is one of the places to visit in New England that you shouldn’t miss either.
Major exhibits on the plantation include the Patuxet Homesite, the Mayflower II, a 17th-Century English Village, and the Plimoth Grist Mill.
Start with an orientation movie about Wampanoag (pronounced Wam-pan-og) people and the people of the 17th Century English Village. From there, you can wander through the outdoor living exhibits.
When we visited, the Wampanoag people were not “in character” since they would have then spoken in their native tongue and we wouldn’t have been able to converse with them, but they talked about the life of the family living here long ago. While visiting, they cooked over their fires, wove handbags, and prepared to burn out a tree to make a canoe.
Proceed onto the English Village where actors are in character.
Chris was asked at one point where he lived, and the person responded, “I know not of this Colorado that you speak of.”
Our young girls (at the time) enjoyed the Craft Center where they learned more about how skilled craftspeople recreate the world of the 17th century.
The Mayflower II, a full-size re-creation of the original ship was closed when we visited, but it is now available for tours at the State Pier in Pilgrim Memorial State Park. It has been fully restored.
24. Day Trip to Cape Cod from Boston
I imagine you could spend an entire weekend just exploring Cape Cod, the Atlantic Coast, and the surrounding area if you weren’t looking initially for things to do in Boston.
Cape Cod, characterized by its hook-shaped peninsula, is also known for windswept beaches, lighthouses, quaint inns, and great food. Whether you have a day or more to explore, you’ll love your time in Cape Cod.
Pack a picnic lunch and enjoy lovely drives through stately neighborhoods, visits to a number of beaches, including Sea Street Beach and Howes Street Beach, and lighthouse explorations.
25. Dunkin’ Donuts
This would probably be #1 if my girls were ordering this list of things to do in Boston. They didn’t grow up in locations where you could find Dunkin’ Donuts on almost every street corner. It was a must stop for them.
NOTE to parents * This stop won’t be FREE!
Gear for Visiting Boston in the Fall
Boston in the fall is the perfect destination for a Fall Break weekend. Boston is full of history, good food, and brilliantly colorful trees.
If you are a photographer, pack your camera and lenses and be prepared for the picturesque moments. Wondering what to bring? Check out my favorite photography gadgets.
Frequently Asked Questions
How long does it take to walk the whole Freedom Trail?
You can walk the Freedom Trail in about 90 minutes to 2 hours. If you plan to stop and explore along the way, plan to spend the whole day.
Where does the Freedom Trail start?
The start of the Freedom Trail is Boston Common.
Where does the Freedom Trail end?
The Freedom Trail ends at the USS Constitution Museum.
What beach on Cape Cod has the softest sand?
Old Silver Beach, famous for its fine sand and crystal clear water, is the perfect beach for families.
How far is Boston from Cape Cod?
It is only about 70 miles which makes it great for an easy weekend getaway or even a day trip. Either way, it is one of the best places to visit in New England.
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Final Thoughts on 25 Seriously Cool Things to Do in Boston, Massachusetts in the Fall
History comes alive in Boston along The Freedom Trail.
If you are looking for a destination for Fall Break that is full of history, you can never go wrong planning things to do in Boston as well as discovering places to visit in New England.
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What an amazing list. We love Boston. The children’s museum was our favorite.
I love Boston! Mikes pastries was my favorite.
We had such a great weekend, even in the rain. And Mike’s Pastries was just a great bonus.
So many interesting spots! Beacon Hill looks stunning!
Stunning areas with some impressive history as well.
Boston has so much to offer! I love Mike’s – there is one in Harvard Square, as well, which is convenient for us Harvard students. 🙂 The Plimoth Plantation sounds awesome, I need to check it out.
I didn’t know about the one in Harvard Square. Handy for the students for sure.
Ditto. My husband and I are both homesick for travel.
It has been a while since I have been to Boston. I didn’t get to see much when I was there but would love to make a return trip. Such great history in Boston.
Boston is a place where history really comes alive for kids.
Awesome list! Boston’s one of the places in the country I’ve never visited, but plan to one day! I’ll bookmark your post.
Thanks. I think you will love it when you get there.
Such a helpful article! Would love to go to Boston one day. thank you so much for sharing!
Then I have done my job!
Visiting Boston in the Fall has been on my bucket list for so long! Thanks for highlighting so many things to check out too. I’d love to do the Freedom Trail and many of the historical sites, and Beacon Hill looks stunning
I think you will definitely enjoy visiting Boston. The Freedom Trail is pretty amazing.
Great post! I really appreciate all the historical facts and research that were woven into the post. I am actually visiting Boston in a few weeks, and I was super pleased to discover that 90% of these spots are already on my itinerary! I can’t wait 🙂
You should have an awesome time and lots of photo opportunities.
I went to Boston 2 summers ago and I walked the Freedom Trail. Next time I go, I want to check out Harvard. This is a great list!
Thanks, we went in the Fall and absolutely loved the colors along the way.
I love Boston! I have visited this amazing city many years ago and have fond memories. So many historical places, scenic views and yummy food too. Lovely photographs! 🙂
Thanks! Boston is full of history. I think it made some subjects in school come more alive for my girls after we visited.
Cape Cod looks beautiful – definitely looks like something that would be on my list if I ever find myself in Boston!
I hope you make it someday. I would love to return and explore some more. Even though it was almost ten years that we took our daughters, they still talk about it as being one of their favorites.
What a cool list! I’ve wanted to go to Boston for quite some time. There is so much history and things to do. And the Freedom Trail looks like a great way to see some of the sites!
I highly recommend the Freedom Trail. You won’t be disappointed.
Gorgeous photos and Boston is a place I have always wanted to visit…thanks for the to DO list it will help
Very cool post! Super informative. I’ll have to check out Boston sometime. Thanks for sharing!
Boston is on my list of states to visit. I will be using this as one of my travel guides. Thanks for sharing.
Great guide! I lived in Boston for a few years, wonderful city!
Ok, as a native Bostonian- I approve this post!!! well done! You should check out the Boston Tea Party Ship and Museum- super fun! And leave time to head north to Salem and Gloucester!
I have not one but two friends who are in Boston! I’ve been dying to go for so long, so much to do and see.
So many interesting spots! I’d love to sample Mikes pastries. Thanks for sharing!
I absolutely love this list. It somehow felt a bit less touristy, and I love that. The history in Boston is incredible and I need to go with the family and check out these places. The last time we were in Massachusetts we focused on Cape Cod.
I went to Boston in December a few years ago and it was all dead, yet I fell in love with the city. I can only imagine how beautiful it would be during autumn!!! Saving this
My husband and I need a proper Boston trip! Thank you for all this amazing inspo. We planned a couple days in Boston, returning from the Caribbean one year on the way back home and encountered REALLY bad weather (and didn’t have the right clothes, either). We made the best of it, but definitely need to go back and see all the things we missed out on. Thanks for all these great tips!
Great advice! Boston and Massachusetts are very nice in the fall. If I had to add anything, I’d probably suggest climbing Blue Hill, if time permits.
There’s so much to do in Boston! I love the city and starting out a visit with the Freedom trail is acutally the best way to get to know the city and its history.
So many great things to do in Boston! What a lovely city to visit.
There’s so much history in Boston, I’d love to visit. (Of course, the great accent is another draw!) The Freedom Trail looks interesting.
We had one amazing fall day in Boston a few years ago on a cruise. Hoping to make it back there for some of these fun things. The top of my list is visiting Louisa May Alcott’s home & Kennedy Library.
This list is perfect! I am planning to spend more time in Boston and will use this to help with planning.