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 draws our family to our chosen destinations. Hmmmm, or maybe that’s just me and my husband is just awesome enough to oblige.
Things to Do in Boston
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Boston is the perfect destination for a Fall Break weekend that is full of history, good food, and colorful trees.
In fact, we invested in gloves and umbrellas once arriving in Boston 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.
Our first stop? 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 fun 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 historical 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.
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 the Freedom Trail Official Online Brochure for a self-guided tour along the trail.
Put on your walking shoes [affiliate] and step back in time.
The official beginning of the Freedom Trail is 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.
These are a few of the sites along the trail that we visited from our research for things to do in Boston on our girls’ Fall Break.
Boston Common is American’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 calm things to do in Boston away from the hustle and bustle of city life.
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.
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.
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.
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 as 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: The Declaration of Independence, the Constitution of the United States, the Treaty of Alliance with France, and the Treaty of Peace with Great Britain.
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.
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.
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.
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.
Faneuil Hall would fit well here into your Freedom Trail tour as you plan your day or days of things to do in Boston.
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.
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.
“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.
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, we toured 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.
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 Other Fun and Notable Things to Do In Boston and the Surrounding Area
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 walked 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.
The Charles River
After all of the walking and sightseeing, no doubt you 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 or simply people watch.
You’l have fun seeing the watercraft along The Charles River. The river is often busy with boats, kayaks, canoes and sculls.
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.
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.
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.
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 earlier 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-do list of things to do in Boston just to say you’ve been there.
Little Italy – 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!
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.
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, is now available for tours at the State Pier in Pilgrim Memorial State Park. It has been fully restored.
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.
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Final Thoughts on The Best Things to Do in Boston, Mass
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 searching for things to do in Boston and the surrounding areas in Massachusetts.