Boston In One Day: The Perfect Freedom Trail Itinerary (2024)
Want to know how to see Boston in one day? We’ve got you covered with this perfect freedom trail itinerary!
We spent a day exploring Boston as part of a larger road trip around the US.
At this point, we had just made our way up the East Coast from places like Savannah, Charleston, Williamsburg, Washington DC, Philadelphia, New York, and Newport.
From Boston, we were continuing our road trip through Cape Cod and then starting our trip back West through the Poconos, Ohio, and Branson.
This trip was JP’s first time visiting Boston, but I had been previously on a high school history class trip over a week-long spring break.
It was fun to experience the city in a new way and to create our own itinerary for exploring in just one day.
You can watch our full experience exploring Boston on our YouTube Channel.
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Things To Do In Boston In One Day
What I love about the way the tourist experience is designed in Boston is that you just follow the red bricks.
They will take you everywhere you need to go along the Freedom Trail, which highlights all of Boston’s must-do’s.
We recommend parking in the underground garage near the USS Constitution for $22 for the day.
It is cheaper than being in the middle of town and situates you perfectly along the freedom trail.
Click Here To Download Your Self-Guided Audio Walking Tour Of The Boston Freedom Trail Today!
1. Bunker Hill Monument
This is where the Boston Freedom Trail begins.
The Bunker Hill Monument, a soaring 221-foot granite obelisk, stands proudly atop Breed’s Hill in Charlestown, Boston.
This structure holds significance as it commemorates the Battle of Bunker Hill, a pivotal event during the American Revolutionary War.
The battle, fought on June 17, 1775, was one of the early clashes between the American colonists and British forces.
Today, the Bunker Hill Monument stands as a testament to the bravery and sacrifice of those who fought for independence.
You can climb the monument’s 294 steps to reach the top and be rewarded with panoramic views of Boston’s skyline and the surrounding areas.
2. USS Constitution
The next stop on the Boston Freedom Trail is the USS Constitution.
This was a little bit of a walk, but it was through a really nice neighborhood.
After crossing the bridge over to Boston’s North End, each stop of the Freedom Trail is much closer together.
Launched in 1797, she is the oldest commissioned warship afloat in the world.
The USS Constitution played a crucial role in the War of 1812, earning her the nickname “Old Ironsides”.
Today, it is docked at the Charlestown Navy Yard, where you can step aboard and explore this piece of history.
The ship also houses a museum.
It showcases artifacts, memorabilia, and interactive exhibits, providing deeper insights into the life of sailors during the early 19th century.
3. Copp’s Hill Burying Ground
From the USS Constitution, this was about a 20 minute walk.
Parts of the walk took longer since we had to wait at a few crosswalks.
This burying ground is Boston’s largest colonial burying ground.
It goes back to 1659 and is the burial site of most North End residents of the time.
4. Old North Church
The Old North Church is only about a minute’s walk up the street.
The Old North Church is a cherished icon of American history and an essential destination for visitors exploring the city.
Built in 1723, this Georgian-style church gained fame during the American Revolutionary War.
Its steeple served as a signal station during the night of April 18, 1775.
The legendary “One if by land, and two if by sea” lantern signal, displayed by Robert Newman and Captain John Pulling, alerted Paul Revere about the British troops’ movements, igniting the events that led to the famous “Midnight Ride.”
5. Paul Revere House
If you blink you’ll miss this one.
As you make your way through the North End you could almost walk right past it.
The only giveaway was that there were significantly more people gathered nearby than where we had just been walking.
As the oldest surviving structure in the city, this 17th-century home was once the residence of Paul Revere.
Visiting this well-preserved dwelling offers an opportunity to experience the daily life of an influential figure from the American Revolution.
The house showcases period furnishings, personal artifacts, and interactive exhibits.
It provides valuable insights into Revere’s remarkable life and his role in the events leading up to the American Revolution.
6. Faneuil Hall
This was about a 10 minute walk from Paul Revere’s House.
Faneuil Hall is a historic marketplace that holds a special place in America’s revolutionary heritage.
Built in 1742, this building has served as a meeting place, marketplace, and a symbol of free speech for centuries.
Often referred to as the “Cradle of Liberty,” Faneuil Hall was a venue for impassioned speeches by famous patriots such as Samuel Adams and others who rallied the colonists to seek independence from British rule.
Today, the Faneuil Hall Marketplace is a bustling hub of activity, featuring an array of shops, restaurants, and street performers.
A fun surprise was a massive Christmas store we found.
We always pick up a Christmas ornament as our souvenir wherever we visit, so we knew that’s where this one was coming from.
Check out the Youtube video at the top of this post to see the inside!
7. Quincy Market
Quincy Market is a historic marketplace.
Built in 1826, this architectural gem is named after the city’s namesake, Mayor Josiah Quincy.
Quincy Market is a food lover’s paradise, offering an array of dining options from local specialties to international cuisines.
You can enjoy everything from clam chowder and lobster rolls to gourmet sandwiches and street food.
The market also features numerous boutiques, artisanal shops, and entertaining street performances.
8. Boston Massacre
Just across the street is the Boston Massacre Site.
The Boston Massacre Site is an essential historical landmark that holds significance of America’s struggle for independence.
This is the site where a tragic event unfolded on March 5, 1770.
Tensions between British soldiers and the colonists escalated, resulting in a deadly confrontation that left five civilians dead.
The incident served as a catalyst for further unrest and solidifying the colonists’ resolve to break free from British rule.
The site is commemorated with plaques, offering historical context and honoring the lives lost in the pursuit of liberty.
9. Old South Meeting House
The Old South Meeting House holds a place of prominence in American history.
It was built in 1729 as a Puritan place of worship.
This Georgian-style building gained fame during the Revolutionary era for its role that led to the Boston Tea Party.
It was here, on December 16, 1773, that a gathering of colonists convened to protest the Tea Act.
The impassioned debate ultimately sparked when the Sons of Liberty, disguised as Mohawk Indians, dumped British tea into Boston Harbor.
The museum inside the building houses exhibits, artifacts, and multimedia presentations that vividly narrate the events of the past.
10. Old City Hall
The Old City Hall is a historic landmark that holds both architectural and civic significance.
Completed in 1865, this magnificent structure served as Boston’s City Hall until 1969 when the current City Hall was established.
The building showcases a blend of Second Empire and Renaissance Revival architectural styles.
It boasts a distinctive clock tower and a grand façade adorned with intricate details.
The Old City Hall represents a pivotal period in Boston’s history when the city was growing into a bustling metropolis.
Today, you can step inside and appreciate the preserved interior, including the former council chambers and elegant staircases.
The building now houses the Bostonian Society’s museum, where exhibitions and artifacts illuminate the city’s history and role in shaping the nation.
11. Granary Burying Ground
The Granary Burying Ground, nestled in the heart of downtown Boston, is a beautiful cemetery steeped in history.
Established in 1660, this is one of the city’s oldest burying grounds and serves as the final resting place for several notable figures from American history.
Among the approximately 2,300 gravestones lie the tombs of prominent figures such as John Hancock, Samuel Adams, Paul Revere, and other key contributors to the American Revolution.
The gravestones themselves serve as fascinating historical artifacts, with intricate carvings and epitaphs that offer glimpses into the lives of those buried there.
12. Boston Common
After another 5 minute walk, we made it to the end of the Boston Freedom Trail!
We spent quite a bit of time walking around here.
Boston Common, the oldest public park in the United States, is a cherished historic landmark and a must-visit destination for travelers exploring Boston.
Established in 1634, this sprawling green oasis has played a central role in the city’s history and continues to be a beloved gathering place for locals and tourists alike.
As a site where countless events, protests, and celebrations have taken place throughout the centuries, Boston Common is steeped in rich historical significance.
The park’s pathways, ponds, and lawns provide a peaceful respite from the bustling city, making it a perfect spot for a leisurely stroll, a relaxing picnic, or some quiet contemplation.
We saw the Make Way For Ducklings statues (I bought the book and still have it from my high school trip).
We also saw the Good Will Hunting bench.
13. Massachusetts State House
Just across the street is the Massachusetts State House.
The Massachusetts State House, perched atop Beacon Hill, is a magnificent and historically significant landmark that should not be missed during a one-day exploration of Boston.
Completed in 1798, this neoclassical-style building serves as the seat of the Massachusetts government and houses both the state legislature and the governor’s offices.
The State House is famous for its gleaming golden dome.
It was originally made of wood and later covered in copper and then gilded with gold leaf.
A guided tour of the State House takes you through the Hall of Flags, the Senate and House of Representatives chambers, and other historically significant rooms adorned with exquisite artwork and artifacts.
14. Fenway Park
Jumping ahead in our itinerary a little since we’ll cover meals and snacks later, after dinner we walked back to our car which was still parked in the garage back by the USS Constitution.
It was maybe a 20 minute walk or so.
We just followed the Freedom Trail bricks back since it’s the easiest way to navigate around Boston.
From there, we decided to do a little extra sightseeing.
We drove by Fenway Park and around Harvard.
By the time we reached Harvard it was dark, so we don’t have any photos.
After that we drove back to our resort in Falmouth, which was about an hour and a half drive.
Where To Eat In Boston In One Day
Boston has a great mix of the iconic New England cuisine, historic taverns, and some of the best Italian food you’ll find in the world.
It’s really hard to pick just a couple to eat if you’re only here for one day.
✅ Mike’s Pastry
Back in the North End we had picked up a Boston Cream Pie and a Nutella Cannoli from the famous Mike’s Pastry shop.
We ate the Boston Cream Pie right away, but saved the Nutella Cannoli and ate it while we were at Faneuil Hall and Quincy Market.
✅ Cheers
Down by Boston Common is the Cheers pub.
The inside of this one doesn’t actually look anything like the show, but I hear there is a Cheers pub replica somewhere in town that is made to look like the set.
✅ Trattoria il Panino – North End
Even though we were all about eating all the New England style food while we were up there, we just couldn’t pass up Italian food in the North End because pasta is my favorite.
I could eat pasta for every meal and never get tired of it.
There were so many places to choose from, but this was America’s original Trattoria and I was craving a carbonara pasta, so this is where we ultimately decided to have dinner.
They had part of the street closed off for additional outdoor dining, so we didn’t have to wait long for a table.
I had the Spaghetti Carbonara and JP had the Lobster Ravioli.
We ended up taking about half of my pasta back as leftovers, so we didn’t get dessert since we were too full.
I highly recommend this place if you’re looking for good Italian food in Boston!
✅ Warren Tavern – Charlestown
From our parking garage, Warren Tavern was about a 10-15 minute walk.
But it’s very scenic and it was our first thing we did in Boston, so we enjoyed it.
Warren Tavern’s claim to fame is that it is the oldest tavern in Massachusetts, having been established in 1780.
George Washington and Paul Revere were both known to be frequent visitors!
We were definitely treating ourselves today since we knew Boston would be one of the biggest highlights of the trip.
So we started with drinks since we knew we wouldn’t be driving at all the rest of the day.
JP got the Sam Adams Summer Ale since that’s what’s local to the area and I got the Down East Original GF Cider since that is the local cider to the area.
As an appetizer, we shared Steak + Cheese Eggrolls which we have noticed are popping up on menus more often (and we’re not mad!).
We also shared a cup of New England Clam Chowder since it’s a local specialty.
For lunch we shared the Shepard’s Pie since that is always one of our all time faves.
We were too full for dessert, but we knew we would be snacking throughout the day, so we weren’t too bummed.
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Conclusion: Things To Do In Boston In One Day
Exploring Boston in one day is quite a feat, but with the help of the Boston Freedom Trail, you’ll see all the must-do’s and you won’t ever get lost!
