17 Riveting Historic Sites in Boston

17 Riveting Historic Sites in Boston

Historic Sites in Boston

Welcome! Join us as we explore all of the amazing historic sites in Boston!

Boston is the 4th stop along our American History road trip. We drove from NYC to Boston along the coast, through Connecticut and Rhode Island. We saw beautiful coastline and our first light houses. I kept wishing we had scheduled more time through that area to stop and explore.

One of the things I really love about homeschooling is the flexibility to travel and learn on the road. I love that we are not beholden to anyone else’s schedule. As long as my husband can get work off, we can go. We love to visit places during their off-season, when they are empty and there are no lines to wait in, because all the other kids are in school.  We also tend to save money that way. Just be sure to check schedules and make sure the things you want to see are open!

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Sites in Boston

Boston is probably my very favorite city in the entire world.  I just love the juxtaposition of the historic and the modern — the charming cobblestone streets that Paul Revere walked on butted up against the modern paving materials and high rise office buildings. I love that all of the sites in Boston are safe, kid-friendly and walkable. Most of the educational activities geared toward kids are fun for adults, too.

I love that the subway is old and a little decrepit in places (though quite clean and nice!) and that the inner-city-trains all have big rotating sections in them so they can turn, because they’re a mostly modern addition to an old city. I love the skyline and the coast and the waterways. I love the charming European architecture in Back Bay and how all the hills require sloped steps and doorways. It all blends into absolute perfection!

The historic sites in Boston are the perfect way for families to explore our nation’s history and have a great time together along the way

We spent 3 days in Boston and one in Lexington/Concord, just an hour outside of Boston.


Boston Freedom Trail

The Boston freedom trail is a 2.5 mile path through Boston that takes visitors to 16 18th and 19th-century historical sites important to the American Revolution. The city of Boston has installed red bricks, and painted a red line where bricks weren’t possible, for visitors to follow.

It honestly is so easy to find your way!

You can join a guided tour, hosted by actors in eighteenth-century costumes, to walk the Freedom Trail and see all the sites in Boston. They will tell you stories and history and teach you about the American Revolution. The walking tour (reg. $14) is included with your purchase of a Go Boston card.

However, we always prefer to walk the trail at our own pace so we can stop and play wherever we want to. Also, the hubs is a history buff and can answer even the most outrageous questions, plus we’ve studied the American Revolution extensively in our homeschool.

Along the way, we used this freedom trail app, brochures, and books we bought to learn more about the people and the Revolutionary War events. The app highlights the rich history of the American Revolution as it unfolded in Boston, as well as a wide assortment of historic sites just steps off the Trail.

If you are worried about your little people (or yourself!) walking the whole way, you can buy a hop-on/hop-off Boston trolley sightseeing ticket that will deliver you between the sites along the freedom trail. Admission (reg. $42) is included with the purchase of a Go Boston Card.

>>>Go Boston Card: save up to 15% instantly on 3, 5 and 7 day cards!<<<

We exhausted our children and ourselves by walking the entirety of Boston’s Freedom Trail our first day in Boston. Be sure to wear good walking shoes and take plenty of water and snacks.

Several of the sites along the way require admission and offer a tour, but some are just walk-through or maybe peek-inside-then-continue-on-your-way type sites. Admission to the sites that charge admission is included with your purchase of a Go Boston Card , which is a fantastic deal.

All of the historic sites in Boston are within a couple of miles of each other and, though tiring, completely doable in a day. We stopped for a picnic mid-tour and finished before dinner time, with 7 kids and a very pregnant mama.

1. Boston Commons-  Here we are walking across the commons (where the colonists used to graze their livestock) toward the State House

2. Massachusetts State House

3. Park Street Church – sitting on the steps

Boston Freedom Trail. American History tour road trip for families with kids

4. Granary Burying Ground (find the grave of Mary “Mother” Goose)

5. King Street Chapel

Boston Freedom Trail. American History tour road trip for families with kids

6. Ben Franklin Statue and Boston Latin School 

Boston Freedom Trail. American History tour road trip for families with kids

7. The Old Corner Bookstore

8. The Old South Meeting House. My favorite of all of the historic sites in Boston, this is where Samuel Adams and 6000 colonists met and voted to to put a guard of 25 men on the tea ship Dartmouth to ensure that the tea would not be landed. Over the next several weeks, colonists and political leaders argued back and forth about the issues surrounding the tea, but no resolution could be reached. December 16, 1773, the colonists met the final time. As with previous meetings, all attempts at diplomatic negotiations with government officials had failed. The Patriots had exhausted all legal means to keep the tea from being unloaded. Hearing the news, Samuel Adams declared: “This meeting can do nothing more to save the country!” as a pre-arranged signal to the Sons of Liberty to don their disguised, march down Milk Street, adjacent to the meeting house, and board the Dartmouth in the harbor. The Boston Tea Party ensued. Admission (reg. $6) is included with the purchase of a Go Boston card.     

  >>> Go Boston Card: 50+ Boston attractions, tours and museums for one low price. Save up to 55% on tickets!<<<

9. The Old Statehouse- When the Declaration of Independence was first read in the square outside the Old State House, the colonists got up on the roof and tore down the lion and the unicorn, symbols of the British monarchy. March 5, 1770, the Boston Massacre happened on the circle where Kendel is standing with the stroller. The Old Statehouse has amazing exhibits, including a sextant, which is a navigation tool (used by Nat Bowditch!) for sailors, colonial charters, colonial art and a large diorama of Boston during colonial times. You’ll want to tour this place. Admission (reg. $10) is included with the purchase of a Go Boston card.

10. Faneuil Hall. The kids earned a Junior Ranger Badge by filling out the Downtown Boston Junior Ranger Activity Book. This booklet asked questions about the sites we had seen on our walk and reinforced what life was like during the time period. Quincy Market, right out Faneuil Hall’s back doors, is a fun place to grab a quick snack or souvenir.

11. Paul Revere’s house. The oldest home in Boston’s Historic North End, will make you feel like you stepped through a time warp. It’s another favorite historic site in Boston. Paul Revere fathered 16 children by 2 different wives. You will be amazed at how small the house is for the large family of a very renowned man. You’ll love the immense fireplace, built for cooking in, and the narrow staircase. Admission (reg. $5) is included with the purchase of a Go Boston card.                                                                                                                                                             Paul Revere's House. Freedom Trail. American History tour road trip for families with kids.

12. Copp’s Hill Burying Ground

13. The Old North church. This site in Boston has one of the lanterns (One if by land, two if by sea) and the other is at the Concord Museum.

Old North Church. Freedom Trail. American History tour road trip for families with kids.

14. Old Ironsides aka USS Constitution. We loved this historic site in Boston, too! It has a fascinating tour. You’ll see how the sailors used to sleep, in hammocks, and where and how they ate and how the canons and sails worked. You’ll see captain’s quarters.


15. Bunker Hill Monument. After walking the Freedom Trail all day, seeing all the historic sites in Boston, I didn’t particularly want to climb all the stairs to the top of the Bunker Hill Monument, but my kids did. They ran the whole way! There is a fun park around the monument, and a museum across the street with some neat exhibits.

I love the architecture of the older homes in that area, too. I heartily recommend forgoing some of the trolley rides and just spending some time walking through the neighborhoods!


A few more sites in Boston:


The Boston Swan Boats

The Boston Swan Boats are among the most iconic figures in the city. Made famous in stories like Make Way for Ducklings and The Trumpet of the Swan, the Swan Boats are the only vessels of their kind in the world.

The pond and the boats are found in Boston’s extensive public gardens, which many Bostonians consider their favorite part of the city. You can soak up the beauty of the surrounding gardens as you enjoy riding the swan boats. It’s a great place for a picnic, too!

Admission (reg. $3.50) is included with the purchase of a Go Boston card.



Prudential Center Skywalk Observatory

With its 360-degree views of downtown Boston, the Skywalk Observatory atop the Prudential Center is located 50 stories up in the air. You’ll find several interactive exhibits and historical displays located throughout the Observatory, so you’ll learn about the buildings you’re seeing below and become acquainted with the layout of the city.

Admission (reg. $19) is included with the purchase of a Go Boston card.


Fenway Park

Whether you are a baseball fan or not, you won’t want to miss this classic Boston experience at “America’s Most Beloved Ballpark”. Fenway Park is more than an iconic baseball stadium; many Bostonians consider it the heart and soul of the city.

Explore the park where Babe Ruth pitched, Ted Williams hit, and Carl Yastrzemski led his amazing career. Visit Pesky’s Pole and sit atop the world famous Green Monster overlooking left field.

Entertaining and knowledgeable guides provide entertaining commentary, stories, and trivia as they take visitors through areas not typically seen by the general public. You’ll see all of Fenway Park’s infamous features, including Duffy’s Cliff, Pesky’s Pole, Williamsburg, The Triangle, and the Lone Red Seat. Admission (reg. $20) is included with the purchase of a Go Boston card.



New England Aquarium Whale Watch

Want to see the really big animals? The New England Aquarium partners with Boston Harbor Cruises to give visitors front row seats to view the ocean’s most fascinating and magnificent animals. New England Aquarium Whale Watches conveniently leave from Central Wharf.

This cruise will take you out into the Atlantic Ocean to the Stellwagen Bank Marine Sanctuary, a rich feeding ground for whales, dolphins, sea birds, and other marine life. Learn all about these fascinating marine mammals from onboard naturalists trained by Aquarium experts. Creatures you might see are: humpback whales, finback whales, minke whales, white sided dolphins, and more.

Please make your reservations in advance. Arrive at least 30 minutes before your cruise time; the cruise will take approximately four hours.

Admission (reg. $27.95) is included with the purchase of a Go Boston card.


Lexington and Concord

We arranged to be in Lexington on April 19th, the anniversary of the battle of Lexington, so we could see the re-enactment of William Dawes riding his horse across Old North Bridge calling men to arms, shouting “The regulars are coming!” The re-enactment took place at 6:30 in the morning and was very cold, but worthwhile. My kids were impressed with the firing of the canons and the uniforms, and particularly by the fact that William Dawes was being played by a girl!


Lexington Green

First, visit Lexington Green, the location of the ‘shot heard ’round the world’. Around the green are historic buildings, staffed by people who wear colonial costumes and play colonial characters. Each of them will tell you all about their place in Revolutionary history.

Buckman’s Tavern

You’ll see Buckman’s Tavern, a favorite gathering place for militiamen on days when they trained on the Lexington Green, and the Hancock-Clarke house, where John Hancock grew up. Admission (reg. $8) is included with the purchase of a Go Boston card.

Hancock House

The Hancock house was the destination of Paul Revere on the night of April 18, 1775, as he and William Dawes rode from Boston to warn the sleeping Samuel Adams and John Hancock of the coming of British troops. Lexington Visitor Center is also right there.



Minute Man National Historical Park

Next, visit Minute Man National Historical Park just a few minutes down the road. The visitor’s center has a truly fantastic presentation about early American History, so that when you walk the Battle Road you will understand the significance of the tavern and homes you pass, along with the lovely rock walls and topography.

Battle Road

Be sure to save some time to walk the Battle Road. There are so many historical sites along Battle Road that I can’t list them all, but you will find all of them just as interesting and worthwhile as the Freedom Trail sites in Boston.


Orchard House

Orchard House, along with it’s neighbor, The Wayside, is only a few more minutes down Massachusetts Avenue. I’ve never toured the Wayside, but I love the Orchard House tours. They tell you stories they tell about the family as you walk through the house. You’ll get to see May’s art studio and her bedroom, with her drawings on the walls and trim.

You’ll get to see Louisa’s bedroom, with the small writing desk her father made her. You’ll get to see the well right in the floor in the kitchen, considered an innovation at the time, and the actual large vessel sink Mrs. Alcott and the girls worked at. Louisa May Alcott has long been a beloved author in our home. Admission (reg. $10) is included with the purchase of a Go Boston card.

Orchard House; Concord, MA. American history tour road trip for families with kids
Orchard House, Concord, MA

After Orchard House are the Concord Museum and Emerson house, right across the street from one another. One of the lamps from the Old North Church (one if by land, two if by sea) is at the Concord Museum, along with myriad other interesting historical artifacts from famous local authors. Admission (reg. $10) is included with the purchase of a Go Boston card.

It’s remarkable to think of literary notables Louisa May Alcott, Ralph Waldo Emerson, Henry David Thoreau, and Nathaniel Hawthorne being neighbors and friends! Why did so many notable, early American authors hale from the same, small town?

You can see all of their graves at Sleepy Hollow Cemetery at 34 Bedford Rd. in Concord.

>>>Save up to 50% with a Go Boston Card!<<<


At the next intersection go north and park at the lot near the Old North Bridge. While fighting technically occurred first at Lexington Green, North Bridge is considered the site of the first battle of the Revolution because it was the first time that the militia was formally ordered to fire upon British troops. In doing so, they had committed treason against the empire. The Revolution had begun.

Old Manse and North Bridge

The Old Manse is located next to North Bridge. They always have a fantastic heirloom garden for visitors to learn from. Both Emerson and Hawthorne lived here at different times.



Walden Pond

While you’re out that way, be sure to stop at Walden Pond and see the tiny, primitive cabin that Thoreau lived in for a couple of years and wrote about. It’s a beautiful, good-sized lake (I expected a tiny pond…) with picturesque hikes around the perimeter. Stop at a drive-through in town and have a picnic at Walden Pond, or better yet, stop at a grocery store for your picnic.



You should also take a few minutes to drive through town and gawk at the beautifully simple colonial architecture. After visiting Concord/Lexington the first time, I tried and tried to find the hubs a job in the area so we could move there. Not only are the homes beautiful, but the landscape is beautiful and thickly wooded.

There is so much to see here you could happily spend  a couple of days.







The Best Ways to Save Money When Visiting the Sites in Boston

Food. We pack most of our own food. We try to reserve hotels with a free breakfast, but when we can’t we take milk and cereal, fruit and yogurt; stuff that doesn’t require cooking and isn’t messy. We generally eat lunch someplace fun, as it adds to the experience, but is usually cheaper than dinner.

I make freezer meals ahead of time to take with us for dinners, and we fill a cooler with lunchmeat and cheese for sandwiches and always fill a bin with snacks.  If we are traveling for more than a week, we will frequently stop at a local grocery store to replenish our supplies.

Lodging. I always check a few comparison sites, like Priceline, for deals. Kayak allows you to sign up for price alerts for particular hotels or dates you’re interested in, so when the price drops, you’ll get an immediate email notification. Also, multiple sites lists accommodations after late cancellations, allowing you to score the rooms for a reduced price.

Check out Roomer and Cancelon for deals. And finally, sometimes you can get a better deal just calling the hotel and booking directly with them.

Fun. Admission to attractions is typically where we spend the most money, since it’s always times nine people. We could have spent a small fortune in admissions, because we visited so many sites in Boston each day, but we were able to save a little over 50% by purchasing Go Boston cards.

>>>Get a FREE Boston Duck Tour ticket on all 3, 5 and 7 day Go Boston Cards<<< 

City Pass also has some great deals, but for us the Go card was a better deal for us this time, since they included several of the places we visited in Lexington and Concord. I also liked that we were able to skip the line at several places.

With the app, you don’t even need to get tickets at the Prudential skywalk — you can go straight to the 50th floor. I loved that downloading the Go app on my phone allowed me to not have to keep track of anything. Each attraction could scan ALL of our tickets on my phone.


The only way to get the very best deal for your own family is to plan out exactly which sites in Boston you want to see, then check out both discount passes and see which one will give you the biggest discount.

Also, be sure to check the ages on the passes. We didn’t need tickets at all for my 2 yr old, and my two oldest kids were considered adults and needed an adult pass.

Some of the attractions are only included with certain passes, too. The 3-day all-inclusive pass was the best deal for my family, because we wanted to see and do everything, but they have build-your-own passes for those who are visiting for a shorter time or only want to visit a few attractions.

Just make sure you do a little research and planning so you can get the most bang for your buck.

Transportation. You don’t want to drive in the city. You’ll save money buying a Charlie card for the subway instead of paying for each trip individually.









Happy travels! I hope you love all the historic sites in Boston as much as we do!



Boston was the 4th stop along our American History road trip. Read about the rest of it here:

US History Road Trip With Kids

Washington D. C.: All the awesome things to see with kids

US History Road Trip: Battlefields, Philadelphia and NYC

Niagra Falls and Palmyra: Upstate New York

LDS Church History: Kirtland, Nauvoo and Winter Quarters




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