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Explore 20 Must Do Experiences In Boston

Boston, Massachusetts. Home to the Boston Marathon, the fictional bar Cheers, and the Boston Commons. It’s also home to some of the greatest events in U.S. history and a place where history continues to live in its cobblestone streets, neo-federal architecture, and in the volumes of books in the Boston Public Library. 

Given that its founders birthed America as we know it today, it’s no exaggeration to say that when you visit Boston, you’re visiting home, even if your physical residence is located someplace else. It’s a shiny city on a hill that held and still holds the promise of the nation.

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A visit here is worth savoring, and these 20 sites are among the best places to see the city shine.

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1. Ride a Swan Boat in Boston's Public Garden

You haven’t taken a pedal boat ride until you’ve set sail on one of Boston’s swan boat rides. While they run with the same technology that all pedal boats do – by the power of feet – the swan boats in the park certainly do it more beautifully than most. 

At the back of the boat, a stunning swan hides the pedals and the captain powering the boat. Riders sit on benches and enjoy a 15-minute boat ride around the lake. 

The addition of the swan got its inspiration from the medieval German story of the knight, Lohengrin, who is said to have ridden across a river in a swan-powered boat to rescue his princess. Swan boat riders have enjoyed this tale since 1877, making it one of Boston’s most important and longest-running tourist attractions.

2. Explore Faneuil Hall

Long before the United States proclaimed its independence from Britain, there was Faneuil Hall. Established in 1742, Faneuil Hall holds the distinction of being the place where the Boston Tea Party took place, as well as being a meeting hall and public marketplace. It is affectionately known as the “Cradle of Liberty.”

Today, it’s still a place where people meet up, and while any tea spilled now is likely at the local tea shop, it’s still a happening place. If you visit, you’ll find myriad artisan shops, excellent eateries, and a jumping off point for other attractions of note in the city.

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3. Go to Fenway Park for a Baseball Game

Since its opening in 1912, Boston’s Fenway Park has given a home to both the Boston Red Sox and America’s favorite pastime. Given its history, it’s probably safe to say that you’ven’t seen a baseball game until you’ve seen one at Fenway.

And if your visit to Boston doesn’t land on a day when the Red Sox bats are swinging, Fenway still has a lot to offer. The park hosts regular tours, allowing baseball fans to get a behind-the-scenes look at one of the most important sites in baseball history.

4. Ice Skate on Frog Pond in the Boston Common

In the 1600s, people gathered in Boston Common to take part in the Revolution. In the 21st century, they come to skate on Frog Pond in the winter. Granted, people gather in the oldest public park in the U.S. for lots of other reasons, too, but taking part in a public skate may be one of the most enjoyable reasons why they come here.

The pond opens daily for skating, with exceptions for the December holidays. Admission is $8.00 and rentals are available.

5. Have Some Seafood

Boston’s location makes it one amazing seafood town, and no trip to Boston is complete without trying a plate of lobster rolls, oysters, and fish cakes at one of Boston’s many seafood restaurants. And any seafood restaurant tour in Boston worth its salt must begin with Union Oyster House, the oldest continually-run restaurant in the U.S. Union Oyster House began serving food in its establishment in the early 1800s.

It’s located just a stone’s throw away from Faneuil Hall on the Freedom Trail. In its stalls, a future king of France, the wives of revolutionary statesmen and presidents, and more than a few common folks ate dinner and even planned the beginning of a new nation. When you eat oysters here, you’re not just filling your tummy. You’re filling your internal history books, too!

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6. Visit Boston Museums

Boston’s long history means that it offers a lot in the way of culture. As such, it counts among the great museum cities of the world. While we could freely recommend all of Boston’s museums, we understand that your time in Boston may be limited.
Therefore, if you must choose only a few museums, then start with these:

  • Isabella Stewart Gardner Museum: Built in the late 1800s and early 1900s, this museum houses the art collection of Isabella Stewart Gardner and features important works from American, Asian, and European art. It also holds the distinction of being the site of one of the most-famous, and yet unsolved, art heists in history.

  • Museum of Fine Arts: This impressive museum houses more than 8,000 works of art and counts among the largest museums in the world.

  • Institute of Contemporary Art: This sister to MoMa got its start in the mid-1930s and has been a significant voice in contemporary art, not only in Boston, but in the world, since then.

  • The Mary Baker Eddy Library: This museum houses the major works of Mary Baker Eddy, the founder of Christian Science.

  • Boston Tea Ships & Museum: You’ll relive the legend of the Boston Tea Party at this famous museum. It’s filled with interactive exhibits and full-scale ship replicas. The exhibit even has onsite actors bring extra life to the experience!

7. Take a Tour of Beacon Hill, Beacon Street, and Acorn Street

Boston’s old streets keep much of America’s history alive and relevant, and some of the best ways to take a deep dive into Boston and U.S. history is by lacing up your walking shoes and exploring some of Boston’s most famous streets and neighborhoods.

Beacon Street is an excellent place to start your tour. It leads to Beacon Hill, Boston University, and more. As you walk down its cobblestone streets and admire the old gas lamps, you can practically hear the cries for revolution and the laughter among friends in the old pubs. And if that isn’t enough beauty for you, then you won’t want to miss taking a trolley ride down Acorn Street, one of America’s oldest and now most prestigious neighborhoods.

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8. Explore Boston’s Irish Pubs and Culture

Irish culture is alive and well in Boston, and the city’s Irish pubs offer you an excellent place to experience that culture first-hand. Given that the Guinness always runs fresh at these establishments and Irish foodstuffs dominate the menu, they’re a great place to rest your tired feet after a day of exploring and sight-seeing.

9. Walk the Freedom Trail and Tour the USS Constitution

Boston’s Freedom Trail, a two-and-a-half-mile trek through history, takes visitors past 16 of the most historically significant landmarks in the U.S. Some of them, like the Boston Common and Faneuil Hall, have already made our list.

Other sites of significance include the Paul Revere House, the Old Corner Bookstore, and the USS Constitution, also known as “Old Ironside.” For naval history buffs, Old Ironside is particularly worth a second look; it’s the oldest commissioned warship and one of the most impressive masted ships afloat.

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10. Play Along the Charles River

This 80-mile-long river flows from Hopkinton to Boston and attracts numerous water sports enthusiasts in the warmer months. Its long stretch is dotted with boat houses, regattas, and plenty of history.

On any given day, you’ll find people wandering the docks, taking a Duck Boat tour, or trying their hand at kayaking or canoeing.
Or if you’re not up for water sports, the Charles River still has plenty to offer. Taking a walk through the Esplanade Park along the river is a perfectly good way to spend the afternoon.

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13. Explore the Boston Harbor Islands

Consisting of 34 islands and peninsulas, the Boston Harbor Islands are like magical wonderlands, just waiting to be explored. On any given day, a trip around the islands might net you an adventure in an old fort, immerse you in the history of area lighthouses, offer you unbelievable hiking experiences, or the camping adventure of a lifetime, complete with a yurt under the stars.

This oasis of natural beauty sits only minutes from downtown Boston and lightyears away from the ordinary. It’s a bucket list experience for sure!

14. Shop on Newbury Street & Explore the Back Bay & Copley Square

If shopping at world-class stores like Ralph Lauren, Marc Jacobs, and Chanel appeals to the fashion lover in you, then you’ll find no better place to shop in Boston than on Newbury Street and the Back Bay.

And if you run out of top notch places to shop on Newbury Street, then make your way over to Copley Square, where you’ll find Saint Laurent and Gucci. Along the way, you’ll encounter some of the most stunning and historic architecture, not only in America, but in the world.

11. Explore Boston's North End

Boston’s Little Italy isn’t just home to those of Italian descent, though its large Italian population was enough to give the North End the “Little Italy” moniker. Colonized since the 1600s, this neighborhood holds the distinction of being the place in the U.S. where European settlers (and those of European descent) have lived without interruption for the longest amount of time.

Tourists can take a self-guided tour of Boston’s North End, trying out local pizzerias, pastry shops, and more along the way.

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12. Visit Boston's Parks

Boston’s parks are as green as Irish fields and just as charming. And fortunately for outdoor lovers, Boston and the surrounding area boasts a lot of them.

If you don’t know where to start, then try the Emerald Necklace on for size. What’s the Emerald Necklace, you ask? Why, it’s a 1,100-acre chain of parks in the Boston area, connected by waterways and parkways.
You likely already know of a couple of parks on the chain. Both the Boston Common and the Public Garden that we mentioned earlier are among the parks on the necklace, but there’s so many more just waiting for you to explore!

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15. Tour the Boston Public Library

The Boston Public Library at Copley Square will take your breath away. That’s no exaggeration. Take just one look at its grand arched ceiling, exquisite chandeliers, and world-class artwork, and you’ll understand why it’s not necessary to tell anyone to keep their voices down in the library. The awe factor alone takes care of that.

Aside from its stunning beauty, it’s a place of rich history. It is America’s first large free municipal library and its walls have great stories to tell. Book an art and architecture tour to fully immerse yourself in the library’s great story.

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16. Explore the Mount Auburn Cemetery

Without knowing it, most of us owe a great deal to the Mount Auburn Cemetery. Although all of us have visited at least one cemetery or park throughout the course of our lives, we probably haven’t given much thought to it (aside from what the occasion for being there required).

But the fact that we’ve even been to a public cemetery or municipal park has everything to do with the Mount Auburn Cemetery. It was the nation’s first garden or rural cemetery. Before Mount Auburn Cemetery, people were buried on church grounds and public open spaces were scarce. Its existence began the movement toward public parks and open spaces in the United States.
Many prominent members of Boston society are buried there. Its grounds also host an arboretum. The grounds are open from 8:00 a.m. to 5:00 p.m. and public restrooms are available to visitors.

17. Explore the Seaport District

Boston’s Seaport District brings together the history of the Boston Harbor with the sensibilities and trappings of modern life. Numerous shops and restaurants, as well The Boston Convention and Exhibition Center, the Reebok shoe company, eight hotels, the John Joseph Moakley United States Courthouse, the Institute of Contemporary Art, and myriad residential buildings all call the Seaport District home.

But aside from providing a physical home for these businesses and homes, it’s also a home to innovation. In fact, this South Boston district has earned the nickname “The Innovation District.” What’s most remarkable about this area is that for most of the history of the city, up through the 20th century and beyond, this area was mostly parking lots and forgotten wharfs. It’s a true testament to city planning and innovation.

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18. Learn About The History and Architecture at the Massachusetts State House

Sitting across from the Boston Commons, the Massachusetts State House stands as a bastion of architecture and history.

Aside from being one of the crowning achievements of America’s first professional architect, Charles Bulfinch, some of the most important events in U.S. history took place in this Beacon Hill landmark. Oliver Wendell Holmes was only slightly exaggerating when he called it the “hub of the solar system.”

Completed near the turn of the 19th century, this Freedom Trail must-see began as a cornerstone, laid down by none other than Samuel Adams and Paul Revere. Its neoclassical-federal style was inspired by Greek and Roman temples and the hope for the future of our democracy. It’s worth noting that its architect, Charles Bulfinch, was only in his 20s when he designed the Statehouse.

Some 200+ years later, it’s still a place of incredible architectural details, stunning artwork, and important cultural artifacts. If you’re taking the Boston Freedom Trail Tour, it’s definitely worth a stop-off.

19. Climb the Bunker Hill Monument

When you climb the 294 steps up to the Bunker Hill Monument, you put yourself in-step with the soldiers who fought the Battle of Bunker Hill centuries ago. The bloody battle took place on the hilly landscape across from the Charles River.

That famous battle claimed hundreds of lives, and although the British took the victory by battle's end, that victory came at a great cost. British casualties were double that of the colonists, and their losses included a great number of officers.

Today, a 221-foot tall granite obelisk stands as a memorial to the battle and the soldiers who fought there. Visitors can climb the steps of the monument and tour the associated museum.

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20. Immerse Yourself in Boston’s History

Each of Boston’s architectural wonders and historic artifacts represent a different chapter in the history book that is Boston, and ultimately, America. If a visit to each of the previous suggestions leaves you hankering to learn more about Boston, its history, and its architecture, then we’d also like to recommend that you visit these Boston must-sees.

  • The King’s Chapel: A place of importance not only in Christian Unitarian history, but also in architectural history, the King’s Chapel offers visitors one of the best examples of the work of Peter Harrison, the noted colonial architect. It’s now a National Historic Landmark.

  • Old South Meeting House: Although the Boston Tea Party took place in the Boston Harbor, the ideas for it began in the Old South Meeting House. Aside from that, it was the place where Benjamin Franklin’s baptism took place and the spiritual home of the first published Black poet, Phillis Wheatley.

  • Old State House: Throughout Boston’s history, storms raged, fires burned, and revolutions were spawned, and through it all, the Old State House remained standing. It’s the longest-standing public building in Boston and a National Historic Landmark.

  • Granary Burying Ground: Created in the mid-1600s, this cemetery gets its name from the grain storage building that once stood nearby. It also holds the distinction of being a place where some of the U.S.’s most notable people have been laid to rest and is one of the oldest cemeteries in the country.

  • Old North Church: While the name of the Old North Church may not be very well known, Paul Revere’s ride and his famous statement, “one, if by land, two, if by sea” certainly is. As the first stop on Paul Revere’s famous midnight ride, this landmark will forever hold a place of significance in American history.

  • Paul Revere House: The home of one of America’s Founding Fathers counts among the most important and significant places in the history of Boston and the U.S. A trip to the Paul Revere House offers tourists a deep dive into the life of this great American patriot.

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Final Thoughts

A trip through Boston is a trip through American history. Each of the sites on this list offers visitors a look at Boston through a different lens, and taken together, each one gives city visitors a more complete look at the history of a city that changed the nation and the world.

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