18 Quintessential Must-Do’s In Boston That You Can’t Miss

Where you’ll find things steeped in history.

LAST UPDATED: December 5, 2021.

As the capital and biggest city of Massachusetts, Boston has no shortage of awesome things to do. It’s also one of the oldest cities in the entire United States, so no matter where you go, you’ll find things steeped in history. Whether you’re visiting just for the day or for longer, here’s a list of our top must-do’s and must-see’s in Beantown.

Walk through the Freedom Trail.

Freedom Trail Foundation
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Most likely the most iconic 2.5 miles in Boston is the Freedom Trail, where you will stop at 16 landmarks that begin from Boston Common, through downtown to North End and eventually end at Bunker Hill Monument. Sites include: Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel and King’s Chapel Burying Ground, Boston Latin School Site/Statue of Benjamin Franklin, Old Corner Bookstore, Old South Meeting House, Old State House, Boston Massacre Site, Faneuil Hall, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, USS Constitution, and Bunker Hill Monument.

Wander Around Faneuil Hall Marketplace.

4 S Market St, Boston, MA 02109

Faneuil Hall Marketplace
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Faneuil Hall Marketplace consists of four buildings: Faneuil Hall, Quincy Market, North Market and South Market. Faneuil Hall is the oldest with a long and important history in the real of Massachusetts politics. Samuel Adams actually once stood there to push for resistance against the British. Quincy Market is a lively marketplace full of interesting souvenirs and an abundance of culinary options from all over the world. The North and South Markets hold many boutiques if you want to do a little shopping. This area is also great if you want to go out at night with friends, as there are multiple bars that are worth checking out.

See a Sox Game at Fenway or take a tour.

4 Yawkey Way, Boston, MA 02215

Boston Red Sox.
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Whether or not you’re a baseball fan, you have to check out Fenway Park. What makes it so special is that it is one of the last two “old-school” ballparks in Major League Baseball (the other being Wrigley Field in Chicago.) The Green Monster (the super high left field wall) and its scoreboard are two of the most famous pieces of Fenway. While most ballparks have electronic scoreboards now, Fenway still has one completely posted by hand. Many homeruns or line drives that would normally have cleared the walls in other ballparks fail to make it over the Green Monster. Babe Ruth of the Yankees was the first opposing player to hit a home run over it, but don’t let Boston fans hear you talk about the Yanks or you’ll be in for some nasty remarks.

Admire masterpieces at the Museum of Fine Arts.

465 Huntington Ave, Boston, MA 02115

Museum of Fine Arts, Boston
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While most people think of New York as the art capital of New England, you shouldn’t disregard Boston so quickly. It has several great art museums, but the two you should definitely check out are the Museum of Fine Arts and the Isabella Stewart Gardner Museum (next.) The Museum of Fine Arts is, in fact, one of the oldest art institutions in the country (are we seeing a trend yet,) and its Art of the Americas wing is one of the most celebrated collections of American Art.

Step inside the Isabella Gardner Museum.

25 Evans Way, Boston, MA 02115

Isabella Stewart Gardner Museum
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A few blocks away from the Museum of Fine Arts, you’ll find the absolutely gorgeous Isabella Stewart Gardner Museum. The museum is designed to look like the Palazzo Barbaro in Venice and houses Isabella’s impressive collection of Italian art. The museum was the target of a major theft that became the focus of a Netflix documentary in recent years. For more details and fun facts about the museum, read more here.

Have a picnic at Boston Common.

139 Tremont St 1B Charles St 38 Beacon St 167 Tremont St, 115 Boylston St, Boston, MA 02116, United States

Boston Common.

Boston Common is a public park and the oldest one in the U.S. since 1634. Not only is it an ideal spot for a picnic, you can also rent a boat and enjoy a relaxing time on the water. It’s also within walking distance from the Public Garden, Massachusetts State House and the original Cheers pub that has become iconic from the long-running television show.

Browse through contemporary art at Underground at Ink Block.

90 Traveler St, Boston, MA 02118, United States

Underground at Ink Block
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To inhale the modern and street art creativity of Boston, check out Underground at Ink Block located near Downtown. Also catered to cyclists, there are bicycle paths, fitness classes and bike storage facilities. The whole area is an innovative space which features artwork by local and international artists. You’ll also experience Boston’s first mural project, interactive installations, exhibition and cool events,

Stroll Boston Harborwalk and discover the Waterfront neighborhood.

Boston Harborwalk
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Boston Harborwalk is a lovely location to run, kayak, or cycle along the Boston Harbor shoreline, which extends from East Boston to Neponset River via 47 miles. The heart of the Harborwalk features several notable sculptures, including: Playful Fish Beach by Judy Kensley McKie, and Untitled Landscape by David von Schlegell. The Harborwalk also boasts nine public beaches, or you can opt to stop during the walk at the Envoy Hotel’s rooftop bar for a breathtaking view of the city.

Geek out inside the Museum of Science.

1 Museum Of Science Driveway, Boston, MA 02114

Museum of Science, Boston
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The Museum of Science is home to over 700 interactive exhibits and presentations spanning from anatomy to earth science. It features occasional rotating special exhibits that are fun and educational for all ages. The museum also houses the Charles Hayden Planetarium for those who have a love of astronomy.

Tour one of the iconic breweries.

Harpoon Brewery
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If you need to quench your thirst after a long day of sightseeing, then sign up for one of Boston’s famous breweries. Whether it’s Harpoon or Samuel Adams, the brewery tours are great dives into the city’s elongated relationship with beer from the 1600’s through the Puritan era, to modern times. If you prefer to taste indie microbrews, there are more than several scattered throughout Boston, spanning from fruity pale ales to crispy pilsners.

Explore the North End neighborhood, Boston’s Little Italy.

north end boston
Photo by Akhil Dakinedi on Unsplash

Arguably the most charming district in Boston, a trip wouldn’t be complete without wandering aimlessly in North End. Reeling back to the 1600s, the English Puritans settled upon the city’s oldest streets and gave North End its signature architecture style: cast-iron buildings, embellished brackets, diamond panes on window frames. Once Italian immigrants came through, the neighborhood’s food scene truly flourished. On Hanover Street, don’t miss cannolis and Italian bread at Bova’s Bakery, or pies and biscottis at Modern Bakery. Regina Pizzeria has been around since 1926, serving the city’s iconic brick-oven, thin-crusted slices.

Indulge the beauty of nature at Charles River Esplanade.

Charles River, Esplanade, Boston, MA 02116, United States

Charles River Esplanade
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A fantastic way to discover the Back Bay neighborhood is to stroll through Charles River Esplanade – a gorgeous public park where you can people watch, drink craft beers at pop-up shops and find a grassy spot to picnic along the water. The park features a plethora of gardens, ponds, playgrounds for kids, and bridges for the perfect photo opp. If you’re a fan of kayaking, start at Community Boathouse.

Explore the scientist in you at the New England Aquarium.

1 Central Wharf, Boston, MA 02110

New England Aquarium
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If you’re a fan of marine sciences, then the New England Aquarium is a must-see. It has a ginormous, four-story fish tank full of beautiful sea life that you can spend hours ogling at. It also has your typical stingray touch pool and an awesome penguin habitat – a star attraction.

See Boston through a different lens at Rose Fitzgerald Kennedy Greenway.

Atlantic Ave, Boston, MA 02110, United States

Rose Kennedy Greenway
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The Greenway is a 1.5-mile stretch over several parks throughout downtown Boston. It’s a hub of festivals, gardens, sculptures, memorials, art installations, and best of all: food trucks! If you’re there with young kids, the carousel is a perfect place to take them on a spin. Trillium Beer Garden on the Greenway is a fantastic spot to taste various IPAs and other types of local brews. The open market is a delightful shopping venue for souvenirs made by local artisans.

Get historical at the JFK Library and Museum.

Columbia Point, Boston, MA 02125

John F. Kennedy Presidential Library and Museum
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If you’re a history buff or just love JFK, this museum will feed your soul. It’s in the Dorchester neighborhood, so a little off the beaten path but well worth it for its collection of artifacts, photos and videos about the Kennedy’s. The building itself sits right on the water and offers a breathtaking view of the city skyline. You’ll see items from both his presidency and his personal life, including a display on the late Jackie Kennedy Onassis which incorporates some of her famous outfits. It even has Kennedy’s 26-foot sailboat, and a recreation of the television studio in which he debated Richard M. Nixon in the 1960 election.

Set sail on the USS Constitution.

93 Chelsea St, Charlestown, MA 02129, United States

USS Constitution Museum
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Well…sort of. Also known as Old Ironsides, the USS Constitution is the world’s oldest ship still afloat. The name was submitted to President George Washington and it was one of the six original frigates approved to be constructed under the Naval Act of 1794. Today, you can visit “America’s Ship of State” via a tour at the museum filled with artifacts and interactive displays that explain the ship’s history and significance within the prestigious institution of the U.S. Navy. The USS Constitution is also part of the Freedom Trail.

Stop by the Boston Tea Party Ships & Museums.

306 Congress St, Boston, MA 02210, United States

Boston Tea Party Ships & Museum
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Are you a patriot? Voted as the most patriotic attraction, the Boston Tea Party Ships & Museum offers a fun one-hour long tour fitting for the entire family. Travel back in time and experience one of the most significant events that led to the American Revolution as the country fought for its independence. The museum takes you through the Meeting House where Samuel Adams plays host, Griffin’s Wharf, 3D reenactments, The Robinson Tea Chest, Abigail’s Tea Room…and much more.

Be inspired at The Institute of Contemporary Art.

25 Harbor Shore Dr, Boston, MA 02210, United States