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Top 15 Things to Do in Boston, Massachusetts

New England’s largest city is actually fairly small, but it’s got a long list of must-see attractions. It’s highly navigable, clean and home to an astonishing number of historical sites, luxury hotels and family-friendly sites. If you plan to visit, these top things to do will give you a great start at making the most of your time there.

Visit the Institute of Contemporary Art Boston Institute of Contemporary Art
Credit: Boston Institute of Contemporary Art by Smart Destinations via Flickr

Visit the Institute of Contemporary Art

What Is It? The Institute of Contemporary Art, referred to as ICA Boston by locals, is a lot more than just another art museum. 

Why Do It? Located on the South Boston waterfront, its spectacular space features performances, films and videos, presentations and galleries, filled with contemporary artists’ explorations of the physical and unseen world, though it’s arguably more well-known for its architecture than its art. 

Good to Know: Even kids will be mesmerized by the pieces displayed here because unlike most art museums, many of the works look more like stuff that’s familiar to them. Plus, youth 18 and under are admitted free to the museum.

Walk the Freedom Trail Boston
Credit: Boston by bigstock.com

Walk the Freedom Trail

What Is It? The 2.5-mile Freedom Trail is Boston’s top attraction, and walking it is really a must while you’re in the city. It’s one of the top free attractions in the city.

Why Do It? A red stripe marks the trail which traverses through the most historic neighborhoods in Boston, including 16 important sites pertaining to the Revolutionary War along the way. You’ll travel from Boston Common through Historic Downtown Boston, the North End, and finally, the Charlestown waterfront.

Good to Know: At the home of Paul Revere, you’ll get a very good sense of how people lived during the Revolutionary War years, and at the Old State Museum you can explore impressive memorabilia like the vial of tea that was salvaged from the original Tea Party crowd. It also includes the Old North Church, the spot where Paul Revered warned that the British were coming in 1775, sparking the American Revolution.

Jog, Bike or Walk the Charles River Esplanade  Charles River Esplanade
Credit: Charles River Esplanade by izik via Flickr

Jog, Bike or Walk the Charles River Esplanade

What Is It? This roughly three-mile stretch of leafy path sits along the Boston side of the River, running between the Museum of Science and the Boston University Bridge. 

Why Do It? The Esplanade is a great place to enjoy people watching, walk, jog, bike or rollerblade. If you’ve got kids, you can stop at the playgrounds along the way, and if you want to get out on the water, you’ll find places to rent sailboats. This area is also famous as the site of the nationally-broadcast Boston Pops Independence Day concert and fireworks.

Good to Know: While it attracts a ton of visitors during this time of year, at other times, you’ll find a lot more locals than tourists.

Explore Boston's “Secret Gardens” Boston
Credit: Boston "Secret Gardens" by boulter via Flickr

Explore Boston's “Secret Gardens”

What Is It? If you’d like to check out some of the city’s “hidden gems,” Boston has a number of so-called “secret gardens.” They’re hidden all over the place, nestled among concrete, on observation decks, in community rooms and more.

Why Do It? The Kendall Square Roof Garden is set upon the roof of a parking garage, and features 30,000 square feet of beautifully maintained gardens, with benches and picnic tables as well as an amazing view of the Boston skyline.

Good to Know:  The public atrium at 101 Merrimac Street is a veritable jungle, complete with exotic wildlife, a fountain and lush vegetation, while the sprawling Massachusetts General Hospital complex features a healing garden on the 8th floor. It’s got private nooks, comfy chairs, a well-manicured garden and spectacular views of Longfellow Bridge and the sailboats that glide along the Charles River in one direction, and Beacon Hill on the other.

Visit the Observation Deck at Custom House Custom House
Credit: Custom House by wikimedia.org

Visit the Observation Deck at Custom House

What Is It? The observation deck at the Custom House in Downtown Boston is another great place to take in incredible vistas. The open-air observation deck offers panoramic views of the harbor and the city from the 26th floor. 

Why Do It? For many years, the magnificent neoclassical landmark sat empty and inaccessible in the heart of the Financial District, but in the 1990s, it reopened as a Marriott time-share hotel. 

Good to Know: A short climb up a staircase offers the chance to check out the vast grand rotunda, which is now a maritime-themed exhibition space.

Tour Samuel Adams Brewery Samuel Adams Brewery
Credit: Samuel Adams Brewery by Samuel Adams Brewery

Tour Samuel Adams Brewery

What Is It? While it may be considered a bit touristy, taking a Samuel Adams Brewery Tour is free and you’ll get to enjoy a free beer as well as sample ingredients that are used. 

Why Do It? The tour of this major Boston brewer provides an excellent and entertaining overview of the craft brewing process, where you’ll learn all about the history of the brand while smelling the Hallertau hops used to brew Sam Adams. 

Good to Know: Tours depart every 45 minutes, though it’s best to arrive early in the day to avoid a long wait. Under 21s are welcome, but obviously cannot partake in drinking.

Catch a Game or Take a Tour of Fenway Park Boston, Massachusetts
Credit: Boston, Massachusetts by bigstock.com

Catch a Game or Take a Tour of Fenway Park

What Is It? Just about every baseball fan puts visiting Fenway Park on their bucket list. Even if you aren’t a baseball fan, going to a Boston Red Sox game is a great way to get to known Bostonians. 

Why Do It? This iconic ballpark that sits smack in the middle of the city is a perfect place to gawk at those legendary Red Sox fans, but if you can’t get tickets to a game or the team is out on the road, you can still take a tour of the stadium – something that most Boston residents rarely do.

Good to Know: You can also grab a beer at the Bleacher Bar, built under the stands, or at the Cask ‘n Flagon, which prides itself on being “the second-best baseball bar in America.”

Visit the Museum of Science Museum of Science
Credit: Museum of Science by Museum of Science

Visit the Museum of Science

What Is It? The Museum of Science has long been one of the most popular museums in Boston.

Why Do It? Your kids will never get bored here, though adults love it here too. Especially kid-oriented, it offers the chance to learn about earth sciences, anatomy, and astronomy through the fun interactive exhibits like the “Dinosaurs: Modeling the Mesozoic” in which they can learn about paleontologists and fossils. The “Live Animal Care Center” is another permanent exhibit offering kids the chance to see live animals and learn about the impact humans have on them. 

Good to Know: Don’t miss checking out the full-size models of the Apollo and Mercury capsules, the butterfly and insect garden, and a billion-year-old boulder. The museum also hosts a planetarium, to indulge their, and your, inner astronaut, and the Mugar Omni Theater which features IMAX films that will make you feel as if you’re actually in the movie.

Step Into the Boston Public Library Boston Public Library
Credit: Boston Public Library by bigstock.com

Step Into the Boston Public Library

What Is It? This is the oldest large free-lending library in the nation, designed as a “palace for the people.”

Why Do It? Visit a library while on vacation? While it might not seem like it would be something enjoyable to do, visiting the Boston Public Library, which opened in 1895, is different than a visit to most. One of its highlights is the awe-inspiring Bates Hall, its stunning reading room. It’s also the only library to host a Presidential Library, that of John Adams, America’s second president.

Good to Know: Other prominent features include a number of vast murals by noted artists, like a series by John Singer Sargent, as well as the Italian Renaissance-style interior courtyard, complete bubbling fountains and arched pathways.

Explore Rose Kennedy Greenway Rose Kennedy Greenway
Credit: Rose Kennedy Greenway by mcgrayjr via Flickr

Explore Rose Kennedy Greenway

What Is It? The Rose Kennedy Greenway is made for walking, as a nearly one-and-a-half-mile series of parks, gardens and walkways that link the city’s diverse neighborhoods.

Why Do It? The only organically maintained public park, and one of a handful of organically maintained urban parks in the entire country, it also features changing public art displays, numerous food vendors, a carousel and bubbling fountains. 

Good to Know: Free weekly events like live music performances, fitness classes, photography exhibits and artisan craft markets are held here too.

Tour the USS Constitution USS Constitution
Credit: USS Constitution by bigstock.com

Tour the USS Constitution

What Is It? One of the most interesting sites in Boston is the USS Constitution, the oldest commissioned warship afloat in the world.

Why Do It? First launched in 1797, it was one of six ships that were ordered by George Washington to protect the growing maritime interests in America. Its greatest glory came during the war of 1812, defeating four British frigates which earned her the nickname “Old Ironsides,” because cannonballs glanced off the thick hull. In 1927, the ship was restored, thanks to contributions from schoolchildren around the nation. 

Good to Know: Free tours are conducted by Navy crew members, and they’re popular with kids and adults alike.

Check Out Charles Street Meeting House Charles St Meeting House
Credit: Charles St Meeting House by bigstock.com

Check Out Charles Street Meeting House

What Is It? Located in the vibrant, historic Beacon Hill neighborhood, the Charles Street Meeting House, built in 1804, was a major player in the city’s abolitionist movement and saw speakers like William Lloyd Garrison, Charles Sumner and Soujourner Truth, just to name a few. 

Why Do It? Since then, it’s been home to three congregations, progressive causes, retail stores, a residence and offices. In 1920, it dodged demolition, literally, by being moved ten feet toward the river to make room for the widened Charles Street. It was saved again in the 1980s, taking on new life. 

Good to Know: Today, it offers a wide range of cultural and historical opportunities for history buffs and all types of travelers, with charming cafes and shops.

Take in the Views From the Bunker Hill Monument Bunker Hill Monument
Credit: Bunker Hill Monument by bigstock.com

Take in the Views From the Bunker Hill Monument

What Is It? The Bunker Hill Monument stands 221 feet tall at Breed’s Hill, the site of the first major battle of the American Revolution fought on June 17, 1775. 

Why Do It? This nationally recognized historic landmark also offers some of the best views in Boston, but you can’t take an elevator to the top, you’ll have to climb the 294 steps to get there. Most feel the amazing vista at the end is a reward well worth the effort. 

Good to Know:  Admission is free, but because of high visitation and for safety requirements, all visitors who wish to climb the monument must obtain a free climbing pass from the Bunker Hill Museum located at the base of the hill at 43 Monument Square.

Watch the Stars at Public Open Night at the Observatory Public Open Night at the Observatory at Boston University
Credit: Public Open Night at the Observatory at Boston University by bu.edu

Watch the Stars at Public Open Night at the Observatory

What Is It? The Public Open Night at the Observatory at Boston University provides the opportunity to observe the night sky through telescopes and binoculars, possibly see things you might otherwise not get to see, and learn a bit about astronomy too. 

Why Do It? Held most Wednesday evenings throughout the year, weather permitting, everyone is welcome to come, and the program lasts about an hour. 

Good to Know: The Judson B. Coit Observatory is located on the roof of the College of Arts & Sciences building at 725 Commonwealth Avenue.

Look for Keytar Bear Keytar Bear
Credit: Keytar Bear by ursonate via Flickr

Look for Keytar Bear

What Is It? While you probably won’t see this on most “Things to Do” lists, searching for the Keytar Bear is a fun and more unique way to spend some time in Boston.

Why Do It? Keytar is one of the city’s most beloved street performers. While he’s more than a little unconventional, he’s definitely a true find that helps make his city stand out. His supporters are so loyal, they started an Indiegogo campaign after some ruthless people beat and robbed him, and managed to raise more than $5,000 to help Keytar out. 

Good to Know: Look for him perched on the platforms along various MBTA (subway) lines, strapped with his portable piano and donning a ruffled yet slightly-fluffy animal costume – he has captured the hearts of the commuting public, and he’s sure to capture yours.

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