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100+ Wicked Awesome Things to Do in Boston, MA

Boston is the city I call home.

While I didn’t grow up here, I’ve lived here for 16 years and grew up not far away.

One of the reasons why I love this city so much is that there are so many things to do.

Check out my guide on over 100 wicked awesome things to do in Boston.

Take a tour

As touristy it sounds, taking a tour is a great way to kick off a trip.

A city tour can help you get a sense of the city layout.

Plus you might discover a neighborhood or attraction that you’d like to explore.

Check out my 5 favorite tours for a few ideas on what to do on your first day.

Aerial view of Boston and the Charles River with the tail view of a red helicopter in the corner.

Boston guided tours

One of the most popular tours is Boston Duck Tours.

This tour takes you through the city and into the Charles River in a World War II amphibious vehicle.

Boston Duck Tours is a great tour for families with kids.

Trolley tours are also a popular way to see the city.

I recommend Old Town Trolley Tours, as you can hop on and off at different stops along the route.

If you see something you want to explore, you can hop off, do some exploring, then catch the next trolley to continue on the tour.

Urban Adventours runs some great Boston bike tours.

On these tours you can bike part of the Freedom Trail, swing by Fenway Park, visit the North End, and more.

Boston helicopter tours are really taking off lately (ha! See what I did there?).

To catch one, you’ll need to head out to the suburbs, as there aren’t any operating within the city.

Boston Helicopters in North Andover, MA runs 4 different helicopter tours:

  • Boston city tour
  • Massachusetts coast
  • City/coast combo
  • Boston at night

If you’re looking for a more intimate look at a specific neighborhood, try Photowalks Tours.

Photowalks offers tours in neighborhoods like the Freedom Trail, North End, Beacon Hill or Back Bay.

Catch a sports game

Boston is a HUGE sports town.

We’re fiercely loyal to our sports teams, even when they’re in last place or go almost 90 years without winning a championship.

I’m looking at you, Red Sox.

The Boston Red Sox, featuring pitcher Matt Barnes in #32, playing at Fenway Park.

There are 4 major professional sports teams.

You’re bound to find a game to attend or cheer on at a local sports bar any time you are in town.

From Spring through late Summer or early Fall, the Boston Red Sox play baseball at Fenway Park.

The New England Patriots play football at Gillette Stadium in Foxborough, MA, from early Fall through early Winter.

TIP: Foxborough is about an hour outside the city, so you’ll need a rental car!

From Fall through Spring, the Boston Celtics play basketball at the Garden in downtown.

The Boston Bruins play hockey at the Garden during the same seasons, as well.

Aside from cheering on a sports team, you can also take a 1 hour walking tour of historic Fenway Park or visit The Sports Museum.

The Garden also occasionally offers behind-the-scenes tours, but only between sports seasons.

Visit a museum

Beantown has a reputation for being a world-class center for learning with its many schools, hospitals, and museums.

Ever since I was a child, my favorite museum has been the Museum of Science.

The Museum of Science is filled with tons of hands-on exhibits and experiences. There’s even a butterfly conservatory!

The New England Aquarium is another fun and educational spot.

The New England Aquarium has a variety of aquatic exhibits and animals. They also have a heavy focus on conservation and research.

If you are traveling with kids, the Boston Children’s Museum is a must-do, with its interactive exhibits and fun playscapes.

It’s is also home to several excellent art museums.

The Museum of Fine Arts (MFA) is home to an impressive collection of fine art, from historical and ancient artifacts to paintings, photography, and sculptures.

The Institute of Contemporary Art (ICA) specializes in contemporary art.

Aside from the usual types of art you’ll find at an art museum, the ICA also hosts musicians and DJS. They also coordinate art-focused trips to places like Bogota, Colombia.

Armless statue amidst large leaves and plants with a tan stone sidewalk nearby.

Another option for fine art is the Isabella Stewart Gardner Museum.

The Isabella Stewart Gardner Museum is home to a beautiful collection of fine art and gorgeous gardens. They also host musical performances.  

By the way – if your name is Isabella, you can apply for a card that grants you free admission for life! How cool and fun is that??

TIP: To learn how to visit some of these museums for FREE, check out my post about visiting Boston on a budget.

Browse magnificent libraries

The Boston Public Library (BPL) is the second largest library in the USA (The Library of Congress in Washington, DC is first).

The main branch is located in the heart of Copley Square, with 24 branches scattered throughout the city.

Interior view of a study room in the Boston Public Library Copley branch.

The Boston Public Library includes not just books, but also rare manuscripts and artifacts, art, musical scores, documents, and movies.

The BPL also hosts a variety of free events and offers a limited number of free museum passes to members.

Not far from the main branch of the BPL, is the Mary Baker Eddy Library.

The Mary Baker Eddy Library is home to the research and writings of Mary Baker Eddy, founder of Christian Science.

You can also visit the Mapparium, a 3-story stained glass globe of the world.

Over in Dorchester, next to the University of Massachusetts’ Boston campus, is the John F. Kennedy Presidential Library and Museum.

This library houses books, papers, and  other materials from former US President, John F. Kennedy, as well as a collection on Ernest Hemingway.

Explore gorgeous college campuses

I might be biased, as I went to graduate school at Northeastern University, but Boston is arguably the best college town in the USA.

It is home to institutions like Boston College, Boston University, Harvard University, Massachusetts Institute of Technology (MIT), Northeastern University, and Tufts University.

Snapshot of the oddly shaped Ray and Maria Stata Center built by famous architect Frank Gehry.

Many of these institutions offer tours for free.

One of the more popular schools in the area to tour is Harvard University, just across the Charles River, in Cambridge, MA.

To tour this Ivy League institution, I recommend the very fun “Hahvahd Tour,” led by real Harvard students.

Historical things to do in Boston

As one of the oldest cities in the USA, Boston is rich with historical experiences.

There are 3 things that standout as must-dos if you’re visiting to see historical attractions: The Freedom Trail, the Boston Tea Party Ships and Museum, and a ghost tour.

The Freedom Trail is a 2.5 mile trek from the Boston Common to the Bunker Hill Monument and the USS Constitution.

This popular urban trail takes visitors past 16 historically significant landmarks and sites, such as the Old State House, Paul Revere’s house, and the Granary Burying Ground.

The Boston Tea Party Ships and Museum take you back in time to one of the most significant events in US history.

There’s even an opportunity to throw some tea overboard one of the ships and a tea room for afternoon tea.

This last one might have you scratching your head.

But really, if you think about it, most ghost tours are just fun and spooky historical tours, right? Boston is no exception.

Ghosts & Gravestones is the best ghost tour in Boston.

The tour takes place at night aboard an old trolley.

To add to the spooky ambiance, the tour guides dress up as ghosts, too.

NOTE: This tour is NOT for families with young kids. Kids under 6 are not allowed and kids under 13 are discouraged due to loud noises and scary content.

Spend time outdoors

When many people think of a city environment, they assume there aren’t outdoor activities available.

That is definitely not the case for Boston!

Man paddleboarding in the ocean nearby Castle Island in South Boston

The Emerald Necklace

One of my favorite things to do in the city is hangout in the Boston Public Garden during the warmer months.

It’s a great spot for people watching, picnics, and leisurely walks.

TIP: The Public Garden is also one of my favorite places to photograph. If you’re looking for photo tips for the Public Garden, check out Photowalks’ Public Garden tour.

Across from the Boston Public Garden is the Boston Common.

The Boston Common includes 50 acres with sports fields, the Central Burying Ground (a cemetery from the mid-18th century), a bandstand stage, and a skating pond.

During the Summer, you can take a leisurely ride on a swan boat, too.

And please, whatever you do, do not call it Boston Commons. There’s no S at the end.

These 2 parks are part of a network of green space referred to as the Emerald Necklace.

Other excellent parks within this network include the Riverway, Arnold Arboretum, Jamaica Pond, and Franklin Park and Zoo.

The Rose Kennedy Greenway

Another network of parks across the city is The Rose Kennedy Greenway.

This includes various outdoor spaces in the North End, Fort Point Channel, Wharf District, Dewey Square, and Chinatown.

The section of the Rose Kennedy Greenway in the Wharf District includes a carousel and food trucks, as well as a seasonal beer garden.

The Charles River Esplanade

Another lovely green space to visit is the Charles River Esplanade, which runs between Boston and Cambridge, MA.

Portrait view of the Charles River Esplanade at sunset with a couple in a hammock between 2 cherry blossom trees.

There are a lot of activities available along the Charles River, such as bike and running paths, canoeing, kayaking, and sailing.

The Hatch Shell at the Esplanade shows movies during the Summer, as well as concerts and weekly Zumba classes.

The Wharf District

Yet another spot to hit up for some outdoor fun is the Wharf District, just outside the North End.

From the Wharf District you can join a whale watch, visit the Harbor Islands on a boat cruise, or experience the wild Boston Codzilla: Thrill Boat Ride.

Castle Island

Last up for outdoor activities is Castle Island in South Boston.

At Castle Island, visitors can tour Fort Independence and stroll along the beach.

Admire the skyline

Boston has a gorgeous skyline, especially with gorgeous sunrises and sunsets.

I definitely recommend checking out the skyline, even if it’s in the middle of the day.

Sailboats along the Boston Harbor with the city of Boston in the background. The sky is light blue, fading to pinkish orange.

Here’s an overview of my favorite spots to admire the Boston skyline.

On the Boston-Brookline border is Summit Avenue, a hill that stretches between Commonwealth Avenue and Beacon Street.

At the peak of the hill, you can take in a beautiful view of the Boston skyline from Corey Hill Outlook Park.

Another fantastic view of the city can be seen from across the Charles River on the riverbank along Memorial Drive.

If you don’t mind paying for the view, you can see the city from high up at the Skywalk Observatory or by securing a reservation at the Top of the Hub Restaurant & Lounge.

Both of these spots overlook the city from high up in the Prudential Tower.

Check out a brewery tour

Samuel Adams offers tours throughout the week, except for Sundays and holidays.

Tours last about an hour and include a tasting of classic and specialty brews.

Visitors can also pick up growlers of a small, rotating selection of brews.

Harpoon Brewery offers tours of their city brewery every day of the week, with the exception of holidays.

Tours at Harpoon Brewery also include tastings of classic and specialty brews.

All tours end at their on-site beer hall, where you can order full pints of beer and eat tasty pretzels.

For guided tours that visit multiple breweries and beer halls, check out the Boston Brewery Tour.

Aside from tours of local breweries, there’s also a constant stream of craft beer festivals in Boston.

Go on a shopping spree

If shopping is the main event for your trip, there are 5 key areas to hit up:

  • Downtown Crossing
  • Faneuil Hall
  • Newbury Street
  • SoWa Open Market
  • The Shops at Prudential Center and Copley Place
Landscape photo of the storefront for De Luca's Market on Newbury Street in Boston, MA, USA.

Downtown Boston includes a shopping district known as Downtown Crossing.

Downtown Crossing features a pedestrian mall with a variety of shops and stores, such as Macy’s, Marshall’s, TJ Maxx, Old Navy, and Primark.

Not far from Downtown Crossing is Faneuil Hall, another great district full of shopping and restaurants, such as Lucy’s League (a must for female sports fans), Newbury Comics, Boston Chowda, and Wicked Good Cupcakes.

Next up is the famous Newbury Street. Newbury Street is about a mile long and is lined with a mix of affordable and upscale retailers, independent boutiques, art galleries, and restaurants.

A few of my favorite shops on Newbury Street include Kiehl’s, Lush Cosmetics, Revolve Consignment, Sea Bags, Urban Outfitters, and Zara.

As for restaurants and cafes on Newbury Street, I frequent De Luca’s Market, Emack & Bolio’s Ice Cream, JP Licks, Lolita Cocina & Tequila Bar, Mother Juice, Stephanie’s on Newbury, and Thinking Cup.

Last but not least, are The Shops at Prudential Center and Copley Place.

While technically separate shopping centers, they are connected by a skywalk, so you can easily shop between the two.

Here you can hit up Sephora, Vineyard Vines, J. Crew, Neiman Marcus, or even stop for services at a Roman Catholic chapel.

The Shops at Prudential Center is also home to Eataly, an Italian food market that also houses several restaurants and food stalls.

Take a day trip

There are so many lovely New England towns within a short drive or train ride away from the city, that it would be wrong of me not to suggest taking a day trip away from the city.

Landscape view of the ocean in Provincetown and a rocky patch of land with a small shack. The sky is bright blue with a rainbow stretching out of a cloud above the shack.

Salem, MA is just a short drive or commuter rail train ride from Boston.

While Salem is lovely any time of the year, my favorite time to visit is in October, due to the month-long Halloween celebration.

Be sure to check out my post on Salem in October for tips if you decide to visit in the Fall!

If architecture is more your thing, take a day trip out to Newport, RI, where you can tour gorgeous mansions overlooking the ocean.

Provincetown, located at the very tip of Cape Cod, is another great option for a day trip.

To make the trip more doable as a day trip, I recommend taking the ferry from Boston to Provincetown, which takes about 90 minutes.

Provincetown is filled with lots of cute shops, restaurants, bars, and galleries. Provincetown is also a well-known LGBTQ friendly destination.

Another beautiful seaside destination is Martha’s Vineyard, which is accessible by plane and ferry.

Spend the day visiting a beach, shopping, boating, or fishing. Guided tours to Martha’s Vineyard from Boston are also available for a reasonable price.

For more ideas on where to go, check out my post about the best day trips from Boston.

What are your favorite things to do in Boston?

I hope you found the perfect activities for your trip to my home city.

Victoria

Thursday 20th of July 2017

First off I love that you named this Wicked Awesome hahaha I have heard so many people from Boston use this term. The one time I went to Boston and actually left the airport I ended up in Chinatown. It appears I have missed so much more. I will hold onto this until I return.

drivebytowns

Thursday 20th of July 2017

What a fantastic and comprehensive round-up! I'm not sure I could visit the library - I may never leave :-)

themormonadventurista

Thursday 20th of July 2017

Wicked awesome, huh? Love it! I studied American History in college and would be all over exploring the historical sites and pretending I'm in the newest "National Treasure" movie or something. And who could go wrong with a baseball game?! Although I'm no lover of the Red Sox, I would definitely put my ego aside to visit Fenway!

The Wanderlust Dietitian

Wednesday 19th of July 2017

omgosh! I am from the Southeast USA and have always wanted to "play" in Boston! I am definitely saving this post for that future trip!

Kristi Evans

Wednesday 19th of July 2017

Wow, the Boston library looks amazing!!! I'm adding that to my must see list for my next trip to the area.

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