14 Fun Things to do in Boston

What’s the fun in visiting a city only to do things that you can do anywhere else? My goal when exploring a new destination is to immerse myself in activities that accurately depict that city. Boston is one of those places where it’s easy to find activities that are well…..uniquely Boston. Full of world class museums, quaint neighborhoods, plus tasty food and drink, it’s no surprise you’ll find plenty of things to do in Boston.

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Things to do in Boston

Boston, the capital of the state of Massachusetts, has a lot to offer. The history alone makes it worth visiting. Throw in a beautiful waterfront location, exciting sports teams and interesting surrounding areas and you’ve got a city worthy of a visit on its own or one that can be included in a New England road trip.

In fact, my first introduction to the city was on a Boston to Bar Harbor road trip with my daughter. Inside the city proper – and with maybe a side trip to Cambridge – you’ll find plenty of fascinating and fun things to do in Boston to keep you busy. Here’s a few suggestions to get you started.

Discover Boston on a Walking Tour

As a first-timer or even an experienced visitor, one of the best things to do in Boston is to take a tour to learn about the city and have fun while you’re doing it. The Freedom Trail walking tours are a great choice because they showcase a collection of historical sites from 17^th – 19^th century Boston while telling the story of the American Revolution. 

Depending on who you book your tour with, you can choose from a variety of tour options including Walk into History, Revolutionary Women, African-American Patriots, Historic Pub Crawl and more. Most walking tours cover a distance of one mile or less and take 90 minutes. The best part is – they are led by a tour guide in an 18^th-century costume!

Be sure to leave some time after your tour for a more in-depth visit to some of your favorite attractions from the tour. The Aloft Boston Seaport hotel is convenient to the airport, convention center and the redeveloped South Boston Waterfront area with restaurants and bars.  

Recommended by Jenny from Global Game Plan

• Boston Town Crier
• 139 Tremont St, Boston, MA 02111
• 617-794-7512

Ride a Trolley

To switch it up, instead of walking the streets of Boston take the trolley ride through the city. The Old Town Trolley offers a variety of tours and packages throughout Boston. This mode of getting around is especially good for first-time visitors and is easier for families with small children.

You can choose from one or two day hop on hop off, city tours that includes all the major areas like Downtown, Beacon Hill, Back Bay, the Theater District, and the Waterfront District or book a themed tour. There’s a spooky Ghosts and Gravestones tour and a Boston Tea Party Ships and Museum tour available plus other seasonal offerings for holidays and in summer.

The trolley tours are a convenient and affordable way to see the city when you don’t have much time or don’t have a car.

• Old Town Trolley
• 200 Atlantic Ave, Boston, MA 02110
• parking available nearby

Indulge in Boston Cream Pie

It wouldn’t be a trip to Boston without indulging in a dessert named for the city itself. It’s believed that this dessert, really more cake than pie, was first made in 1856 by Armenian-French chef M. Sanzian at the Parker House Hotel in Boston. 

The cake has two layers of sponge cake filled with gooey custard and brushed with a rum syrup. Then toasted sliced almonds are overlaid on the sides and the top is covered with pliable chocolate fondant. According to Wiki – other custard cakes may have existed at that time but baking chocolate as a coating was a new process, making it unique and a popular choice on the hotel menu.

Boston Cream Pie can be found all over the city. Of course, you can pay a visit, or stay, at the Omni Parker House Hotel to try the original, still on the menu, or book a Boston food tour that includes a sample this delicacy and other local flavors.

• Omni Parker House
• 60 School St, Boston, MA 02108
• 617-227-8600

Sailing in Boston Harbor

Boston Harbor is one of the most beautiful and historic sailing areas in the world. With its strong currents and rich history, the harbor is a popular destination for both experienced and beginner sailors alike. Visitors to the harbor can enjoy stunning views of the city skyline. Standing on the deck of a boat, you can get a sense of just how large and varied the architecture of Boston is. 

And, of course, the harbor is a sight to behold, with both massive ships and small boars navigating it simultaneously. Additionally, sails will come with excellent commentary on the harbor’s history making it a great way to learn more while enjoying the cruise! 

The harbor is home to a number of different sailing clubs and organizations, making it easy to find a group to sail with. Boats will range from 100-person cruises down to a small boats for just a couple of people allowing you to customize your experience!

Whether you’re looking for an exhilarating experience or a relaxing afternoon on the water, sailing on the Boston Harbor is sure to be a highlight of your trip to Boston. Recommended Tour: We did this one – it was a small 2-4 person boat and we loved it! 

Recommended by Kelsea of Out of Office Mindset

• Boston Harbor
• Boston Harbor webcams

Sip Beer at the Sam Adams Brewery Tour

If you love beer, a visit to Samuel Adam’s Brewery is sure to be the highlight of your Boston trip! Not only can you take a tour of their brewhouse, they also offer a wide range of experiences to engage every beer lover out there whether you’re a beginner or bona fide brew master.

They’ve even got a fun tour for the foodies where you can sample their small batch, barrel-aged beers paired with local cheeses. For those wanting something a little extra special, Sam Adams even offers ongoing events like Taproom Trivia every Thursday, beer mixology classes, music bingo and even a speakeasy-style prohibition day celebration!

But, if you’re really looking to be dazzled, try Sam Adam’s VIP experience which takes you into the secret lab in their Nano Brewery where you’ll taste never-before-seen beer and witness the process it takes experiment and select Samuel Adams next superstar beer before it hits the shelves.  

And if you happen to come on one of their hoppiest times of year, St. Patrick’s Day, you’ll be treated to the festivities of all festivities, honoring this simple and classic past time. Cheers! 

Recommended by Geeves from Real Girl Review

• Samuel Adams Boston Brewery
• 30 Germania St, Boston, MA 02130
• 617-368-5080

Head to College for a Day at Harvard

Harvard University is one of the most prestigious Ivy League colleges in the United States. If you’ve ever dreamed of walking through the campus and seeing it first hand, now’s your chance.

Located right outside of Boston in Cambridge, Harvard University Visitor Center offers a free in-person Historical Tour of Harvard walking tour. This student led tour explores Harvard Yard – the oldest part of the university with some of the most historical points of interest on campus, including the John Harvard statue. However, you might want to think twice before rubbing his golden foot for good luck.

Tours depart from the visitor center which is located at the front desk in the Smith Campus Center and lasts about an hour. Advance registration is required.

In addition to the in-person tours, if you prefer to do a tour on your own, Harvard also has a free mobile app that offers a collection of different self-guided tours focused on the Harvard University experience. This one mile, self-guided tour takes place across fourteen mapped stops on campus and takes about an hour to complete.

• Harvard University Visitor Center
• 1350 Massachusetts Avenue, Cambridge, MA 02138.
• 617-495-1573

Eating Cannoli at Mike’s Pastry Shop is One of the Best Things to do in Boston

Visit the best Italian bakery in the North End of Boston. Established in 1946, this bakery has stood the test of time and become a can’t-miss place when visiting Boston for the first time. As you walk into the shop, you are greeted by the sights of gorgeous pastries in display cases and the laughter of people enjoying their treats.  

Locals and visitors alike will line up on Hanover Street just to purchase a freshly baked cannoli or lobster tail pastry. The lobster tail is the American version of the sfogliatelle ricce. They are a bit larger and filled with choux paste before baking. This causes the pastry to puff up in the oven, and the perfect space to fill a mixture of pastry cream and whipped cream.

For those who are visiting, it’s best to arrive at Mike’s Pastry Shop on foot due to the narrow streets and scarce parking spots. Visitors can exit from the Aquarium Station (Blue Line) or the Haymarket Station (Orange Line) on the MBTA. Mike’s Pastry is less than a minute’s walk from Paul Revere’s House. Other fantastic stops along the way include the Old North Church, The Paul Revere Statue, Faneuil Hall, and the New England Aquarium.

Recommended by Kate from Passports and Playgrounds

• Mike’s Pastry
• 300 Hanover St, Boston, MA 02113
• 617-742-3050

Sample Street Food on at Quincy Market

Quincy Market is one of the most beloved landmarks in Boston, and if you’re looking to get your fill of authentic Bostonian food this is the best place to visit! The market has been serving hungry guests since 1826. The market originally focused on selling fresh produce, but today it’s far more focused on serving up street food of different varieties and fun Boston souvenirs.

Since Quincy Market is on the Freedom Trail and near Faneuil Hall there’s no reason not to add it to your Boston itinerary! With over 50 food vendors to choose from, though, stepping inside Quincy Market can feel quite overwhelming if you don’t have a plan of action.

Top-rated stops at Quincy Market include the Boston and Maine Fish Company, where you’ll get insane hot buttered lobster rolls, and Regina Pizza, where you’ll find huge and delicious slices of pizza with a variety of toppings.

Quincy Market is open Monday-Saturday from 10am-9pm, and on Sundays from noon until 6pm. Entry is free!

Recommended by Ella from Many More Maps

• Quincy Market
• 206 S Market St, Boston, MA 02109
• 617-523-1300

See Works of Art at Isabella Stewart Gardner Museum

This unique museum is a must-see for any art, architecture, or history-lover while in Boston. Not only does it have an impressive collection of European, Asian, and American art, but it was designed in the style of a 15^th-century Venetian palace. And it was home to the biggest art heist in modern history.

Isabella Stewart Gardner was an art collector and patron of the arts. After her husband’s passing, she opened the museum to share her collection of paintings, sculptures, furniture, and rare books. Upon her death in 1924, Isabella left the museum for the education and enjoyment of the public forever. Since then, nothing in the galleries had been changed, until March 18, 1990.

That night, two men dressed as police officers tricked the security guards into letting them into the museum. They made off with thirteen works of art, including a Rembrandt and a Vermeer, that would be valued at $500 million today.

Despite hefty reward money, none of the stolen works have ever been recovered. When visiting, you can learn about the heist and see the empty frames that held the art. Plan to spend at least an hour at the museum, ideally two. After seeing the gallery, relax in the peaceful indoor courtyard or grab a bite at the museum’s café.

Fun Fact: Admission is free on your birthday or if your name is Isabella!

Recommended by Laura at Wine Travelista

• Isabella Stewart Gardner Museum
• 25 Evans Way, Boston, MA 02115
• 617-566-1401

Get Historical on the Famous Freedom Trail

If you’re looking for the best things to do in Boston on a weekend getaway in Boston, following the Freedom Trail will deliver you straight to many of them! Boston’s famous Freedom Trail knits together 16 historical attractions relevant to the American Revolution over the course of a 2.5 mile route through the city.

While two of the sites – the Bunker Hill Monument and the USS Constitution – are a bit of a hike from the rest of the attractions, the other 14 sites can be experienced more or less back-to-back.

Top attractions on the Freedom Trail include Old North Church, the Boston Common, the King’s Chapel and Burying Ground, Faneuil Hall, and more. Some stops (like the Paul Revere House) are museums you can go inside, while others (like the Boston Massacre Site) are merely points of interest.

You can easily experience the bulk of the Freedom Trail on one very full sightseeing day in Boston – on a self guided tour – but if you’re particularly interested in learning about 18th century American history, you may want to take a bit longer to explore!

Recommended by Kate from Our Escape Clause

Read a Book at the Boston Public Library

Visiting the Boston Public Library is one of the best things to do in Boston and one of the most outstanding libraries in the United States. According to the library’s website, among other things, the library “was the first large free municipal library in the United States and the first public library to lend books”. It’s a Boston historic cultural institution!

The library is also the second-largest public library in the U.S, right behind the Library of Congress. It’s so large, it contains approximately 19 million books and electronic resources. It also houses the personal 3,800 volume library of John Adams. You know – that John Adams – founding father and second president of the United States.

However, it’s not just the size that’s impressive but the Renaissance Revival architecture is quite beautiful as well. Designed by Charles McKim – a famous 19th century architect – the building was completed in 1895. The original building is a research library and an extension built later on in the 70’s serves as the general library.

A true “palace for the people” as it was described when it opened – besides books and literature, the library hosts special exhibitions, popular lectures and even concerts. Stop by Monday-Thursday 8am-8pm and 8am-5pm on Friday and Saturday. They are even open 11am-5pm on Sundays.

• Boston Public Library
• 700 Boylston Street, Boston, MA 02116
• 617-536-5400

Smell the Flowers at the Boston Public Garden

The Boston Public Garden is a must-visit for anyone visiting the city. It is the first public garden in the country, and one of Boston’s beloved green spaces.

Located in downtown Boston, adjacent to the Boston Common, the garden is home to many mature trees, lots of formal flower beds, and a pond with water birds such as ducks and geese.

Some of the top things to do in Boston Public Garden include admiring the equestrian statue of George Washington, going for a swan boat ride, and snapping a photo of the famous “Make Way for Ducklings” statue. There’s also an unusual monument called the Ether Monument that commemorates the first use of ether as an anesthetic.

The park’s flowers are beautiful in spring, summer, and fall. Thousands of tulips in the spring create a breathtaking display. In the fall, changing leaf colors make for a pleasant stroll.

Allow two to three hours. Bring a picnic and take a break from sightseeing in the tranquil garden!

Recommended by Dhara from It’s Not About the Miles

• Boston Public Garden
• 4 Charles St, Boston, MA 02116
• 617-635-4505

Stroll Through Beautiful Beacon Hill

Even if you’ve never been to Beacon Hill, you’ve for sure seen photos of this classic Boston neighborhood. Best know for it’s narrow streets, red brick homes and buildings, Beacon Hill is one of the must do things to do in Boston when you visit. This cozy part of the city is home to quite a few of Boston’s most popular landmarks and places to see.

One of the most famous streets in all of Beacon Hill is Acorn Street. With its narrow cobblestone pathway, lined with old historic brownstones, it gives the visitor a glimpse into old colonial Boston. If you happen to visit Boston in winter, this area is especially festive during the holidays when it’s decorated with Christmas lights and wreaths.

Be a Star For the Day on a Movie Tour

No article about things to do in Boston would be complete without including a little bit of info about the iconic phrase that’s become synonymous with Boston. You know the one I’m talking about.

Made famous back in 1997, in the popular movie Good Will Hunting, the phrase “wicked smart” is easily the two of the most common words associated with Boston. The movie, obviously set in Boston, was written by and stars Matt Damon and Ben Affleck.

The storyline, based on Damon’s character Will Hunting, is a self-taught genius who worked at MIT (Massachusetts Institute of Technology) as a janitor. Will anonymously solves a very complicated math equation and then one of the university professors (Robin Williams) tries to help him realize his potential in life.

The movie had everyone rooting for Will and people everywhere, outside of Boston, saying “wicket smaht”. Which, by the way, was uttered by Ben Affleck’s brother in real life, Casey. He also went on to do one of the funniest Saturday Night Live skits of all times about Boston.

If you are a Good Will Hunting fan or just a movie fan in general, one of the most fun things to do in Boston is a movie tour that includes visiting over thirty locations from the dozens of movies that have been filmed in Boston.

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Even More Things to do in Boston

Even though Boston is a pretty big city, (pop 650,000) it’s fairly easy to get around in and see and do things on your own. The Go City Boston pass is an economical way to sightsee your way around the city. Visitors can choose from over 40 different activities and venues no matter if you are in town for one, two, three, five and even seven consecutive days.

Alternatively, the Boston City Pass, includes entrance to the New England Aquarium and the Museum of Science plus a visit to two other venues from a list of available options. The pass is valid for nine days from the first date of use and is perfect for someone visiting on a weekend or long weekend.

Boston is such an exciting, fun destination to visit in the United States and there’s way more to do than what’s on this list. You could easily spend a week there and never run out of activities. So, the next time you are planning a vacation or a long weekend getaway, why not consider visiting Boston? You won’t be disappointed.

See you on the road!

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