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Top 12 Things to do in Boston

Boston is an inviting and lively city that has centuries of history just waiting to be explored.

A perfect spot for sports aficionados, foodies, art and museum lovers, and beyond, New England’s biggest city has a number of advantages, and its location on the water makes it an ideal spot for all things maritime.

While there are tons of great things worth your time in Boston, look no further than a local’s guide to the top twelve things to do in Boston.

12 Awesome Things to do in Boston MA 

The Freedom Trail

Boston is known as the cradle of American independence, and its historical importance as one of the independence movement’s foundational places cannot be understated. The Boston Freedom Trail encompasses many of the most important historical sites, all along a 2.5 mile trail.

The trail is mostly flat, and clearly demarcated by a brick pathway, 2 bricks wide, which makes navigating easy. There are 16 stops in total, and you will pass through several iconic Boston neighborhoods on your way, such as Beacon Hill and the North End.

Some highlights of the Freedom Trail include the Paul Revere’s house, the site of the Boston Massacre, and the Old North Church– where Paul Revere hung the lanterns signifying the arrival of the British, “one if by land and two if by sea.”  The trail ends across the river in Charlestown, at the memorial to the Battle of Bunker Hill, fought there in 1775. Exploring the whole Freedom Trail is a must-do when you are in Boston, and it’s recommended to budget a half day or so for this activity– it is worth taking your time and completing in full! 

Copley Square

Boston’s most beautiful open square area, Copley Square is the place to relax and enjoy what the city has to offer.  Several famous buildings surround the square, and learning about their history is an absolute delight.

Copley Square is home to two of Boston’s most iconic churches, and though they are very different architecturally, each one has its charm. On the eastern side of the square is Trinity Church, a masterpiece of design– this is one of the most famous churches in the United States.  This building created a new style called the Richardsonian Romanesque, named after the architect, Henry Hobson Richardson.

The other church located at Copley is the Old South Church which is another architectural gem. The Boston Public Library is also found here at Copley Square, directly opposite Trinity Church. It is absolutely gorgeous on the inside, and one of the city’s most Instagrammable locations and best-kept secrets.

There’s a large open-air courtyard in the middle of the building, and the Bates Room on the second floor has the “vintage study decor” vibe down pat. Behind the Trinity Church, check out New England’s tallest building– the John Hancock building.

North End + Italian Food

Boston’s food capital, the North End is a bonafide mecca of Italian cuisine in the area.  Due to the number of Italian immigrants that moved to Boston, many of them to the North End, this part of the city is the best place to find top-tier Italian food. 

With so many great choices the problem is not if you will find a great meal… but rather narrowing down where you want to go.  Despite being a tourist hotspot, the North End still lives up to its reputation for great food and ambiance. 

Make sure to grab a cannoli at Mike’s Pastry or Modern Bakery to complete the ultimate North End experience– the “cannoli war” between the two establishments is legendary! Some restaurants to consider are Giacomo’s for fresh pasta (keep in mind they have a tiny seating area and don’t take reservations!); Monica’s for squid ink pasta; and Antico Forno for lasagna. Of course, the quintessential pizza experience can be had at Regina’s. 

Whale Watching

One of the lesser-known activities you can partake in while in Boston is whale watching.  After a quick ride out from the Boston Harbor to the Stelwagon Bank, you’ll be able to see the whales up close and personal. While this may seem overly touristy, it’s actually a fantastic experience.

You will be in total awe of how big some of these humpback whales are, and how close they get to the boat! The tour leader will also give you some information on the whales here and their habitat, and the views of the Harbor, the skyline, and the vast ocean are top-notch.

Fenway Park

Possibly the most iconic baseball stadium in the country, Fenway is a must see for those visiting Boston.  If you are in town when the Red Sox are playing, it’s worth the splurge to attend a game. The energy is crackling, the seats are close together, and the fans are electric.

There are also tours offered for checking out the park if there isn’t a game on, so you can still walk around the stadium where so many of baseball’s greats have played. The Fenway neighborhood has recently been largely renovated, with big skyscrapers, classy cuisine, and nice areas to walk around, especially on summer evenings. 

The Charles River Esplanade

Following along the Charles River, the Esplanade is a series of parks that will be sure to impress. The three miles that make up the Esplanade contains many beautiful bridges, playgrounds, docks and beer gardens, all with river views of the magnificent Charles River.

While great all year round, the Esplanade is at its best in the spring and summer, when the flowers are blooming and the trees are green and full. There are lots of places to sit and relax  by the water and enjoy the sunset. 

This is extra special when you bring a picnic as the time just seems to fly by, or you can check out seasonal biergartens and pop-ups along the banks. The Esplanade is also ideal for riding a bike, due to its long and flat nature and it’s paved bike paths. You can explore both the Boston and Cambridge side of the Esplanade, and it’s a beautiful way to spend a sunny afternoon in any season.

The MFA + the Isabella Stuart Gardner

Boston is home to many great museums, but none of them top the Museum of Fine Arts.  This huge museum is home to many wonderful exhibits, including some of the best Impressionist pieces found in the US. 

You can easily spend a whole afternoon wandering through the halls of the MFA, reading about each piece of art– and you will not have had enough time to see everything!  The Egyptian section is also an absolute highlight, as there are tons of artifacts on display that offer a detailed look into ancient Egypt. 

Even if you feel like you have been to tons of art museums before and you have seen it all, the MFA still has lots to offer anyone interested in art or history.  Well worth a visit while you are in Boston for your dose of culture! Nearby is the smaller Isabella Stuart Gardner, a gallery donated by a Bostonian, Isabella Stuart Gardner, which she left to the city in her will. The scene of a famous, still-unsolved art heist in the 1990s, the ISG is a great option for those who perhaps don’t have time to do the MFA but still wish to visit a museum while they’re in town.

Shopping in Back Bay

Boston’s premiere shopping area, Back Bay is filled with boutiques, whether for some retail therapy or for window-shopping. The main street is Newbury Street, which is where you will find many high-end stores, but the street itself is lovely and eye-catching just to stroll up and down. 

If you want to go into a proper shopping mall, the Prudential Center is what you are looking for. Often called “The Pru,” the Prudential has a skydeck, a huge Italian market called Eataly, and is a sleek and shiny addition to the city.

One block over from Newbury Street is the Commonwealth Avenue Mall, a gorgeous promenade surrounded by beautiful apartment buildings– truly the creme-de-la-creme of Boston society. The end of the Commonwealth Avenue Mall connects to the beginning of the Public Garden.

Boston Common and the Public Garden

There are many beautiful parks in the city, but the Boston Common and the Public Garden may be the top two. The Common is the oldest city park in the country, founded in 1634. Strolling down the many wide paths is a dream and you can even watch a Shakespeare performance here in the summer.  The Public Garden in spring is filled with color and life as the many flowers bloom and show their brilliance. 

Take a little boat ride in the Public Garden on the famous Swan Boats, and afterwards visit the Make Way for Ducklings statues.

These cute sculptures are often dressed up in festive garb depending on the season. Visiting these well maintained parks in the heart of Boston is definitely a must– they’re a green oasis smack-dab in the middle of the city.

Beacon Hill

Boston’s most quaint neighborhood, walking around Beacon Hill is like stepping back in time.  Tree-lined streets and old row houses make up this historic area, with charming cobblestoned streets and old-style storefronts. While you are walking through this part of town, be sure to check out the top tourist spots like the recreation of the bar from the sitcom Cheers, Acorn Street, and Louisburg Square.

Acorn Street is often considered “The Most Photographed Street in America,” so be sure to get there early for good photos. Around Beacon Hill you can also the Black Heritage Trail, which stops at several sites important to Black history in the Beacon Hill neighborhood.

Must-see sites include: the 1806 African Meeting House (the oldest Black church in the country); the Abiel Smith School, now the Museum of African American History; and the Lewis and Harriet Hayden House, a stop on the Underground Railroad.

Visit a Boston Brewery

Boston is a very proud beer city, and with several excellent breweries founded here it is easy to see why Bostonians are such beer lovers.  The most famous brewery is probably Sam Adams. With its classic Boston Lager, this brewery has forever changed the beer industry. You can tour their Boston location and taste several of their beers for free at the end of the tour, which is a really fun way to spend an afternoon. Another great area brewery is Harpoon, which is located in the Seaport district.

There are several long tables inside that are great for groups while enjoying a beer and pretzel (which are absolutely mouthwatering, made from their leftover yeast!) One of the top rated breweries in the country is also found in Boston, Trillium. Trillium specializes in farmhouse beers and hazy New England IPAs. Their beers have won many well-deserved awards. Their Fort Point brewery has a cool environment, but if you visit in the summer their outdoor beer garden at the Greenway is the best place to have a beer and socialize outdoors.

The Seaport

Boston’s newest neighborhood, the Seaport is a modern micro-city inside of Boston. With glittering skyscrapers and trendy shopping, it is clear why so many people flock to this area. This sleek architecture is so unlike the rest of Boston that sometimes you feel like you are in a totally different city altogether! However, Seaport has some of the best bars and restaurants around, from upscale dining to low-key lobster rolls at Yankee Lobster. 

All told, Boston is a city filled with activities for any age, budget, or interest. While its history is what makes it truly special, Boston is a lively and modern city that you will love getting the chance to explore for a few days.

Tegan George & Alex McKenzie from Why Not Walk

Tegan and Alex are travel, hiking, and biking enthusiasts currently based in Boston, USA, looking forward to moving to The Netherlands in 2021. There is nothing they love more than exploring new places by walking, and they have visited over 30 countries together since they met in 2015. Their love for “walking the world” led them to found Why Not Walk, a travel guides site. Follow them on Instagram, Facebook, or Pinterest to start planning your next adventure.

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