The 10 Best Things to Do in Boston for First Timers

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Boston is known for its Revolutionary history, terrible regional accent (I’m from Massachusetts and say this with confidence), and Matt Damon. Some of the best things to do in Boston are related to those 3 things, most of them are not. Visiting Boston for the first time? These 10 things should be on your list.

PS: Don’t miss our full-length Boston bucket list.

Watch a Red Sox Game at Fenway Park

BOSTON, MA - JUN 20: Fenway Park at night on June 20, 2011 in Boston, MA. Fenway Park has served as the home ballpark of the Boston Red Sox baseball club since 1912, as the oldest Baseball stadium.

I grew up in Massachusetts, so when I think of Boston the first thing that comes to mind is baseball. 

Boston’s favorite boys of summer play in the historic Fenway Park. Built in 1912 it’s one of the oldest ballparks left in the United States and it a bit of a baseball mecca. When entering the park it’s a bit dark and dingy, but once you walk up the ramp the bright green of the Green Monster, the tall wall in left field, will take your breath away. At least it did for me the first time I saw it.

While the good seats aren’t cheap I usually find pretty good ones for around $35 (depending on the game). Once you’re in your seat grab a beer and a foot-long hot dog and you’re good to go!

Not in town the baseball season or can’t catch a game? Not a problem. Take a tour of Fenway Park instead. With many different kinds of tours offered you’re sure to get the full Red Sox experience. Times vary and tour reservations should be made in advance.

*Check out more fun tours of Boston here, including bike tours, movie & TV tours, food tours, and so much more!

Visit the Isabella Stewart Gardener Museum

By Sean Dungan – Isabella Stewart Gardner Museum, CC BY-SA 4.0, Link

By far the most underrated and best museum in all of Boston the Isabella Stewart Gardener Museum can’t be missed.

Isabella Stewart Gardener was an intelligent, wealthy rebel who marched to the beat of her own drum. She had a love of art and literature that shows in her collection now on display at the museum. When she died she endowed that her home located in Boston’s Back Bay be a place for “the education and enjoyment of the public forever.”

At the Isabella Stewart Gardener museum, you can view Isabella’s amazing collection of art and literature, view her gorgeous garden, listen to music, and participate in workshops.

The museum is also the site of the biggest art heist to ever take place in the world. In the early hours of March 18, 1990, 13 priceless works of art were stolen from within the Isabella Stewart Gardener Museum. A few of the stolen works of art include Rembrandt’s Christ in the Storm on the Sea of Galilee, Vermeer’s The Concert, and Flinck’s Landscape with an Obelisk.

As you walk around the museum look for the empty frames. They are still on display and always will be.

To this day there is a $10 million dollar reward for information that will lead to the recovery of these paintings.

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Explore the Grounds of the Boston Common and Public Garden

Boston Common is one of the most important historical sites in the entire city. Over the years, the Common has seen the gathering of militia, Civil War recruitment, victory gardens, and cows grazing. Historic figures to the likes of George Washington, General Lafayette, Dr. Martin Luther King, Jr., and Pope John Paul II have stepped foot on Boston Common. 

While the Common is and will always be a place for exercising free speech, it has morphed into an amazing public park. It plays host to events, gatherings, and concerts. With sports fields, large trees perfect for picnicking under, and the frog pond (that you can ice skate on in the winter) make Boston Common one of the must-see spots in the city.

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Adjacent to Boston Common is the Boston Public Garden. The first public botanical garden in America, the Boston Public Garden is full of flowers, trees, and paths to stroll. In the spring, tulips fill the garden beds, which is my personal favorite time to visit.

However, a visit to the Public Garden isn’t complete without a ride on the swan boats. These boats date back to 1870 when Robert Paget, whose descendants continue to operate the business today, was given a boat for hire license to row boats in the Boston Public Garden lagoon. The boats on the lagoon today date back to 1910 and sport a gorgeous wooden swan at the back of the boat.

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Boston Swan Boats in Boston Public Garden

Take a Walk Along the Rose Kennedy Greenway

The Rose Kennedy Greenway is a public park created when the “Big Dig” moved the highway going through the city of Boston underground freeing up prime space in the city. After years of planning the Greenway was born.

Winding through 1.5 miles of Boston the Roe Kennedy Greenway plays hosts to local art, numerous foundations, local flavors, and space for families to explore and relax. An afternoon spent walking along the Greenway is always a great idea.

A few highlights of the Greenway include:

  • The Greenway Carousel: This unique carousel has hand-carved animals from the air, sea, and land of Boston Harbor.
  • Food Trucks: Food Trucks on Food Trucks on Food Trucks. All week long you can find a plethora of local food.
  • Labyrinth Fountain: While there are plenty of fountains scattered across the Greenway the Labyrinth Fountain is calming and fun.
  • The Mural Wall: This epic wall is always changing. Artists are given the opportunity to dress this wall up with their unique flair. 
  • Trillium Garden on The Greenway: Boston’s first open-air beer garden serving up local beer and wine.

To help you explore the Rose Kennedy Greenway more check out this interactive map.

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Eat (and Drink) your Way Through History in Boston

The city of Boston has been in existence since 1630, and believe it or not there are a few restaurants left in Boston dating back to its early days. These historic restaurants are some of the must-visit restaurants in the city.

The oldest tavern in Boston is The Green Dragon Tavern. It first opened its doors in 1654 and is most famous for being the site where the Sons of Liberty planned the Boston Tea Party. Stop here for a pre-dinner drink, just like Paul Revere did during his famous “midnight ride.”

Next head over to the Ye Olde Oyster House for dinner. This famous Boston restaurant holds the title for the oldest restaurant in the United States. The oysters are fresh and the beer is always cold. 

After dinner, you’ll need Boston’s most famous dessert, the Boston cream pie. Parker’s Restaurant has the most delicious Boston cream pie in the city. This yummy pie is actually a sponge cake filled with creamy custard. No one really knows why its called a pie, but it’s delicious and you’ll love it!

While these are just a few of the best places to eat and drink in Boston there are plenty more to discover with food tours and pub crawls happening all over the city.

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Discover the Boston Museum of Science

If you love science museums you’re going to fall head over heels for the Boston Museum of Science. This is one of the best things to do in Boston with kids, but it’s also a fantastic activity for adults.

With amazing permanent exhibitions about space, natural science and history, dinosaurs, and the human body you can easily spend an entire day at the museum. There is also a planetarium, an omni theater, and a seasonally open butterfly garden. With rotating exhibits for both kids and adults, the whole family will have a blast.

No matter what you do while at the Boston Museum of Science make sure you get to the Lighting Show. Yes, you read that right, the Lighting Show. It’s bright, it’s loud, and they play the Ghostbusters theme song. 

Pro tip: If you get a Boston attractions card, such as the Go Boston Pass, you can save money on attractions like the Museum of Science!

Walk the Freedom Trail

The Freedom Trail is a 2.5 mile path you can walk around Boston to discover 16 different historical sites. The trail is marked with easy to follow red bricks with bronze circular markers reading “The Freedom Trail Boston.”

The 16 historical sites along the route are museums, burying grounds, meeting houses and more that tell the story of the American Revolution.

Some of the best stops along the Freedom Trail you can’t miss during your visit are:

  • Granary Burying Ground: The final resting place of some of the fathers of the American Revolution including John Hancock, Paul Revere, and Sam Adams.
  • Old Corner Bookstore: This build is Boston’s oldest commercial building.
  • Old State House: The oldest surviving public building in Boston and just steps from the site of the Boston Massacre.
  • Paul Revere House: Home of the famous patriot, craftsman, businessman and entrepreneur Paul Revere.
  • USS Constitution: The oldest commissioned warship afloat in the United States.

You can explore the Freedom Trail on your own or take a guided tour. There are several different kinds of tours including tours focused around African American Patriots and Revolutionary Women.

Not only is walking the Freedom Trail going to teach you about the city it’s a great introduction about getting around as well. It wanderings through so many of Boston’s hot spots and will help you to discover the city and a new and fun way.

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Explore the Islands of Boston Harbor

The Boston Harbor Islands are often overlooked by visitors. If you don’t jump on a ferry and explore the islands you will be missing out!

Your adventure begins when you board the Ferry. Leaving from Long Wharf, near the New England Aquarium, the ferry will give you amazing views of the city as you head out to the islands. Ferries run seasonally, make sure to check the schedule before your trip.

With 34 islands and peninsulas to explore the first problem you’ll have is deciding where to go. The National Park Service and Massachusetts State Parks work in conjunction with one another to manage and maintain the islands and their facilities. 

The National Park Service offers a lighthouse tour where you’ll be able to see 3 lighthouses up close, get the history, and enjoy sailing around the harbor.

Camping is offered on several of the islands. Georges, Lovells, Grape and Bumpkin Islands offer 33 amazing primitive camping spots. Peddocks island offers yurt camping. Be sure to make reservations well in advance for all campsites. They can be made up to 6 months in advance of your arrival.

Other opportunities to explore the outdoors include hiking, birding, kayaking, sailing, and yoga. These activities are offered on your own or through tours seasonally. 

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Visit Faneuil Hall and Quincy Market

Faneuil Hall is a historical site, shopping center, and entertainment area. A stop along the Freedom Trail, Faneuil Hall was completed in 1742 and has served as a marketplace, meeting house, and armory over the years.

For history, visit the Boston National Historical Park and head up to the meeting room and get the full history of the building and area. The Great Hall is located on the second floor and is open to the public.

All around Faneuil Hall a shopping center has popped up and houses stores selling art, apparel, and other goodies. See the full list here.

With the open-air promenade to walk on sunny days there are plenty of fun outdoor activities happening all the time. If you’re lucky you’ll get to see some amazing street performers – and not just any performers as only the best ones get through the audition process.

There are also fitness classes, children’s activities, dance nights, and more. Check the calendar for more details.

And don’t forget about the food! You wanna go where everybody knows your name? Head over the Cheers. Don’t know what you want to eat? Head over to Quincy Market’s Food Colonnade with over 30 different choices of delicious food from all over the world.

Eat the Best Cannoli in Boston

There are 2 places in Boston that say they have the best cannoli: Mike’s Pastry and Modern Pastry. This feud has been going on for years and will probably never end.

Modern Pastry opened in 1930 in the North End of Boston and has been family owned and operated ever since. Modern Pastry prides itself in making old-world Italian desserts. If you’re in town get in line early to get your delicious desserts.

16 years later Mike’s Pastry opened down the street, and the competition began. Their signature white box tied with blue string can be seen all over the neighborhood. If you want a cannoli get their early the line gets really long.

Both pastry shops are some of the top spots to get cannoli in Boston.

What did we miss? What is your favorite thing to do in Boston? A must-visit site for a first time visitor?

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