22 Essential Massachusetts Bucket List Activities & Food


Massachusetts may already be at the top of your travel bucket list – especially if you are interested in U.S. History. Here are some places to visit in and around Boston as well as the rest of the state.

Jump ahead to these sections:

Besides giving you ideas of what to do during the warm and cold months, we will also give you a brief list of food and restaurants you need to try while visiting. 

Massachusetts residents – let us know what we have left off our list!

Massachusetts Bucket List Trip Destinations

The good thing about traveling to Massachusetts is that the state is geographically small. The length of the state is 190 miles, and the northern and southern borders are only 50 miles apart. 

Even if you plan to visit some of Boston’s sites, consider renting a car to venture out of the metropolitan area. Visit the historical villages surrounding Boston as well as the beautiful natural places. 

» MORE: Are you expecting a loss soon? Become a member for personalized support.

1. Boston Tea Party Ships and Museum 

We hate to use the word “museum” to describe this experience, as the word conjures images of glass cases full of artifacts and a lot of reading. The Boston Tea Party Ship and Museum does have a few artifacts, but people flock to this attraction to hear the historical reenactors describe the events that led to this famous moment in history. 

You’ll even get to participate in the tea party by throwing a crate of tea off the ship.

2. Plimoth Patuxet

Your earliest history lesson probably had something to do with the Pilgrims and Plymouth Rock. So while you are in Massachusetts, take the time to visit Plimoth Patuxet, a living history museum that celebrates both the English Pilgrims and the indigenous people who lived in the area. 

The Mayflower II is located two miles from this attraction and is listed on the National Register of Historic Places.

3. Plymouth Rock

Plymouth Rock is located in Pilgrim Memorial State Park, which is located on the shore of Plymouth Harbor. The rock is said to mark the spot where the Mayflower landed in 1623, even though there is little historical proof that this was the exact spot. 

4. Harvard University

Apologies go to all Ivy Leaguers who didn’t attend Harvard, but for the rest of us, Harvard University represents the iconic American educational institution. While you can certainly wander the grounds (that are smaller than you would think), we recommend that you take a guided tour. Not only will the students giving the tour tell you a few stories from the university’s long history, but they will also tell you what it’s like to be a current student.

Outdoor Activity, Hike, and Adventure Bucket List Ideas for Massachusetts

Perhaps history isn’t your thing. Maybe you would rather visit the beautiful landscape of Massachusetts. Whether you are into beautiful coasts, thick forests, or fall leaves, there’s something for everyone in this state.

5. Whale watching tours

There are a lot of whale-watching tours scattered along the coastline of Massachusetts. The best time for whale watching is the warm months – from May to October.

6. Fall foliage

During October, people flock to the northeast to get views of the beautiful fall foliage. Tons of online recommendations highlight the best routes, but you may want to concentrate on those along a body of water. Search online for fall foliage or leaf-peeping routes.

7. Cemetery tours

While some of you may shudder at the idea of visiting a cemetery on vacations, others of you will travel to Massachusetts with the sole purpose of seeing some of the most famous cemeteries in the U.S.

The Puritan cemeteries in downtown Boston are hard to miss, but you also might want to visit the Mount Auburn Cemetery located between Cambridge and Watertown. Mount Auburn Cemetery is considered one of the first rural cemeteries and a popular gathering place during the 1830s. 

Spring and Summer Massachusetts Bucket List Ideas

Spring and summer are the best times to visit Massachusetts unless you are going to participate in winter sports. Here are some outdoor activities to enjoy during the warm months.

» MORE: Honoring your loved one doesn't have to be expensive. Sign up for free savings.

8. Nantucket Island

See how the 1% live by visiting Nantucket Island. This island has the highest concentration of pre-Civil War homes and a beautiful coastline. The area boasts some of the highest property values in the U.S., so don’t expect this to be a cheap place to visit. 

9. Freedom Trail tour

The Freedom Trail is a walkable path that guides you along Boston’s most historic sites. We recommend paying for a tour to get more out of the experience. You’ll visit meeting houses, churches, museums, and cemeteries along the route while led by a costumed historian.

10. Watch a game at Fenway Park

Fenway Park is the oldest and smallest ballpark in the Major League, making it a common addition on a sports-lover’s bucket list. But, even if you can’t score tickets for a Red Sox game, you can take a guided tour of this iconic ballpark. 

11. Take a Salem ghost tour

The village of Salem has a unique feel as it is undoubtedly most famous for the witch trials that occurred there in the late 1600s. As a result, there are a lot of cemetery and ghost tours in the town. In addition, you’ll see the Hocus Pocus house, as well as other locations known for hauntings and strange occurrences. 

Fall and Winter Massachusetts Bucket List Ideas

Pack layers if you are traveling to Massachusetts in late fall or winter. Here are some fall and winter activities to enjoy. 

12. Ice skating

Spend an hour or two ice skating at Boston Frog Pond or another spot in the state. Make reservations if you are headed to one of the more popular skating destinations.

13. Stay at a bed and breakfast

Winter is a great time to visit some of the historic villages surrounding Boston. Consider staying at a bed and breakfast in one of these villages to get a feel for the local community. 

Bucket List Foods and Restaurants in Massachusetts

Boston is a foodie’s paradise. While there are undoubtedly current hot spots on your food bucket list, there are also old standards to enjoy while visiting Boston. Here are some foods to enjoy while visiting the area. 

14. Union Oyster House

Whenever you try to label a location as the “oldest,” there are sure to be people who argue the fact. However, Union Oyster House is said to be the oldest restaurant in Boston. Regardless of its age, the restaurant is known for its oyster bar, lobster, and the Kennedy Booth (where the Kennedy family often sat while visiting the restaurant). 

15. Lobster roll

The lobster rolls in Massachusetts are generally served warm (unlike the lobster rolls in Maine). Every restaurant in Massachusetts claims theirs is the best.

16. Little Italy

The North End of Boston is known as Little Italy. There you’ll find Italian markets, restaurants, and bakeries. We recommend taking a food tour of the area if you have limited time in the city. And don’t forget to try the cannolis. 

17. Beer

As far as beer is concerned, Boston is probably most known for Samuel Adams Boston Lager. Undoubtedly, many other breweries are trying to reach such an iconic status.

18. Boston cream pie

A Boston cream pie has layers of pastry divided by custard. The top is glazed in chocolate. It is said to have been invented at the Omni Parker House in Boston.

Boston, Massachusetts Bucket List Ideas

We have already highlighted many Boston activities on our list. Here are a few more. 

Keep in mind that driving in Boston takes exceptional finesse. The traffic is horrible, even compared to other larger metropolitan areas. In addition, the curving highways, constant tunnels, and lack of grid system make it challenging to navigate. 

The good news is that Boston is a walkable city. Here are some of the top attractions in Massachusetts. 

19. Swan boat

As you stroll through the Public Garden in Boston, you are sure to see a fleet of pontoon boats shaped like swans. These boats have been part of the Boston scenery since 1877. However, they only run from April to September. 

If you are traveling to Boston with kids, make sure you read Make Way for Ducklings by Robert McCloskey before you go. The swan boats are featured in the story, and there is a nearby statue celebrating the book near the waterfront. 

If you visit the Public Gardens on a fine day, consider packing a picnic lunch and strolling through the surrounding neighborhoods.

20. Cheers bar

Fans of the 1980s sitcom will surely want to get their photo taken outside of the Cheers bar, located near the Public Gardens. The inside looks nothing like the TV bar, but it contains photographs and memorabilia from the show.

21. U.S.S. Constitution Museum

This iconic ship is part of the Freedom Trail sites and is a must-do when visiting Boston. The ship was most noted for her contributions during the War of 1812 and is nicknamed “Old Ironsides.”

22. Faneuil Hall 

Faneuil Hall is not only a historic site, but it also has shops, restaurants, and an open plaza where street performers gather. It was built in 1742 as merchant Peter Faneuil’s gift to the city. 

What Did We Leave Off Our List?

There is so much to see and do in Massachusetts that we are sure we inadvertently left a must-do attraction off our bucket list. 

Regardless, we hope that we got you started thinking about your own bucket list. What do you want to see and do before your time on earth ends? Consider creating a bucket list with easily achievable activities and those that push you a bit out of your comfort zone. 


Icons sourced from FlatIcon.