Skip to main content
Try our new AI Powered Travel Planner
It's Free. Try it now!

Massachusetts is a lot of personality packed into a small state. Boston, the home of Harvard, MIT, the Boston Tea Party, and the Red Sox, is a large part of the draw, but there is so much more to the state. Its rich history and strong culture make it a great place for sightseeing. With a little bit of everything, let’s take a look at these top Massachusetts bucket list things to do!

10. Taquería Jalisco

Taquería Jalisco


Taquería Jalisco is a must-visit on any Massachusetts bucket list. For nearly 25 years, this beloved Boston gem has delighted locals with its authentic Mexican cuisine. Indulge in flavorful pozole, succulent carnitas tacos, and spicy pork tamales, all complemented by delicious rice and refried beans. Don’t forget to top it off with a refreshing fruit juice, like pineapple or tamarind. Taquería Jalisco is a culinary treasure that captures the heart of Boston’s food scene.

9. Shopping On Newbury Street

Shopping on Newbury Street


What isn’t there to do on Newberry Street? The shopping here is truly out of this world, from trendy boutiques to huge international brands like Gucci and Saint Laurent. There are also some delicious places to grab a bite to eat while you’re doing a little shopping.

8. Wormtown Brewery

Wormtown Brewery(image via Facebook)


Benjamin Franklin once said, “Beer is proof that God loves us and wants us to be happy.” How better to honor that sentiment than at a locally-owned New England brewery? Wormtown is all about locally sourced ingredients, partnerships with local restaurants, and, above all, taking the greatest care with the freshest materials to produce the best beer. The tap room’s open from noon to nine if you want to stop in for lunch on your way out to Springfield for our next bucket list item.

7. Naismith Memorial Basketball Hall of Fame

Naismith Memorial Basketball Hall of Fame(image via Wikimedia)


Named for James Naismith, the Canadian doctor who created the sport, the Basketball Hall of Fame has been around since 1959, counting 345 players among its honorees. While it’s moved a couple of times, it’s always been in Springfield, where the sport was born. Sitting on the banks of the Connecticut River, the Hall has more than 40,000 square feet of space dedicated to the history of the sport and hosts skill challenges, clinics, shooting contests, and more.

6. Whaling Museum

Whaling Museum(image via Flickr)


Originally a candle factory, this museum has an enormous collection of artifacts, memorabilia, and information about the history of whaling. Here, you’ll find engraved bones, longboats, and the skeleton of a 46-foot sperm whale. There’s even a beam press, which was used to get oil from the whales to make candles. Of course, apart from aboriginal subsistence whaling, hunting whales is banned in the United States, so this is a fascinating look into a bygone industry.

5. Norman Rockwell Museum

Norman Rockwell Museum(image via Flickr)


Located in Stockbridge, Massachusetts, where Norman Rockwell spent the last 25 years of his life, the Norman Rockwell Museum is the largest collection of his original work in the world. In addition to the 574 pieces on display, there’s also an archive with over 100,000 items—photographs, fan mail, process drawings, and more. It’s a must-see for Rockwell fans, Americana enthusiasts, or anyone interested in the power of art to influence social attitudes.

4. Cottage Tour of Martha’s Vineyard

Cottage Tour of Martha’s Vineyard(image via Flickr)

Oak Bluffs

Every summer, the Martha’s Vineyard Camp Meeting Association hosts tours of the campgrounds and cottages. Originally started as a set of tents for religious camp meetings, the little campsite grew to some 312 cottages, which now occupy the area. People still live in them, actually, so if you want to see the inside, you’ll have to wait for the Annual Gingerbread Cottage Tour. Otherwise, regular campground tours happen twice a week in July and August.

3. Salem Witch Trials Memorial

Salem Witch Trials Memorial(image via Flickr)


The Salem Witch Trials Memorial is a tasteful tribute to the 20 people who lost their lives in the proto-McCarthy fervor. The monument was dedicated by Elie Wiesel and is an oasis of respect and reflection in the midst of a weird, weird town.

2. Plymouth Rock and Mayflower II

Plymouth Rock and Mayflower II(image via Flickr)


Plymouth is the epicenter of United States history. This is where the Mayflower, the ship that carried the Pilgrims to the New World, landed. They left from Plymouth, England, so they must’ve been homesick or out of ideas for names by the time they landed. Plymouth holds a full-scale replica of the original Mayflower, and seeing the ship’s small size gives a tangible sense of the hardship those 102 people faced during the 10-week voyage.

1. Cambridge Center Roof Garden

Cambridge Center Roof Garden(image via Flickr)


No Massachusetts bucket list is complete without a visit to this last location. This literal secret garden sits on top of a parking garage that belongs to the Marriott Hotel in Kendall Square. For people in the know, it’s a great place to bring a lunch and enjoy the quiet tranquility. Or, if you’re a tourist, it’s a great place to get a unique view of the city.



Related Reads