101 Things to Do in Massachusetts

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Massachusetts blends the living history of Boston and Plymouth with the beaches of Cape Cod, the islands of Martha's Vineyard and Nantucket, and the arts-filled Berkshires. Browse and book top experiences below, or request free quotes and let a local specialist plan your trip.

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Welcome to 101 Things to Do in Massachusetts. Click any activity below to search and book every tour, attraction and experience in Massachusetts.

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Popular Attractions & Tourist Sites in Massachusetts

1. Freedom Trail — A 2.5-mile red-brick walking route through Boston linking 16 Revolutionary War sites, from Boston Common to the USS Constitution.

2. Fenway Park — America's oldest active Major League ballpark, opened in 1912 and home of the Boston Red Sox and the Green Monster.

3. Cape Cod National Seashore — Forty miles of protected Atlantic beaches, dunes and lighthouses along the Cape's outer shore.

4. Salem — The historic seaport famed for the 1692 witch trials, with museums, the Witch House and a lively October season.

5. Martha's Vineyard — An island retreat reached by ferry, known for gingerbread cottages, cliffs at Aquinnah and classic New England beaches.

6. Plymouth Rock & Plimoth Patuxet — The landing site of the 1620 Pilgrims plus a living-history museum recreating the colonial and Wampanoag settlement.

7. Museum of Fine Arts, Boston — One of the largest art museums in the U.S., holding nearly 500,000 works across ancient to contemporary collections.

8. The Berkshires — A western Massachusetts region of rolling hills, Tanglewood's summer concerts and the MASS MoCA contemporary art complex.

9. Nantucket — A cobblestoned former whaling island with grey-shingled cottages, historic lighthouses and pristine beaches.

10. Boston Harbor whale watch cruises — High-speed catamaran trips to Stellwagen Bank to see humpback, finback and minke whales.

Unique Massachusetts Experiences

Walk the Freedom Trail with a costumed guide
Catch a Red Sox game at Fenway Park
Whale watch on Stellwagen Bank
Explore Salem's witch-trial history
Ferry to Martha's Vineyard for the day
Cycle the Cape Cod Rail Trail
Kayak the salt marshes of the Outer Cape
Tour Harvard and MIT in Cambridge
Hear a summer concert at Tanglewood
Sample chowder along Boston's waterfront

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Massachusetts Travel — Frequently Asked Questions

What are the top things to do in Massachusetts?

Top experiences include Freedom Trail, Fenway Park, Cape Cod National Seashore. You can browse and book hundreds more Massachusetts tours, attractions and activities — many at up to 50% off — right on this page.

How much can I save on Massachusetts tours and attractions?

Smart Traveler travelers save up to 50% on Massachusetts attractions, tours and activities through exclusive industry rates and long-standing partnerships.

When is the best time to visit Massachusetts?

Late spring through early fall (May to October) is ideal, with warm beach weather in summer and brilliant foliage in the Berkshires during late September and October.

Can a travel specialist plan my whole Massachusetts trip?

Yes. Beyond activities, our Massachusetts travel specialists arrange flights, hotels, cruises and complete packages. Request up to 5 free, no-obligation quotes and compare.