Massachusetts · best-of list
10 Top Things to Do in Massachusetts
All 10 things to do our route editors picked in Massachusetts, across 3 destinations, gathered in one list. Each one is a stop on a route you can open and copy into a trip.
Our curated picks
10 things to do in Massachusetts, grouped by destination. Destinations with the most picks come first; this is not a ranking.
Boston 4 picks
Fenway Park
Boston · On our Boston to Portland route
Baseball's oldest ballpark (1912); take a tour or catch a game.
Tip: Ballpark tours run year-round.
Photo: Rick Berry · Public domain
Freedom Trail
Boston · On our Boston to Portland route
2.5-mile red-brick line past 16 Revolutionary-era sites.
Tip: Start at Boston Common and finish in Charlestown.
Photo: Ingfbruno · CC BY-SA 3.0
Isabella Stewart Gardner Museum
Boston · On our Boston to Portland route
Art collection displayed around a Venetian-style courtyard.
Tip: Free if your name is Isabella.
Photo: Federal Bureau of Investigation · Public domain
Museum of Fine Arts, Boston
Boston · On our Boston to Portland route
Encyclopedic art museum with strong American and Impressionist galleries.
Photo: ajay_suresh · CC BY 4.0
Downtown Boston & the Waterfront 3 picks
Boston Common
Downtown Boston & the Waterfront · On our Boston New Year's Eve route
The country's oldest public park, with the Frog Pond rink, where the First Night parade ends and fireworks go up at 7 p.m.
Tip: Skate at the Frog Pond on Dec 30; on First Night 2025 the Skating Club of Boston performed there at 3 and 5:30 p.m.
Photo: Daderot · CC0
First Night Boston
Downtown Boston & the Waterfront · On our Boston New Year's Eve route
Free citywide New Year's Eve festival for 50 years, centered on City Hall Plaza with ice sculptures, music and food.
Tip: The ice sculptures look best just after dark, before the 6 p.m. parade gathers.
Photo: Daniel Schwen · CC BY-SA 4.0Long Wharf
Downtown Boston & the Waterfront · On our Boston New Year's Eve route
Historic wharf on the downtown waterfront and the main viewing point for the midnight fireworks over the harbor.
Tip: The end of the wharf fills by 11:30 p.m.; the Harborwalk to the north has more room.
South Boston & Castle Island 3 picks
Castle Island
South Boston & Castle Island · On our Boston New Year's Eve route
Harbor-mouth park around Fort Independence, a granite fort of the 1830s, joined to South Boston by a causeway.
Tip: Planes from Logan pass low overhead; the fort's walls block the wind on the harbor side.
Dorchester Heights
South Boston & Castle Island · On our Boston New Year's Eve route
Hilltop monument where Washington's cannon forced the British out of Boston in March 1776.
L Street Brownies New Year's Day Plunge
South Boston & Castle Island · On our Boston New Year's Eve route
South Boston's swim club has run into the harbor every Jan 1 since 1904, with about 500 swimmers in 2026.
Tip: Plunging is for club members; watch from the beach by the Curley Community Center.
How we picked these
Every entry is a stop on at least one of TripsCircle's hand-curated routes, chosen by our route editors, who wrote the reason to go shown with each place. These are our curated picks, not a scored ranking: we haven't rated or reviewed them against each other. The list is grouped by destination, and within each destination places that appear on more routes come first.
Prices ($ to $$$$) and visit lengths are rough guides from our route notes, not quotes. Check opening hours before you go.
About this list
How did you choose the things to do in Massachusetts?
Each one is a stop on a TripsCircle route that our editors built by hand, and each comes with a written reason to go. This page shows all 10 of them. They are curated picks, not a ranked score.
Which part of Massachusetts has the most things to do on this list?
Boston has the most (4 of 10), followed by Downtown Boston & the Waterfront (3) and South Boston & Castle Island (3).
Are any of these free?
7 picks on this list are marked free in our route notes: Boston Common, Castle Island, Freedom Trail, First Night Boston, L Street Brownies New Year's Day Plunge, and more. Check ahead, since parking or special exhibits can cost extra.
More lists for Massachusetts
Top things to do nearby
Destinations on this list
- Boston 4 on this list
- Downtown Boston & the Waterfront 3 on this list
- South Boston & Castle Island 3 on this list
Turn this list into a plan
Open a curated route in TripsCircle, add the spots your crew wants, vote with polls and keep everyone on one shared itinerary.