Best things to do in Massachusetts

Pacaso script in charcoal.
Pacaso’s Editorial Team
September 15, 2026
A photo of a luxury home in Massachusetts, alluding to the topic of places to visit in Massachusetts.
Key takeaways
Massachusetts packs Revolutionary War history, world-class museums, and some of the East Coast's best beaches into one state. Boston anchors the list with the Freedom Trail, Fenway Park, and the Museum of Fine Arts, while Salem, Concord, and Plymouth cover the state's colonial and literary history. Cape Cod, Nantucket, and Martha's Vineyard bring the coastal side, and the Berkshires round things out with art, music, and fall foliage. Each season has its own draw, from summer beach days to Salem's month-long Haunted Happenings in October and Boston's holiday tree lightings in December.
Massachusetts is a state built on contrasts: a Revolutionary War capital with a modern skyline, quiet coastal towns a short drive from big-city museums, and mountain foliage a couple of hours from the ocean. Whether you're walking the Freedom Trail, spending a week on Cape Cod, or timing a trip around Salem's October crowds, this guide breaks down the best things to do in Massachusetts by region and by season.

What are the best things to do in Boston?

Boston is the natural starting point for any Massachusetts trip, with most of its major sites within walking distance of each other downtown.
  • Freedom Trail: A 2.5-mile, self-guided walking route connecting 16 Revolutionary War sites, including Boston Common, Faneuil Hall, and the Paul Revere House. Free to walk, though some stops along the way charge admission.
  • Fenway Park: The oldest ballpark in Major League Baseball. Catch a Red Sox game or book a stadium tour to see the Green Monster up close. Ticket prices vary by game and seat location.
  • Museum of Fine Arts, Boston: One of the largest art museums in the country, with collections spanning ancient Egypt to contemporary work. Admission runs around $27 for adults, with free entry for children six and under.
  • New England Aquarium: A four-story Giant Ocean Tank, a penguin colony, and hands-on exhibits make this a strong pick for families. Adult admission runs roughly $33, with New England residents getting a discount.
  • Isabella Stewart Gardner Museum: A Venetian-style palace built to house Gardner's personal art collection, with a courtyard that stays in bloom year-round. Admission is around $20 for adults, free for anyone 18 and under.
  • Boston Tea Party Ships & Museum: An interactive reenactment of the 1773 Tea Party aboard restored ships, with costumed interpreters throughout. Tickets start around $35.
  • Faneuil Hall Marketplace: Historic market buildings turned shopping and dining hub, with street performers and a lively atmosphere that picks up further during the holiday season.
  • North End: Boston's Little Italy, packed with pasta, pizza, and cannoli shops along narrow historic streets. Free to explore, with dining and shopping prices varying by spot.

What are the best things to do in eastern Massachusetts beyond Boston?

A short drive from downtown Boston opens up some of the state's most distinctive history, from witch trials to Walden Pond.
  • Salem: Home to the Witch House, the only structure still standing with direct ties to the 1692 Salem Witch Trials, and The House of the Seven Gables, the setting for Nathaniel Hawthorne's novel of the same name. Salem is at its busiest during October's Haunted Happenings, covered in more detail below.
  • Concord: Sleepy Hollow Cemetery is the resting place of Henry David Thoreau, Ralph Waldo Emerson, and Nathaniel Hawthorne, set in a quiet, park-like landscape. Walden Pond, Thoreau's inspiration for his famous book, is a short drive away and open for swimming and hiking in warmer months.
  • Cambridge: Home to Harvard University, where visitors can walk Harvard Yard, tour the campus architecture, and explore several free museums. Cambridge pairs well with a Boston day trip, since it's just across the Charles River.
  • Plymouth: Plimoth Patuxet Museums recreates 17th-century English colonial life alongside the Wampanoag Homesite, offering perspectives from both cultures. Admission runs around $35 for adults.
  • Battleship Cove: In Fall River, this is the world's largest collection of historic naval ships, anchored by the WWII battleship USS Massachusetts. Admission is around $25 for adults.

What are the best things to do on Cape Cod, Nantucket and Martha's Vineyard?

Cape Cod and the islands are where Massachusetts' coastal reputation comes from, and they're also where Pacaso's Massachusetts portfolio is concentrated.
  • Cape Cod National Seashore: Forty miles of protected coastline running through six beaches, from salt marshes to dune-backed shores. Parking runs $15–$25 per vehicle in season. 
  • Chatham: Sitting at the elbow of Cape Cod, Chatham has a quieter, more residential feel than some of the Cape's busier towns, with Chatham Lighthouse Beach as a local favorite for wide sand and frequent seal sightings.
  • Martha's Vineyard: An island escape south of Cape Cod, with the towns of Edgartown, Oak Bluffs, and Vineyard Haven each offering a different pace, from upscale dining to gingerbread cottages.
  • Nantucket: Cobblestone streets, a well-preserved whaling history, and some of the more refined dining on the Cape and Islands. Prices here tend to run higher than the mainland given the island's limited inventory.
  • Provincetown: An artistic, inclusive community at the very tip of the Cape, with a lively harbor, galleries, and one of the busiest summer festival calendars in the region.
Chatham is also where Pacaso's current Massachusetts home is based. Fox Hill is an 11,000-square-foot, five-bedroom retreat on 2.74 acres overlooking Crow's Pond, with a private boat dock, pool, game room, home gym, and sauna. It's a five-minute drive from Chatham's beaches and downtown.
Sunroom water views at Fox Hill that show how Cape Cod homes often center daily life around light, shoreline scenery, and relaxed mornings.
Fox Hill's pool and patio showcase the indoor-outdoor living that defines high-end Cape Cod homes.
A bright sunroom with panoramic water views at Fox Hill, a Pacaso home in Chatham on Cape Cod.
If you're weighing which Cape Cod town fits your plans best, our guide to 16 must-visit Cape Cod towns breaks down the differences between Chatham, Falmouth, Provincetown, and more. 

What are the best things to do in central and western Massachusetts?

Away from the coast, central and western Massachusetts trade beaches for rolling hills, historic villages, and the Berkshires' arts scene.
  • Old Sturbridge Village: A living history museum recreating a 19th-century New England village, with blacksmiths, weavers, and farmers demonstrating period trades. Admission runs around $27 for adults.
  • Norman Rockwell Museum: In Stockbridge, this museum holds the largest collection of Rockwell's original paintings and illustrations, capturing everyday 20th-century American life. Admission is around $25 for adults.
  • The Berkshires: Home to Tanglewood, the Boston Symphony Orchestra's summer home and one of the best outdoor concert venues in the Northeast, plus some of the state's most reliable fall foliage.

What are the best summer attractions in Massachusetts?

Summer is peak season across most of the state, especially on the coast.
  • Cape Cod and the islands: Beach season runs roughly Memorial Day through Labor Day, with the warmest water in July and August. Expect the highest home prices and the biggest crowds during this window.
  • Tanglewood concerts: The Berkshires' outdoor summer concert season draws crowds for lawn seating under the stars, running from late June through early September.
  • Whale watching: Boston Harbor and Provincetown both run whale watching tours through the summer, with humpback whale sightings common off the coast.
  • Boston Harbor Islands: A short ferry ride from downtown Boston puts you on car-free islands with beaches, hiking trails, and Revolutionary-era forts.

What are the best fall activities in Massachusetts?

Fall brings foliage, harvest festivals, and Salem's biggest month of the year.
  • Salem Haunted Happenings: Salem's month-long Halloween celebration runs the full month of October, with a grand parade, artisan markets, ghost tours, and haunted attractions drawing hundreds of thousands of visitors. Plan for October crowds and book accommodations well ahead if visiting during the final week.
  • Berkshires foliage: Peak color typically hits western Massachusetts in early-to-mid October, a week or two ahead of the Boston area.
  • Apple and pumpkin picking: Orchards across central Massachusetts and the Pioneer Valley open for u-pick apples starting in September, running through late October.
  • Head of the Charles Regatta: The world's largest two-day rowing event takes over the Charles River in Boston each October, drawing crews and spectators from around the globe.

What are the best holiday events in Massachusetts?

Boston leans into the holidays each winter, with events running from late November through New Year's.
  • Boston Common tree lighting: The city's official tree lighting typically takes place in late November on Boston Common, with thousands of lights strung across the Common, Public Garden, and Commonwealth Avenue Mall.
  • Faneuil Hall tree lighting and Blink: Faneuil Hall Marketplace hosts its own tree lighting the same season, followed by nightly Blink light-and-music shows that run through the New Year.
  • Christopher Columbus Park trellis lighting: The North End waterfront park's canopy of blue lights typically stays lit from late November through mid-April, making it one of Boston's more romantic seasonal spots.
  • First Night Boston: Boston's New Year's Eve celebration includes fireworks over Boston Harbor and family-friendly events downtown.

What are some unique experiences in Massachusetts?

A few things to do in Massachusetts are hard to find anywhere else.
  • Boston Duck Tours: A land-and-water sightseeing tour aboard restored WWII amphibious vehicles, covering Boston's major sites before splashing into the Charles River.
  • Swan Boats on Boston Common: A slow, pedal-powered ride on the Public Garden lagoon that's been running since 1877.
  • Cranberry bog tours: Southeastern Massachusetts grows a large share of the country's cranberries, and several working bogs near Plymouth and Cape Cod open for harvest-season tours each fall.
  • The Witch House at Salem: The only structure in Salem with a direct, documented tie to the 1692 witch trials, once home to a judge who presided over the proceedings.
  • Nantucket lightship baskets: A uniquely Nantucket craft tradition, with working artisans and shops on the island still weaving the woven baskets by hand.

Own a piece of the Bay State with Pacaso

Massachusetts brings together Revolutionary history, coastal towns, and a genuine change of season in a way few states can match. Whether that means Fenway on a spring evening, a week on Cape Cod in August, or watching the Berkshires turn gold in October, it's the kind of place that rewards a return visit rather than a single trip.Pacaso allows buyers to purchase a share (1/8 to 1/2) of a fully managed home through a property-specific LLC, giving them a true real estate asset without the full cost of ownership. On Cape Cod, that currently includes Fox Hill in Chatham, a five-bedroom, 11,000-square-foot home on Crow's Pond with a private dock, pool, and space for the whole family, professionally designed and managed so it's ready every time you arrive.To see the full range of homes across the state, browse Pacaso's Massachusetts listings, or learn more about how Pacaso co-ownership works.

Things to do in Massachusetts FAQs

01: What is Massachusetts famous for?

Massachusetts is best known for its role in the American Revolution and colonial history, along with its concentration of top universities, coastal towns, and strong seasonal identity, from fall foliage to snowy winters.

02: What can you do in Massachusetts for free?

Walking the Freedom Trail, spending time on Boston Common, visiting many museums on free admission days, and strolling through towns like Salem or Newburyport all cost nothing beyond food or parking.

03: What are the top things to do in Massachusetts today for adults?

Boston's museum scene, a Fenway Park game, wine and dining in the North End, and a day trip to Salem or Cape Cod are all solid options for an adult-focused day or weekend, depending on the season.

04: What are good things to do near Massachusetts for a day trip?

Rhode Island's Newport mansions, coastal New Hampshire, and southern Maine are all within a two-hour drive of Boston and make easy day trips or weekend add-ons to a Massachusetts visit.

05: What are the top Massachusetts vacation destinations for a second home?

Cape Cod and Nantucket are the state's most established second-home markets, prized for their beaches, historic town centers, and proximity to Boston.

06: What are the most popular Massachusetts attractions?

Fenway Park, the Freedom Trail, the Museum of Fine Arts, and Cape Cod National Seashore consistently rank among the state's most-visited attractions.

07: When is the best time to visit Massachusetts?

Summer (June through August) is best for Cape Cod and the islands, early-to-mid October is peak foliage season, and late November through December brings Boston's holiday events. Spring and early fall offer milder weather and smaller crowds statewide.

08: What can I do in Massachusetts on a rainy day?

Boston's museums, including the Museum of Fine Arts and the Isabella Stewart Gardner Museum, plus Old Sturbridge Village's indoor demonstrations and Salem's indoor exhibits, all make solid rainy-day options.

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