Looking for a diverse New England escape rich in history, coastline, and charm? Head to Massachusetts! Walk the Freedom Trail in Boston, relax on Cape Cod beaches, or hike the Berkshires. Whether you’re a foodie, history buff, or outdoor explorer, Massachusetts delivers year-round adventures with classic New England character.

Massachusetts Highlights:

  • For History Buffs: Walk the Freedom Trail in Boston – Visit historic sites like Paul Revere’s House and Boston Common on a 2.5-mile walking tour.
  • For Beach Lovers: Relax on Cape Cod – Enjoy scenic beaches, bike trails, seafood shacks, and whale watching on the iconic peninsula.
  • For Art & Culture Fans: Explore the Berkshires – Tour museums, enjoy outdoor concerts at Tanglewood, or hike rolling forested hills.
  • For Families: Discover the New England Aquarium – Meet penguins, sea turtles, and more at this Boston waterfront favorite.
  • For College Town Vibes: Visit Cambridge and Harvard Square – Browse bookstores, see Harvard Yard, and enjoy lively restaurants and cafés.

Best Time to Visit Massachusetts

The best time to visit Massachusetts is in the spring (April–June) and fall (September–October). Enjoy blooming gardens or brilliant foliage, pleasant weather, and seasonal festivals without summer crowds. Summer is great for beach trips, while winter draws skiers to the Berkshires.

How to Get to Massachusetts

  • If you are traveling by car: Massachusetts is connected by I-90 (Mass Pike), I-95, and I-495. Boston is about 4 hours from New York City by car.
  • By Air: Boston Logan International Airport (BOS) is the largest hub, with regional options in Worcester, Martha’s Vineyard, and Nantucket.
  • By Train: Amtrak’s Northeast Corridor and Downeaster lines serve cities like Boston, Springfield, and Worcester. MBTA commuter rail connects to suburbs.

Where to Stay in Massachusetts

  • Recommended for Families: Cape Codder Resort & Spa (Hyannis) – Family-friendly resort with indoor water park and beach access.
  • For Couples: Mirbeau Inn & Spa (Plymouth) – Romantic retreat with a French-inspired spa and fine dining near historic attractions.
  • For a Boutique Stay: The Verb Hotel (Boston) – Hip music-themed hotel near Fenway Park and Back Bay.

Best Things to Do in Massachusetts

Norman Rockwell Museum


See iconic American art or admire charming sights on an easy cultural trip.

Norman Rockwell Museum

© Norman Rockwell Museum

This museum, founded in 1969 with the help of Molly and Norman Rockwell, houses the world’s largest and most significant collection of Rockwell’s work, featuring 998 original drawings and paintings. It covers the artist’s contributions to society, social commentary, and popular culture.

The artist spent the last 25 years of his life in Stockbridge and Rockwell’s original Stockbridge studio, which was moved to the new museum site, is now also home to the artist’s archives. The Norman Rockwell Museum gallery building was designed by Robert A. M. Stern.

9 Route 183, Stockbridge, MA 01262, Phone: 413-298-4100

Peabody Essex Museum


Explore global collections or discover unusual maritime stuff in Salem.

Peabody Essex Museum

© Peabody Essex Museum

Founded in 1799, the Peabody Essex Museum in Salem is a museum of international culture and art committed to connecting art to the world.

The museum’s mission is to celebrate cultural and artistic creativity by stewarding, collecting, and interpreting objects of art and culture.

It was among the first museums in the nation to collect art and culture from around the world.

Its current collections range from contemporary and historic American to Maritime, Asian, Oceanic, African, and Native American art and culture and it has an archival library as well as historic Chinese and American houses.

East India Square (161 Essex St), Salem, Massachusetts 01970, Phone: 978-745-9500

Old Sturbridge Village


Walk through historic homes or watch exciting reenactments with the kids.

Old Sturbridge Village

© Old Sturbridge Village

A trip to this village brings you to the doorstep of the Northeast’s biggest outdoor history museum and calls to mind the 1830s in a rural New England town setting.

Old Sturbridge Village visitors are invited to visit the over 40 authentic buildings, featuring meetinghouses, homes, a district school, bank, country store, working farm, various trade shops, and three water-powered mills, all found on over 200 attractive acres.

Guests can also get to know heritage breed farm animals and meet staff dressed in period costumes.

The village is a learning resource and a showcase of life in 19th century New England and invites all its visitors to explore its rich history.

1 Old Sturbridge Village Road, Sturbridge, MA 01566, Phone: 800-733-1830, Old Sturbridge Village Video

Hancock Shaker Village, Pittsfield


Visit preserved buildings or admire peaceful landscapes on a quiet retirement outing.

Hancock Shaker Village, Pittsfield

© Courtesy of sphraner - Fotolia.com

In the late 1780s, the Hancock Shaker Village got off the ground when about 100 Believers created a community on land donated by fellow Believers.

By the 1830s, the community peaked with 300+ Believers on more than 3,000 acres.

During the height of their growth and religiosity, these Shakers built barns, workshops, dwelling houses, and other buildings, thus creating a big, successful farm.

The 1826 Round Stone Barn became the center of a thriving dairy industry.

These people relished a peaceful and hard-working life, separate from “The World.” Eventually, forces prevented them from growing their community, and in 1959, when they were unable to remain true to the principles, they sold their property to a group that vowed to preserve their heritage.

1843 W. Housatonic St., Pittsfield, MA, Phone: 413-443-0188, Hancock Shaker Village Video

The Clark Art Institute


Savor world-class art or enjoy scenic grounds during your summer visit.

The Clark Art Institute

© The Clark Art Institute

The Clark Art Institute is one of the few institutions in the world with a two-fold purpose as a research center for higher education and an art museum.

Its collection features American and European sculpture, paintings, prints, photographs, drawings, and decorative arts from the Renaissance to the early 20th century.

The museum has a large concentration of French Impressionist and Academic paintings, British silver, oil sketches, drawings, and the work of American artists George Inness, John Singer Sargent, and Winslow Homer.

Originally based on the founding gift from Francine and Sterling and Clark, its collection has expanded through acquisitions as well as bequests and gifts.

225 South Street, Williamstown, Massachusetts 01267, Phone: 413-458-2303

The House of the Seven Gables, Salem


Tour literary history or explore spooky sights on a fall weekend.

The House of the Seven Gables, Salem

© The House of the Seven Gables

Caroline Emmerton, a philanthropist and preservationist, founded the present-day museum to assist immigrant families who were settling in Salem. Inspired by Jane Adam’s Hull House, she purchased what was the old Turner Mansion in 1908 and restored it to its original seven gables. Emmerton’s goal was to preserve the house for future generations, to provide educational opportunities for visitors, and to use the proceeds from the tours to fund her settlement programs.

So the Turner-Ingersoll Mansion, known popularly as the The House of the Seven Gables, has survived with many of its original period features from the 17th and 18th centuries intact.

Over the last century, the House of the Seven Gables has continued to focus on its founder’s mission of preservation, education, and community service.

115 Derby Street, Salem, Massachusetts 01970, Phone: 978-744-0991, The House of the Seven Gables Video

What to do if you are traveling with kids:

New Bedford Whaling Museum


Look at giant whale skeletons or discover family-friendly maritime attractions.

New Bedford Whaling Museum

© New Bedford Whaling Museum

The New Bedford Whaling Museum was founded in 1903 and has a strong relationship with the communities it serves, offering a library of logbooks, journals, prints, a scrimshaw collection, Japanese whaling literature and art, and marine paintings.

Its complete coverage of 19th and 20th century whaling technology makes it a renowned destination for research.

Visitors can see the Lagoda, the world’s largest model ship from 1916, and the museum displays complete skeletons of four species, including the blue whale.

18 Johnny Cake Hill, New Bedford, MA 02740, Phone: 508-997-0046

Activities and Attractions for Couples and Singles:

Fenway Park


Catch a game or explore baseball history on an exciting Boston trip.

Fenway Park

© Courtesy of viva la penler - Fotolia.com

Over generations, Fenway Park – home to the Boston Red Sox – has remained much as it was the day it opened on April 20, 1912.

Once spectators come to a game, they instantly see why the park is so beloved.

It is uniquely a part of the city of Boston itself and if you take a tour of the park you can see a place where traditions are celebrated, dreams are made, and baseball is forever.

Guests can see the home of Red Sox legends, observe Pesky's Pole firsthand, and sit on top of the so-called Green Monster that reaches more than 37 feet high and overlooks leftfield.

Well-informed tour guides offer a memorable one-hour walking tour of the park and other tours are available – including in Japanese and Spanish with advanced notice. All fans are welcome at Fenway Park, the pulse of the Red Sox Nation.

4 Yawkey Way, Boston, MA 02215

Boston Public Garden


Ride the swan boats or walk along romantic paths with your partner.

Boston Public Garden

© Courtesy of Zack Frank - Fotolia.com

Established in 1837, the Boston Public Garden was the country’s first public botanical garden. The Parks Department remains true to its Victorian traditions, so visitors can continue to admire unusual and rich plants, the fountains, the lagoon, the monuments, and the swan boats, which were created and have been operated by the Paget family for more than 100 years.

The Recreation Department and Boston Parks grow the plants used in the garden and more than 80 plant species are being cultivated for future planting in the garden and in over 50 locations throughout Boston.

4 Charles Street, Boston, MA 02116, Boston Public Garden Video

Tanglewood


Listen to live music or picnic on the lawn during a couples’ weekend.

Tanglewood

© Tanglewood

In 1934, certain Berkshire summer residents made arrangements for the New York Philharmonic to hold three outdoor concerts at Interlocken. In 1936, Serge Koussevitzky and the Boston Symphony Orchestra were invited and they accepted.

Mrs. Brooks and Miss Tappan offered Tanglewood, the Tappan family estate, as a gift to Koussevitzky and the orchestra. In August 1937, the festival's largest audience thus assembled for the first Tanglewood concert.

Today, Tanglewood draws more than 350,000 visitors annually and each season offers a vast spectrum of music.

297 West Street, Lenox, MA 01240, Phone: 888-266-1200

Where to Eat in Massachusetts

  • Recommended for Families: Legal Sea Foods (Multiple locations) – Consistently fresh seafood in a kid-friendly environment.
  • For Fine Dining: Mamma Maria (Boston – North End) – Elegant Italian fare in a historic townhouse near the waterfront.
  • For a Casual Bite: The Clam Shack (Falmouth or Ipswich) – Classic fried clams, lobster rolls, and chowder by the sea.

If you are interested in local events:

  • For Sports Fans: Boston Marathon (April) – Watch the world’s oldest marathon finish in Copley Square.
  • For History Fans: Patriots’ Day Reenactments (April) – Celebrate Revolutionary War heritage in Lexington and Concord.
  • For Art & Music Fans: Tanglewood Music Festival (Lenox) – Summer home of the Boston Symphony Orchestra in the Berkshires.

Day Trip Itineraries Within 30 Minutes of Boston, Massachusetts:

  • For Coastal Walks: Marblehead (30 min) – Stroll colonial streets and scenic harbor paths in this historic seaside town.
  • For History Buffs: Concord & Lexington (20–30 min) – Visit battlefields, authors’ homes, and Revolutionary War landmarks.
  • For Beach Days: Revere Beach (15–20 min) – America’s first public beach, ideal for a quick ocean getaway.
  • For Art & Gardens: deCordova Sculpture Park (Lincoln) (30 min) – Outdoor art installations and peaceful forested walking paths.
  • For Harbor Views: Boston Harbor Islands (30 min ferry) – Take a boat to Georges or Spectacle Island for hiking, picnicking, and views of the city skyline.

Frequently Asked Questions:

  • What makes Massachusetts a great family destination?
    • Massachusetts is known for its abundance of things to see and do with the whole family.
  • What are some must-visit places in Massachusetts?
    • Visit the famous Nantucket Island, Martha’s Vineyard, and Cape Cod which are like their own hidden worlds, complete with picturesque lighthouses and excellent beaches.
  • What else does Massachusetts offer to travelers?
    • Western Massachusetts offers stunning fall foliage and many unique museums. There’s also music at Springfield's Symphony Hall and hoops at the Basketball Hall of Fame.
  • Which college towns can be visited in Massachusetts?
    • Massachusetts has some of the world’s most idyllic college towns like Northampton and Amherst.

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