Overview
Massachusetts is a quirky, coastal New England state that’s equal parts revolutionary history and modern charm. From Boston’s bustling streets to Martha’s Vineyard’s laid-back beaches, there’s a slice of Massachusetts for everyone. Think vibrant autumn foliage, clam chowder that’ll make you weep tears of joy, and enough culture to fill Fenway Park—twice.
Best Time to Visit Massachusetts
Boston & Eastern Massachusetts:
Best time: Late spring (May-June) and early fall (September-October). Although hotter summer is my preferred time to visit (Late June-End of August).
Why: Blooming gardens in spring; crisp air, vibrant foliage, and Red Sox games in fall.
Cape Cod & Islands:
Best time: June to September.
Why: The beaches are warm, the seafood’s fresh, and the summer vibe is electric.
The Berkshires & Western Massachusetts:
Best time: Fall for foliage (late September to mid-October) and summer (July-August) for festivals and hiking.
Why: Leaf-peeping at its finest, plus Tanglewood concerts and farm-to-table dining.
By Air:
Boston Logan International Airport (BOS): The state’s major hub, with flights from all over the world. A quick hop on the T (Boston’s subway) or a rideshare takes you downtown.
Worcester Regional Airport (ORH): Small but mighty, great for central Massachusetts.
T.F. Green Airport (PVD): Located in Rhode Island, but often cheaper and just an hour’s drive to Boston or Cape Cod.
By Cruise Ship:
Many major cruise lines dock in Boston, making it a popular embarkation point for New England and Canadian itineraries. CruisePort Boston is centrally located in the Seaport District—just minutes from downtown hotels and attractions.
By Car:
I-90 (Mass Pike): Runs east-west from the Berkshires through Boston.
I-95: Loops around Greater Boston and continues south.
Route 6: The scenic way to Cape Cod.
By Train:
Amtrak’s Northeast Regional: Connects New York City, Washington D.C., and Boston.
MBTA Commuter Rail: Great for day trips to Salem, Lowell, Worcester, and more.
Required Documents:
f you’re a U.S. traveler, getting into Massachusetts is as easy as showing up—no passport or visa required. Just pack your driver’s license or government-issued ID, and you’re good to go.
For international travelers, you’ll need:
A valid passport.
A visa or ESTA (Electronic System for Travel Authorization) if you’re from a Visa Waiver Program country.
Always check the latest U.S. Customs and Border Protection regulations before you travel.
Massachusetts Itineraries
Top Things to do in Massachusetts
Road Trips
Massachusetts North Shore Coastal Drive — cruise from Boston to Rockport, stopping at Salem and Gloucester for history and beaches.
Mohawk Trail — a scenic byway through the Berkshires with stops for hiking, waterfalls, and charming small towns.
Cape Cod Route 6A — wind your way through historic towns, cranberry bogs, and ocean views all the way to Provincetown.
Route 2 to Mount Greylock — a foliage lover’s dream in autumn, ending with a hike up the state’s highest peak.
Pioneer Valley Loop — explore Northampton, Amherst, and the Connecticut River Valley’s farms, breweries, and colleges.
Music & Festivals & Fairs
Tanglewood (Lenox) — the Boston Symphony Orchestra’s summer home in the Berkshires.
Boston Calling (Boston) — a massive three-day music festival featuring top artists.
Green River Festival (Greenfield) — folk, roots, and indie tunes plus hot air balloons.
The Big E (West Springfield) — New England’s biggest fair with everything from giant cream puffs to concerts.
Lowell Folk Festival (Lowell) — one of the largest free folk festivals in the U.S.
State Parks Galore
Cape Cod National Seashore — dunes, beaches, and lighthouses galore.
Minute Man National Historical Park — walk the battlefields of the American Revolution.
Mount Greylock State Reservation — summit views, hiking trails, and Bascom Lodge.
Boston Harbor Islands National & State Park — a quick ferry ride from downtown Boston with hiking and picnic spots.
Walden Pond State Reservation — literary history and swimming in the footsteps of Thoreau.
Outdoor Escapes
Zipline through Zoar Outdoor (Charlemont) — high-flying fun in the Berkshires.
Biking the Cape Cod Rail Trail — 25 miles of scenic pedaling.
Kayaking on the Charles River (Boston & Cambridge) — city skyline meets calm waters.
Hiking the Blue Hills Reservation (Milton) — close to Boston, but feels like wilderness.
Skiing at Wachusett Mountain (Princeton) — winter fun just an hour from Boston.
City Adventures
Walk the Freedom Trail in Boston — 2.5 miles of Revolutionary history.
Catch a game at Fenway Park — even if you’re not a Sox fan, it’s a vibe.
Explore Salem — witches, maritime history, and modern fun.
Shop & dine in Newburyport — a charming coastal town with boutiques and seafood.
Art & culture in Worcester — the Worcester Art Museum, Mechanics Hall concerts, and Canal District restaurants.
Explore Cambridge — home to Harvard, MIT, indie bookstores, and killer coffee shops.
Springfield’s Basketball Hall of Fame — a slam dunk for sports fans.
New Bedford’s Whaling Museum & waterfront — dive into maritime heritage.
Plymouth — walk in the Pilgrims’ footsteps at Plymouth Rock and Plimoth Patuxet Museums.
Lowell’s mill history & canals — the birthplace of the Industrial Revolution with live music and festivals.
Where to Stay
Luxury
Boston Harbor Hotel (Boston): Five-star waterfront elegance with sweeping views.
Wheatleigh (Lenox, Berkshires): Gilded Age mansion turned luxury hotel with Michelin-level dining.
Chatham Bars Inn (Cape Cod): Beachside luxury and spa vibes.
Mid-Range
The Verb Hotel (Boston): Retro rock-n-roll meets modern comfort.
Hotel on North (Pittsfield, Berkshires): Boutique charm with easy access to local arts.
SeaCoast Inn (Hyannis, Cape Cod): Friendly, clean, and walkable to beaches.
Where to Eat
Classic Dishes
Clam chowder (creamy, not Manhattan!)
Lobster rolls (hot buttered or cold with mayo—your call)
Boston cream pie (it’s a cake, but hey, Boston invented it)
Oysters from Duxbury Bay or Wellfleet.
Must Try Restaurants
O Ya (Boston): A sushi experience that’s borderline life-changing.
Menton (Boston): French-Italian fine dining by celebrity chef Barbara Lynch.
The Port Hunter (Edgartown, Martha’s Vineyard): Locally sourced seafood and creative cocktails.
Woods Hill Table (Concord): Farm-to-table meets gourmet excellence.