Best Places to Visit in Massachusetts
Massachusetts is a state where American history meets New England charm, where rugged coastlines contrast with leafy mountains, and where quaint villages sit side by side with vibrant cities. Each season paints the landscape differently, but no matter when you visit, Massachusetts offers something that stays with you long after you’ve left. From my own journeys across the Bay State and for living there as a local while visiting family, here are some places I found exceptional, and I think you will too.
1. The Berkshires
First settled in the 1700s, this cultural and natural haven in western Massachusetts took my breath away with rolling green hills, tranquil lakes, charming villages, and a world-class arts scene made it feel like New England’s ultimate escape!
A 2.5-hour drive west from Boston (or 3 hours north from New York City) brought me to the Berkshires, where I spent four rejuvenating days — hiking along the Appalachian Trail, kayaking on Onota Lake, wandering through the inspiring collections at the Clark Art Institute.
I was mesmerized by live music under the stars at Tanglewood, exploring the thought-provoking MASS MoCA, visited Norman Rockwell Museum, and indulging in heavenly pastries and fresh coffee at Haven Café & Bakery in Lenox. Staying at the elegant, historic Red Lion Inn in Stockbridge was a highlight.
The Berkshires At a Glance
- Drive Time from Boston: ~2.5 hours west
- Best Time to Visit: Summer for music festivals, fall for foliage
2. Cape Cod
My in-laws had a house in the area so I got to visit Cape Cod often. I love the beaches there, the excitement of summer and the calm of fall and spring. The dunes and sailboat provide a romantic backdrop.
First explored by Europeans in 1602, this crescent-shaped peninsula on Massachusetts’ southeastern coast is the ultimate seaside escape — with windswept dunes, quaint fishing villages, endless beaches, and some of the best seafood I’ve ever tasted, it felt like summer distilled into one perfect destination.
Some great activities here are catamaran sails with Bay Spirit Tours, taking your dog to Pilgrim Bark Park in Provincetown, Cape Cod Rail Trail, spotting humpback whales, watching the sunsets, and of course all the beaches!
A 1.5-hour drive southeast from Boston, Cape Cod is a great day trip from the city but I've also enjoyed staying at Isaiah Hall Bed & Breakfast.
Cape Cod At a Glance
- Drive Time from Boston: ~1.5–2.5 hours southeast (depending on location)
- Best Time to Visit: Late spring through early
3. Martha’s Vineyard
First settled by Europeans in 1642, this idyllic island off the coast of Massachusetts stole my heart with its windswept beaches, iconic lighthouses, gingerbread cottages, and a relaxed seaside vibe that feels both luxurious and laid-back.
A short 45-minute ferry ride from Woods Hole brought me to the Vineyard, where I spent three dreamy days at Faraway Martha's Vineyard, biking along quiet country roads past stone walls and sheep pastures, admiring the whimsical gingerbread cottages in Oak Bluffs, browsing boutiques and art galleries in Edgartown, savoring fresh lobster rolls and oysters at a harbor-side shack, kayaking along the serene lagoons near Vineyard Haven, and watching the pastel skies melt into the horizon at Aquinnah Cliffs.
A food highlight was Larsen’s Fish Market in Menemsha. I ordered the clam chowder and a lobster taco and ate right on the dock, seagulls swirling nearby, the harbor slowly shifting into golden hour. It was messy, salty, and perfect.
Martha’s Vineyard At a Glance
- Ferry Time from Woods Hole: ~45 minutes
- Best Time to Visit: Summer for full seasonal activity; early fall for fewer crowds
4. Provincetown
I was a big fan of Provincetown, perched at the very tip of Cape Cod. I thought it was a rare gem — a colorful seaside town with charming clapboard cottages, lively art galleries, and sweeping Atlantic views. I loved its eclectic mix of history, creativity, and free-spirited energy — a place where you feel both the salt air of the ocean and the heartbeat of a tight-knit community. It’s a perfect blend of small-town intimacy and cultural vibrancy.
Driving the scenic stretch along Cape Cod, I made Pilgrim House Provincetown my base for a long weekend. I strolled along Commercial Street with its quirky shops and street performers, browsed local art in the Provincetown Art Association and Museum, took a whale-watching tour off the coast, hiked the windswept dunes of the Cape Cod National Seashore, and climbed the Pilgrim Monument for panoramic views over the town and harbor.
After exploring Commercial Street’s shops and galleries, I had dinner at The Mews Restaurant & Café. I ordered the pan-seared scallops with lemon beurre blanc and local vegetables. The view over the harbor, framed by soft lighting and laughter, made it feel like more than a meal, it felt like a celebration of place.
Provincetown At a Glance
- Drive Time from Boston: ~2.5–3 hours (or 90-minute ferry)
- Best Time to Visit: Summer for vibrant energy; fall for a quieter, golden-light version
5. Worcester, Massachusetts
Worcester, Massachusetts’ second-largest city was far more vibrant than I expected. Rolling New England hills frame its skyline, and historic red-brick mills blend with leafy parks, Gothic churches, and a growing collection of street art. The city’s energy feels like a mix of industrial grit, college-town creativity, and a revived foodie culture.
After arriving at Worcester Regional Airport (tiny but convenient) and staying for three days at AC Hotel by Marriott Worcester, I explored downtown’s restored Mechanics Hall, wandered Elm Park — one of the oldest public parks in the U.S. — and browsed galleries at the Worcester Art Museum, home to pieces that rival Boston’s collections. Murals and public art brighten streets around the Canal District, while Polar Park brings baseball and lively crowds to the city’s heart.
As a history buff, I checked out Salisbury Mansion, the only historic house museum in Worcester, and climbed Bancroft Tower for sweeping city views. I grabbed a famous “Worcester-style” hot dog at Coney Island Lunch — the neon sign outside is a landmark in itself.
6. Salem
I stumbled across Salem’s historic waterfront and felt like I’d stepped into another world — cobblestone streets lined with centuries-old houses, tall-masted ships moored at the wharf, and the salty tang of the Atlantic carried in on the breeze. The mix of maritime history and a vibrant modern vibe made it feel like a living time capsule with a touch of magic.
After a scenic forty-minute drive north from Boston along the rocky New England coast, I reached Salem, spent an unhurried day exploring, and stayed nearby at The Merchant, a boutique inn set in a restored 18th-century building just a short stroll from the harbor.
I wandered through the Salem Maritime National Historic Site, toured the tall ship Friendship of Salem, and ducked into the House of the Seven Gables for a literary-meets-historical journey. Later, I sipped coffee at a harbor-view café and lingered by the water as the fishing boats came and went — the rhythm of daily life blending with deep history.
Salem At a Glance
- Drive Time from Boston: ~40 minutes north
- Best Time to Visit: October for spooky season energy, spring/fall for calmer visits
7. Nantucket
I completely fell for Nantucket’s windswept charm — an island of shingled cottages, wide sandy beaches, and endless Atlantic horizons, its muted grays and weathered whites glowing softly under New England light. The whole place felt like a perfectly preserved seaside painting, with cobblestone streets and salty air lending it a timeless, almost dreamlike quality.
After a breezy two-hour ferry ride from Hyannis across Nantucket Sound, I arrived at the island, spent a sun-soaked weekend exploring, and stayed at the historic Jared Coffin House, right in the heart of town just steps from boutiques and cafés.
I cycled along quiet paths lined with wild roses, stretched out on the golden expanse of Surfside Beach, and wandered Siasconset’s bluff walk, where roses spilled over white picket fences and cottages seemed to tumble toward the sea. In the evening, I joined locals at the wharf to watch sailboats drift back under a pink-and-gold sky — the kind of simple, perfect moment that lingers.
My favorite lunxh was at Something Natural, tucked just beyond downtown. I ordered the turkey, cranberry, and stuffing sandwich on house-baked Portuguese bread, and took it to the beach. Eating barefoot in the sand with gulls circling above and the ocean gently curling at my feet, it was the kind of moment you don’t try to capture. You just live it.
Nantucket At a Glance
- Ferry Time from Hyannis: ~1 hour (fast ferry)
- Best Time to Visit: Summer for full island life, early fall for peaceful charm
8. New Bedford, Massachusetts
New Bedford’s a working harbor where scallop boats bob beside whaling-era warehouses, cobblestone streets wind past brick mills, and the scent of salt and diesel lingers in the air. The city felt like both a living seaport and a museum — layered with history yet undeniably alive.
After driving south from Boston for an hour through cranberry bog country, I arrived in New Bedford, spent a full day exploring, and stayed at The New Bedford Harbor Hotel, a boutique spot just a short walk from the waterfront.
I toured the New Bedford Whaling Museum, stood before towering scrimshaw and panoramic murals that told the story of America’s whaling past, and ducked into the Seamen’s Bethel, where Herman Melville once drew inspiration for Moby-Dick. Later, I wandered the working piers, watching crews unload scallops, then grabbed fish and chips at a dockside shack as gulls circled overhead. The city’s mix of industry and artistry gave it a raw, authentic beauty.
9. Lowell, Massachusetts
Lowell felt like walking through a living story of America’s Industrial Revolution, yet it had a creative, modern energy threaded through its galleries, cafés, and festivals.
After a quick forty-five–minute drive northwest from Boston, I reached Lowell, spent the day exploring, and stayed overnight at the UMass Lowell Inn & Conference Center, right along the Merrimack River and steps from downtown.
I toured the Lowell National Historical Park, wandered through restored textile mills filled with exhibits on mill girls and immigrant stories, and took a canal boat ride to see how water once powered the factories. Later, I explored the Brush Art Gallery, grabbed a plate of Cambodian noodles in the Acre neighborhood, and lingered in the evening light by the riverwalk as the Merrimack flowed steadily by — a reminder of both past and present strength.
Plan your visit:
- Where: Northern Massachusetts, Merrimack Valley
- Drive Time from Boston: ~45 minutes northwest
- Best Time: Fall for foliage and walking tours; spring for art festivals
Conclusion
Each of these places left me with a distinct sense of discovery — from the hidden beauty of natural springs and windswept islands to the grit and heritage of historic ports and mill towns. What ties them together is the way past and present intermingle: centuries-old stories still alive in the streets, landscapes that feel timeless yet welcoming, and communities that give each destination its own rhythm. Traveling through them, I felt both grounded in history and refreshed by the simple pleasures of place — moments that linger long after the journey ends.
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Booking Checklist
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4. Book your tours on Viator or Get Your Guide.
