Best Places to Visit in Massachusetts
Searching for the best places to visit in Massachusetts? Well, you are in the right place! 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, The Bay State offers something that stays with you long after you’ve left. From my own four week road trip across the Bay State, here are some places I found exceptional, and I hope you will too.
1. The Berkshires
First settled in the 1700s, this cultural and natural haven in western Massachusetts took my breath away and made it feel like New England’s ultimate escape when I moved here!
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 at the 3-star Courtyard by Marriott Lenox Berkshires (around $125/night) hiking along the Appalachian Trail, kayaking on Onota Lake, wandering through the inspiring collections at the Clark Art Institute.
- Location: Western Massachusetts, in the Appalachian Mountains near the New York border
- Drive Time from Boston: ~2.5 hours west
- Location: Map & Directions
- Best Time to Visit: Summer for music festivals, fall for foliage
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.
What I loved Best
When we went back in the spring, staying at the elegant, historic 4-star Red Lion Inn in Stockbridge was a highlight as well.
2. Cape Cod
This is one of my favorite places to visit on the coast of Massachusetts! My in-laws had a house in the area so I got to visit often. What I love most are the beaches there, the excitement of summer and the calm of fall and spring. The dunes and sailboat provide a romantic backdrop for an easy weekend getaway from Boston.
First explored by Europeans in 1602, this crescent-shaped peninsula on Massachusetts’ southeastern coast is the ultimate seaside escape — with dunes, endless beaches, and some of the best seafood I’ve ever tasted.
Some great activities here are catamaran sails with Bay Spirit Tours, taking your dog to Pilgrim Bark Park in Provincetown, and Cape Cod Rail Trail !
- Location: Southeastern Massachusetts, extending into the Atlantic Ocean as a curved peninsula south of Boston
- Drive Time from Boston: ~1.5–2.5 hours southeast (depending on location)
- Location: Map & Directions
- Best Time to Visit: Late spring through early
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 3-star Isaiah Hall Bed & Breakfast for two days.
What I loved Best
Spotting humpback whales, watching the sunsets, and (of course!) all the beaches were my personal highlight!
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, cottages, and a relaxed seaside atmosphere.
A short 45-minute ferry ride from Woods Hole brought me to the Vineyard, where I spent three dreamy days at 3-star 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 near Vineyard Haven, and watching the pastel skies melt into the horizon at Aquinnah Cliffs.
- Location: An island off the southern coast of Massachusetts, in the Atlantic Ocean south of Cape Cod
- Ferry Time from Woods Hole: ~45 minutes
- Location: Map & Directions
- Best Time to Visit: Summer for full seasonal activity; early fall for fewer crowds
What I loved Best
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.
4. Things to Do in Boston
This capital is one of my places to visit in "the Bay State" when I want a mix of culture, cafés, and lots of history. In fact, arriving in this city to me feels like stepping into a city where every brick has a story — from the cobbled lanes of the Freedom Trail to the sleek glass skyline along the harbor. My stay at The Langham, Boston was very comfortable and the hotel won both the AAA Four Diamond and the Forbes Four Star award so you can trust that it's a quality place.
We stopped at The Merchant Boston in Downtown Crossing for an outdoor lunch in June and I loved their Seafood Bolognese with amazing Pecorino Romano, pasta and warm focaccia.
By day, I wandered through Boston Common and along Beacon Hill’s gaslit streets, then detoured through the bustling waterfront to watch ferries cut across the harbor. Each neighborhood felt like a different layer of Beantown’s long history, stitched together with a distinctly modern energy.
We ended our fist day with an amazing romantic dinner at Atlantic Fish from freshly caught fish from local waters.
- Location: Eastern Massachusetts along the Atlantic coast, at the mouth of the Charles River
- Map & Directions
What I loved best:
One afternoon, craving something casual and lively, I ducked into El Pelón Taquería near Fenway. A plate of spicy carnitas tacos and fresh guacamole became the perfect fuel before weaving through the Red Sox crowds and soaking in the buzz of game day.
5. Provincetown
Perched at the very tip of Cape Cod, this is one of the coolest East Coast beach destinations towns I’ve ever explored. Provincetown offers miles of shoreline, dunes, and a thriving creative community.
Driving the scenic stretch along Cape Cod, I made 3-star Pilgrim House Provincetown my base for a long three day 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.
- Location: At the northern tip of Cape Cod in Massachusetts, along the Atlantic Ocean
- Drive Time from Boston: ~2.5–3 hours (or 90-minute ferry)
- Map & Directions
- Best Time to Visit: Summer for vibrant energy; fall for a quieter, golden-light version
What I loved best:
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 enjoyed with the view over the harbor on a romantic evening out with Chris, my personal highlight.
6. Worcester, Massachusetts
Massachusetts’ second-largest city was far more vibrant than I expected, and I think it's one of the best places for a quick weekend escape. For me, 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.
We love Livia’s Dish, family-owned and operated breakfast & lunch spot that serves amazing crepes, stuffed pancakes, omelets, paninis, prepared fresh and with quality ingredients.
- Location: Central Massachusetts in the heart of New England, west of Boston
What I loved best:
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 and my a standout.
7. Salem
This is one of my favorite coastal towns to visit because of its wonderfully walkable downtown filled with character. I find it’s easy to get to from Boston, and in early fall I can enjoy crisp autumn air while still having warm-enough afternoons to stroll along the waterfront and visit the museums.
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 for four unhurried days, 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.
- Location: Northeastern Massachusetts on the North Shore, along the coast north of Boston
- Drive Time from Boston: ~40 minutes north
- Location: Map & Directions
- Best Time to Visit: October for spooky season energy, spring/fall for calmer visits
What I loved best:
Later, I sipped coffee at Jaho Coffee Roaster & Wine Bar and lingered by the water as the fishing boats came and went, my personal highlight.
8. Nantucket
Ready for a history-rich, picture-perfect coastal town? I completely fell for the island’s windswept charm — an island of cottages, wide sandy beaches, and endless Atlantic horizons.
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.
- Location: An island off the southern coast of Massachusetts, in the Atlantic Ocean southeast of Cape Cod
- Ferry Time from Hyannis: ~1 hour (fast ferry)
- Map & Directions
- Best Time to Visit: Summer for full island life, early fall for peaceful charm
What I loved best:
My favorite lunch 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 was my personal highlight
9. New Bedford, Massachusetts
There’s something about New Bedford that instantly made me feel like I’d discovered a coastal treasure with deep roots and it instantly became one of my favorite weekend getaways when we moved to the East Coast.
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 for two days, 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 checked out the working piers, watching crews unload scallops, then grabbed fish and chips at a dockside shack as gulls circled overhead.
- Location: Southeastern Massachusetts on the Acushnet River, along Buzzards Bay on the Atlantic coast
- Map & Directions
What I loved best:
The city’s mix of industry and artistry gave it a raw, authentic beauty and was a standout.
10. Lowell, Massachusetts
Set along the Merrimack River like a proud industrial landmark reborn, this is one of the most fascinating small cities I’ve explored in Massachusetts, and I think it's one of the absolute best places to experience New England history in a modern setting!
After a quick forty-five–minute drive northwest from Boston, we reached Lowell, spent the day exploring, and stayed at the UMass Lowell Inn & Conference Center for two days, right along the Merrimack River and steps from downtown.
The Whistler House Museum of Art is a must see attraction, the birthplace of the renowned artist James McNeill Whistler (born in 1834), dedicated to art (especially 19th- & 20th-century American art).
My husband, so and 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, and grabbed a plate of Cambodian noodles in the Acre neighborhood
- Location: Northeastern Massachusetts in the Merrimack Valley, northwest of Boston
- Drive Time from Boston: ~45 minutes northwest
- Map & Directions
- Best Time: Fall for foliage and walking tours; spring for art festivals
What I loved best:
For me, Lowell is one of the best places to visit in Massachusetts because it's historic, affordable, and hope you will love it too!
Lingering in the evening light by the riverwalk as the Merrimack flowed steadily by — a reminder of both past and present strength was my personal highlight.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
5. If you are planning to visit more than three national parks in the next 12 months, buy the America the Beautiful Pass.
