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.
Best Places to Visit in Western / Central Massachusetts
I head here when I'm in the mood for outdoor adventure, history, and local culture.
1. The Berkshires
This area in western Massachusetts near the New York border is my absolute best hidden gem getaway when I lived nearby in New York for 10 years, just across the border.
First we enjoyed driving through rolling hills and tiny towns, and that road trip alone was an amazing experience that felt peaceful, scenic, and kind of magical in a quiet way.
Chris and I checked into The Cornell Inn, Lenox & The Berkshires (from $175/night) for two days, close to Tanglewood, and it instantly felt like a romantic and family-friendly dream with charming rooms and that classic Berkshire vibe.
After settling in, we wandered through downtown Lenox which was vibrant, cool, and full of unique shops, making it one of my favorite small town experiences in Massachusetts. We had heavenly pastries and fresh coffee at Haven Café & Bakery in Lenox.
The next morning we headed to Tanglewood, and honestly this was the absolute best part, an exciting and joyful music-filled experience surrounded by nature.
Later we explored Stockbridge itself, which felt like an unusual mix of history and art, especially visiting the Norman Rockwell Museum which is a true cultural gem.
We grabbed lunch at a local café and it was affordable, cozy, and just the best kind of small-town food moment.
In the afternoon we drove to Mount Greylock, near North Adams, and hiking there was a spectacular experience with views that were jaw-dropping and totally worth it.
North Adams surprised us with MASS MoCA, which was one of the coolest and most interesting art spaces I’ve ever seen, truly a brilliant idea in an old factory.
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.
I was absolutely mesmerized by live music under the stars at Tanglewood, my favorite highlight.
2. Worcester
Massachusetts’ second-largest city (less than an hour from Boston!) was far more vibrant than I expected, and I think it's one of the best places for a quick weekend escape.
We started the day driving in, watching the landscape soften into open fields, old barns, and tree-lined roads that immediately set a peaceful, unhurried mood.
My favorite part was just walking together along the quiet roads, the air crisp and clean, with the kind of stillness that makes conversation feel easier and more meaningful.
As a history buff, I first checked out Salisbury Mansion, the only historic house museum in Worcester, and tgeb 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.
I loved browsing through local shops filled with vintage finds, handmade goods, and bits of Pacific Northwest character that felt personal rather than polished.
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.
A hidden highlight was pulling off the road to take in the scenery—wide skies, distant evergreens, and that soft Washington light that makes everything feel calm and grounded. We spent a relaxing night at AC Hotel by Marriott Worcester.
Learning a bit about the area’s farming roots and rural history gave the day a deeper sense of place, reminding me how connected this region still feels to the land.
Next day, we strolled through Elm Park (one of the oldest public parks in the U.S.) and browsed galleries at the Worcester Art Museum.
What I loved best:
Murals and public art brighten streets around the Canal District, my favorite highlight.
Best Islands in Massachusetts
The islands offer a classic New England escape, known for their stunning beaches and historic lighthouses.
3. Martha’s Vineyard
On my first visit decades ago, 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 visiting my husband's family.
The boat ride itself was an amazing experience, salty air, happy vibes, and views that felt like a dream.
Once we arrived, the island instantly felt like a hidden gem, relaxed, vibrant, and totally different from the mainland.
First thing we did was rent bikes, which I think is the best and most joyful way to explore. After biking, we stopped in Edgartown, one of the most beautiful and interesting places on the island.
I loved walking past the historic homes and harbor, it felt classic, cool, and kind of timeless. Later we grabbed seafood at Quarterdeck Restaurant right by the water, and honestly it was some of the best food ever.
The afternoon was spent at South Beach, which was an awesome and spectacular experience. We swam, relaxed, and watched the waves, and it felt affordable and peaceful for such a popular spot.
In the evening we headed to Oak Bluffs, which is vibrant and full of unique energy.
We stayed out late, exploring, and enjoying the magic that filled the streets.
The next morning was slower, coffee first, then a drive to Aquinnah Cliffs. Seeing the cliffs in person was unbelievable and honestly underrated for how stunning they are.
We stood there quietly, soaking it in, and it became one of my most memorable experiences.
Before leaving, we shopped locally, finding unusual gifts and cool art.
What I loved Best
My 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. Nantucket
Ready for a coastal escape full of history and understated luxury? Nantucket completely won us over. This small island felt timeless and romantic, making it one of our favorite seaside getaways.
We started by wandering the historic downtown, where cobblestone streets, gray-shingled buildings, and flower-filled window boxes created a storybook setting at every turn.
My favorite stop was the Whaling Museum, where we learned about Nantucket’s maritime past and climbed to the rooftop deck for sweeping views over the harbor—an unforgettable perspective on the island’s history.
Downtown, we discovered charming boutiques, bookstores, and cafés that encouraged us to slow down, browse, and savor the island’s relaxed rhythm. Next, a walk along the harbor led us past sailboats bobbing in the water, with salty air and sunlight sparkling off the waves—it felt effortlessly romantic.
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
Later, we ventured beyond town to explore quiet beaches and scenic roads, where dunes, hydrangeas, and open ocean views made every drive feel cinematic. As evening arrived, we returned downtown, where soft lantern light, lively restaurants, and the hum of conversation gave the island a warm, inviting energy well into the night.
Best Places to Visit in Massachusetts - South Coast & Cape
This region is at its most maritime, where historic seaports, sandy beaches, and coastal towns define the landscape.
5. Provincetown
For me, this is one of the coolest East Coast beach towns I’ve ever explored. In addition, Provincetown offers miles of shoreline, dunes, and a thriving creative community.
After driving along the scenic stretch along Cape Cod, I made 3-star Pilgrim House Provincetown (from $77/night) my base for a relaxing long three day weekend.
First, we strolled along Commercial Street with its quirky shops and street performers, then browsed local art in the Provincetown Art Association and Museum. After lunch, we took a catamaran sail with Bay Spirit Tours (whale-watching tour are also an option in season from mid-April to October).
I thought it was amazing that you can take your dog to Pilgrim Bark Park in Provincetown! After, we enjoyed a beautiful sunset, followed by dinner at the hotel.
Next day, we hiked the windswept dunes of the Cape Cod National Seashore, and climbed the Pilgrim Monument for panoramic views over the town and harbor. The dunes and sailboat provide a romantic backdrop for an easy weekend getaway from Boston.
A short walk brought us to the dunes and nearby beaches, where winding paths through tall grass opened up to sweeping ocean views, giving us a peaceful chance to explore side by side in the salty air.
What I loved best:
After exploring Commercial Street’s shops and galleries, we had a delicious 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. 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.
We stayed at The New Bedford Harbor Hotel for two days, a boutique spot just a short walk from the waterfront.
New Bedford is known as the Whaling City and it’s near the ocean which makes everything feel vibrant, salty, and strangely romantic.
We spent hours at the New Bedford Whaling Museum and it was honestly my favorite, such an interesting and unusual deep dive into maritime life.
The waterfront area near the harbor is awesome for strolling, seafood stops, and seeing colorful boats which you can see in my photos.
I thought the historic district was a hidden gem with cobblestone streets, old buildings, and an amazing underrated charm that felt authentic.
Food here surprised me the most, with fresh scallops, local bakeries, and some of the best Portuguese dishes we’ve ever tried.
Being near Providence and not far from Boston makes it a perfect family or romantic getaway without the big city chaos.
I found the art scene super cool and unique, with small galleries, murals, and creative spaces tucked into unexpected corners.
Sunset by the water was pure magic for us, the kind of experience that feels calm, exciting, and quietly unforgettable.
What I loved best:
The city’s mix of industry and artistry gave it a raw, authentic beauty and was a standout.
Best Day Trips in Eastern Massachusetts
This region offers a rich mix of history, culture, and modern attractions—all within easy reach of one another.
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.
I always say Salem is my favorite fall destination but honestly it’s an amazing underrated gem year round, not just spooky season.
Walking through the historic streets near the harbor feels like stepping into a dream, with old houses, cobblestones, and that cool ocean air.
The Salem Witch Museum and all the unusual historic sites are such a unique experience, and we learned so much while still having fun.
I loved how everything is so walkable, especially around downtown Salem near Essex Street which is packed with interesting shops and cafes.
There are so many hidden gems here, from small art galleries to cozy coffee spots that felt affordable and welcoming.
We spent hours just exploring, and soaking in the joyful energy that makes Salem feel exciting and alive.
One of the coolest parts for me was the waterfront near Salem Maritime National Historic Site, it’s peaceful but still spectacular.
Salem is also surprisingly romantic, making it a brilliant idea for couples or even a fun family trip with lots to do.
The food scene was another highlight, with awesome seafood and cozy restaurants that felt local and authentic.
I think what makes Salem so special is how it blends dark history with creative modern vibes, which is such a unique balance.
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. 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 for two days 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.
First thing, I loved walking around the city on foot and feeling how each area told a different story through its architecture, culture, or food.
Boston’s history as a major port and gateway for immigrants, particularly from Ireland, Italy, and Eastern Europe, shaped much of the city’s identity. What I found most interesting from talking to locals is how strongly people identify with their neighborhoods rather than just the city itself. Areas like Beacon Hill, the North End, and Back Bay all feel distinct, each with their own character and traditions.
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.
We ended our fist day with an amazing romantic dinner at Atlantic Fish from freshly caught fish from local waters.
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.
Local tips:
Getting to Boston and around the city is very easy. If you’re arriving from the airport, you can take a taxi or rideshare for around $25–$40 USD, depending on traffic. The subway system, known as the “T,” is also convenient and costs about $2.40 USD per ride. I highly recommend walking whenever possible, as many of Boston’s top attractions are close together.
If you want to truly experience Boston’s history and food scene, I highly recommend booking a guided tour. In our experience, a good guide brings the stories to life and helps you understand the city beyond what you’d get exploring on your own.
9. Lowell
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!
After a quick forty-five–minute drive northwest from Boston, we reached Lowell, and stayed at the UMass Lowell Inn & Conference Center for two days, right along the Merrimack River and steps from downtown.
First, 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).
Walking the historic canals felt like stepping into an unusual and interesting industrial dream.
We thought the Lowell National Historical Park was absolutely the best way to understand the city’s mills, stories, and hardworking spirit.
The red brick buildings mixed with modern art spaces gave me an amazing underrated vibe that felt cool and authentic.
I kept thinking how affordable and exciting this destination is compared to other Massachusetts cities near Boston and Cambridge.
Downtown Lowell surprised us with awesome coffee shops, local restaurants, and live music that felt joyful and full of life.
One of my favorite moments was strolling near Market Street at night, which felt vibrant, romantic, and a little magical.
We explored museums and galleries all weekend and i swear every corner felt unique and full of hidden stories.
The food scene was a brilliant idea for food lovers, from Cambodian flavors to classic American comfort, truly exceptional.
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.
