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
This area in western Massachusetts near the New York border is my absolute best hidden gem getaway. 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 lived nearby!
We drove about two hours from Boston and suddenly the hills felt magical, green, and totally underrated.
This region near Albany NY has the best mix of culture, nature, and affordable dreamy escapes.
One favorite experience was waking up to foggy mountains that felt like a quiet romantic dream.
Not every place feels this peaceful yet vibrant, and the Berkshires really surprised us.
You’ll find cool small towns like Lenox and Stockbridge tucked between rolling hills and forests.
My favorite part was how everything felt slow, joyful, and refreshingly unusual in the best way.
We spent a weekend exploring art museums, scenic drives, and cozy cafes that felt very local.
The hiking here is spectacular and near Mount Greylock, which is the highest point in Massachusetts.
Sometimes we just pulled over to take photos because the views were that amazing.
This area is perfect for a family trip without big crowds.
I loved how the Berkshires feel like a secret even though it’s close to major cities.
Food spots were interesting and creative, with farm fresh menus and friendly vibes everywhere.
Staying in a charming inn felt like a brilliant idea and honestly a cool experience.
The mix of music festivals, theaters, and nature makes it one of the most unique regions.
We never felt rushed, which made the whole experience more meaningful and relaxing.
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 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.
2. Cape Cod
Chris and I both absolutely love Cape Cod, and have been many times. This is one of my favorite places to visit on the coast of Massachusetts, plus, my in-laws have a house in the area so I get to visit often without spending a lot.
We love driving over the Sagamore Bridge and instantly feeling that magic beach energy kick in.
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.
A 1.5-hour drive southeast from Boston, Cape Cod is a great day trip from the city but we've also enjoyed staying at 3-star Isaiah Hall Bed & Breakfast for two days. 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 !
One of my favorite things is how each town feels unique and interesting, like little hidden worlds waiting to be explored.
Chatham has this romantic, postcard vibe that feels perfect for a weekend getaway, especially near the lighthouse.
Provincetown is vibrant and exciting, packed with art galleries, cool shops, and some of the most fun people watching ever.
We always say the seafood here is the best experience, and grabbing fresh lobster rolls feels almost mandatory.
There are so many underrated bike trails, especially along the Cape Cod Rail Trail, which is a brilliant idea for seeing more without driving.
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
For me, Martha’s Vineyard is one of the most magical coastal escapes in New England, a place where time slows down and every moment feels a little more intentional.
We arrived by ferry, the salty air and gentle rocking of the water instantly signaling that we had left everyday life behind.
Our days began with bike rides along quiet paths, passing hydrangea-lined roads, lighthouses, and stretches of coastline that felt impossibly serene.
Edgartown charmed us right away, with its white clapboard houses, striped awnings, and harbor views that invited us to wander hand in hand without any real plan.
We spent an afternoon in Oak Bluffs, where the colorful gingerbread cottages felt playful and romantic all at once, like stepping into a storybook.
One evening, we shared fresh seafood overlooking the water—simple, perfectly prepared, and made even better by the golden sunset stretching across the harbor.
I loved ducking into small local shops filled with nautical art, handmade jewelry, and thoughtful souvenirs that captured the island’s easy elegance.
A quiet beach walk became an unexpected highlight, with soft sand underfoot, waves humming in the background, and the feeling that the rest of the world had gently faded away.
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.
For me, I loved walking the city on foot and feeling how each area told a different story—whether 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.
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.
5. Provincetown
For me, 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.
After 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.
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, 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 industry, college-town creativity, and a revived foodie culture.
Located right in central Massachusetts near Boston and Providence, Worcester feels like an easy weekend getaway without the chaos or prices of bigger cities.
After arriving at Worcester Regional Airport (tiny but convenient) and checking into AC Hotel by Marriott Worcester for three days, 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.
What I loved best:
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.
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.
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. 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. 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.
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.
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.
10. Lowell, Massachusetts
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.
