Massachusetts Day Trips
Ready to unplug from the daily routine and take a day trip from the city? Well, you are in the right place! Massachusetts day trips offer a little bit of everything, including history, beauty, and small towns. I've always found it easy to plan memorable getaways without going far.
Whether you’re looking for family-friendly adventures, romantic outings, or solo explorations, Massachusetts is full of day trip destinations that are both accessible and rewarding as I found our on my recent four week road trip in December. Here are the ones I recommend, and I think you’ll enjoy them too.
Coastal MA Day Trips
Massachusetts has many incredible coastal and island destinations to visit on a day trip that easily extend into a relaxing weekend. Here are my favorites.
1. Martha’s Vineyard
Martha’s Vineyard is a perfect day trip but an even better weekend getaway! It's one of those dream destinations in Massachusetts that always feels magical every time we visit family here. Just a 45-minute ferry ride from Cape Cod, this island is incredibly beautiful and unique. If you visit in early December like we did, you will find empty beaches and affordable places to stay.
We started in Oak Bluffs (where you get off the ferry), which instantly won me over with its colorful gingerbread cottages. Walking past those homes felt like stepping into a dream, and the atmosphere was so unique and unforgettable.
From there, we drove to Edgartown, which had a more elegant and romantic feel. The historic captain’s houses, boutique shops, and waterfront restaurants gave the whole area such an exceptional energy, though hours were limited in the off season! Sitting by the harbor with a fresh muffin from Espresso Love was one of my favorite moments of the trip. Staying at 5-star Harbor View Hotel in Edgartown for two nights is just perfect for a romantic weekend.
Another highlight for me was exploring the Aquinnah Cliffs. The views of the colorful clay cliffs against the blue ocean were spectacular and felt like something out of a painting. It’s one of those underrated natural wonders that absolutely blew me away.
- Location: Map & Directions
We also spent time in Chilmark and Menemsha, where life slowed down and the sunsets over the harbor were simply the best I’ve ever seen.
One of my favorite highlights was visiting the Chilmark General Store. Sitting on the porch with a slice of pizza, surrounded by locals and travelers, gave me a real sense of community.
2. Provincetown, Massachusetts
Provincetown, Massachusetts is one of the best day trips from Boston. Why? Perched right at the tip of Cape Cod, it’s this hidden gem where ocean views, culture, and creativity all come together, somehow in a different way for everyone.
We began along Commercial Street, which I think is one of the coolest stretches in New England. There are the shops, art galleries and a diverse food scene.
One of my favorite discoveries was Pilgrim Bark Park, a playful spot that makes Provincetown extra special for dog lovers.
The beaches, of course, are unbeatable. Race Point and Herring Cove are both spectacular. I thought the sand dunes and waves made for the most romantic and peaceful walks.
- Location: Map & Directions
Climbing the Pilgrim Monument was another highlight because the views of Cape Cod Bay and the entire town were absolutely amazing. For me, Provincetown is the best mix of history, art, nature, and quirky charm, making it one of my favorite underrated Massachusetts getaways.
3. Wellfleet, Massachusetts
Wellfleet, Massachusetts, has to be one of the most amazing hidden gems on Cape Cod. I love planning a day trip here. Why? Nestled between the Atlantic Ocean and Cape Cod Bay, this underrated spot is the best mix of coastal charm, natural beauty, and cool local culture.
We started the day at Wellfleet Harbor, where colorful boats bobbed on the water and the lively energy of the small town instantly pulled me in. I loved wandering through the little shops and galleries, each one filled with unique and interesting finds that made me want to take a piece of Wellfleet home with me.
Of course, I couldn’t skip the beaches. Cahoon Hollow Beach is my favorite, with its dramatic cliffs and spectacular views that made me feel both small and inspired. Walking the shoreline was such a joyful experience, and the Beachcomber—a cool, casual spot right on the dunes—was the perfect place to grab lunch with an ocean breeze.
Wellfleet is also famous for its oysters, and tasting them fresh at a local restaurant like The Wicked Oyster and Pearl Restaurant & Bar honestly one of the coolest foodie experiences I’ve ever had. It felt affordable yet exceptional, like enjoying the absolute best of Cape Cod’s flavors in the most authentic way possible.
- Location: Map & Directions
- Check prices and availability at 2-star Wellfleet Motel.
We wrapped up the day exploring the Wellfleet Bay Wildlife Sanctuary, where the trails through salt marshes and woods offered quiet, romantic views of the bay. For me, Wellfleet is the ultimate Cape Cod getaway—vibrant, exciting, and absolutely one of my favorite places to spend a weekend by the sea.
4. Good Harbor Beach
Good Harbor Beach in Gloucester is one of my absolute favorite seaside day trips in Massachusetts. Just about an hour north of Boston, this hidden gem on Cape Ann is so peaceful (even when it's busy in August!)
The first thing that struck me was the soft white sand...it’s so inviting and makes for the coolest barefoot walks along the shoreline. At low tide, I loved being able to stroll right out to Salt Island, which felt like such an unusual and exciting adventure. It’s one of those little details that makes Good Harbor stand out as one of the best beaches in New England.
We spent hours swimming in the refreshing Atlantic waves and lounging under the sun. The views of the dunes and water created such a dreamy backdrop that I wished the day would never end. It honestly felt like a brilliant idea for a summer day trip with my husband and son.
What I also loved was how family-friendly and affordable the whole experience was. Kids were building sandcastles (my son made a new friend that way!), couples were taking romantic walks, and surfers were catching waves. It had this amazing energy that made everyone feel welcome. Parking can fill up fast, but arriving early turned out to be the smartest move we made.
- Location: Map & Directions
By sunset, the sky lit up in spectacular colors, and I thought it was one of the most magical moments I’ve ever experienced on the Massachusetts coast. Good Harbor Beach’s truly unforgettable as a day trip!
5. Ipswich - 30 miles north of Boston
Ipswich, Massachusetts, has to be one of the most spectacular hidden gems on the North Shore. Just about 30 miles north of Boston, it’s the absolute best mix of small-town charm, coastal beauty, and amazing history, making it perfect for a quick day trip, even if you just have 3 or 4 hours to get away from the city.
We started in the town center, where historic homes, cozy cafés, and little shops gave Ipswich such a vibrant and welcoming vibe. I loved wandering the streets and taking in the colonial architecture...it felt both unique and underrated compared to bigger New England towns.
Of course, Crane Beach was the highlight for me. With its miles of soft sand and rolling dunes, it’s one of the coolest and most beautiful beaches in Massachusetts. Walking along the shoreline as the waves crashed felt like pure magic, and it’s easy to see why people call it one of the best spots on the East Coast.
Another favorite experience was visiting Castle Hill on the Crane Estate. Strolling down the Grand Allée toward the ocean, with gardens and the stately Great House behind me, was unforgettable. It was an exceptional blend of history, elegance, and natural beauty that made the whole day feel dreamlike.
- Location: Map & Directions
And I can’t forget the food—Ipswich is famous for its clams, and tasting fresh fried clams at a local seafood at Luna Mare Cuisine was one of the most delicious parts of the trip. For me, Ipswich is an amazing and affordable New England getaway, packed with hidden treasures and coastal charm that make it one of my favorite towns to visit.
6. Marblehead
Marblehead enchanted me with its postcard-perfect harbor views, steeped-in-history streets, and timeless New England elegance. This coastal gem felt like a living painting — weathered captain’s homes trimmed in white, narrow lanes paved with centuries-old cobblestones, and sailboats bobbing in a sparkling harbor that once fueled America’s early maritime spirit. Everywhere I turned, the town seemed to whisper stories from its seafaring past.
A scenic 45-minute drive north from Boston brought me to Marblehead’s Old Town, where I spent the afternoon wandering through a maze of colonial-era streets lined with boutiques, galleries, and cozy cafés.
I loved stopping for creamy clam chowder and a lobster roll at The Landing, and catching golden-hour views of the harbor from Chandler Hovey Park by the lighthouse. I stayed two peaceful nights at the 3-star Harbor Light Inn, a charming 18th-century inn with fireplaces, canopy beds, and a courtyard pool, pure New England comfort. Prices here were what you’d expect from a boutique coastal town, but the experience felt utterly worth it.
- Location: Map & Directions
- Check prices and availability at The Hotel Marblehead
My personal highlight was watching the sun set behind the boats from Chandler Hovey Park.
Day Trips Around Boston
If you are looking for a lot to do in one day, head to Boston. You can visit museums, parks, go on scenic waterfront walks and dine at great restaurants... Here are my favorites.
7. Spectacle Island
Spectacle Island felt like a hidden retreat just beyond the city skyline, a place where Boston’s bustle melted into sea breezes, open skies, and panoramic harbor views.
Once a landfill turned lush green oasis, the island now feels serene, with rolling hills, sandy beaches, and trails lined with wildflowers that sway above the sparkling blue water.
A scenic 25-minute ferry ride from Long Wharf in downtown Boston brought me here. I spent the afternoon collecting bits of sea glass along the shore (a local pastime). Though there’s no overnight lodging on the island, it makes for one of the most restorative day trips.
8. Boston, Massachusetts
Boston captivated me with its seamless blend of history, sophistication, and coastal charm. Strolling through Beacon Hill felt like stepping into a period painting — gas-lit streets lined with Federal-style row houses, polished brass knockers gleaming on deep-red brick facades, and the faint scent of sea air drifting in from the harbor. The whole city seemed to glow in the evening light
A scenic 15-minute walk from the Common brought me to the North End, Boston’s beloved “Little Italy.” I spent the afternoon exploring cobblestone alleys, savoring espresso and cannoli at the famous Mike’s Pastry, and popping into independent boutiques along Hanover Street.
Later, we dined at the cozy Neptune Oyster (their lobster roll was nothing short of perfection) before watching the sunset from Fan Pier Park, where the skyline shimmered across the harbor. I stayed two nights at Omni Boston at the Seaport which won the prestigious AAA Four Diamond award so you can trust that it's quality place.
- Location: Map & Directions
My personal highlight was wandering through the historic gas-lit streets of Beacon Hill.
9. Cambridge
Our second day in Boston was spent getting to know Cambridge, and we needed a whole day ! Cambridge, Massachusetts, has to be one of the most unique and exciting day trips I’ve ever taken. Just across the Charles River from Boston, it’s so close yet feels like its own hidden gem with a vibrant personality that instantly won me over.
We started in Harvard Square, which might be the coolest hub of energy I’ve experienced. Street performers, bookshops, and historic buildings gave it an amazing mix of old and new.
Exploring Harvard Yard was unique. The history, the ivy-covered brick buildings, and the sheer buzz of student life made it feel like stepping into a world where knowledge and culture collide.
We also wandered over to Kendall Square, known as the “most innovative square mile on the planet,” and I found it so interesting to see the sleek modern architecture paired with cool public art and awesome food spots.
It’s the best place if you love discovering unusual but inspiring city vibes that completely won me over.
Cambridge, MA is a food lover’s dream. Try the risotto or short ribs at Oak Bistro or enjoy the garden courtyard at Harvest.
Later, walking along the Charles River Esplanade gave us such a romantic and peaceful end to the day.
- Location: Map & Directions
For me, Cambridge is a brilliant idea for a weekend getaway: it’s vibrant, intellectual, and absolutely one of my favorite places to explore in New England.
Inland MA Day Trips
Discover new places on a day trip inland in Massachusetts! Here are some unique choices.
10. Acushnet
Acushnet, Massachusetts, feels like one of those hidden gems you almost don’t want to share because it’s just that special. Nestled near New Bedford, this small town makes for one of the most underrated day trips on the South Coast, and I couldn’t believe how much I discovered in just one weekend.
We started our adventure with a walk through Acushnet’s charming town center, where the historic buildings and small shops created such a joyful and vibrant atmosphere. It’s not the kind of place you rush through—it’s the kind of place you savor, and for me that’s the best kind of day trip vibe.
One of my favorite stops was Acushnet Creamery, which might honestly be the absolute best spot for homemade ice cream. I couldn’t resist snapping photos of my cone...it was that picture-perfect and delicious. Moments like that are what make a getaway feel so sweet and memorable.
Another highlight for me was exploring the local farms and orchards. Acushnet is known for its apples, and spending the afternoon picking fruit in the crisp air felt like such an exciting and affordable way to enjoy the outdoors. It’s one of those unusual but awesome experiences you don’t always find so close to the coast.
- Location: Map & Directions
We also found ourselves stopping by the peaceful parks and trails, where I loved soaking in the natural beauty. The magic here is that it’s both relaxing and adventurous—a cool mix of quiet New England charm and lively seasonal events. For anyone looking for a unique, underrated, and spectacular Massachusetts getaway, Acushnet is a dream of a day trip.
11. Lake Chaubunagungamaug
Massachusetts’ Webster Lake is the colloquial name for what’s officially called Lake Chargoggagoggmanchauggagoggchaubunagungamaugg.
The lake, with the longest name in the United States and the third longest in the world, was named after English colonialists first arrived in the area, and is a Nipmuk Indian name roughly meaning, “neutral fishing and meeting place for white men and Native Americans.”
Locals balked at a suggested name change to Lake Chaubunagungamaug in the 1950’s, and the name remains a source of pride for those who can pronounce it.
- Location: Map & Directions
Webster Lake is popular for swimming, fishing and boating. During the winter months, it’s used for ice fishing and snowmobiling.
12. Springfield, Massachusetts
Springfield, Massachusetts, surprised me in the best way—it’s one of those underrated cities that makes for such a cool and affordable day trip in Western Mass. Just knowing it’s near the Connecticut River gave our adventure a vibrant setting right from the start.
We kicked things off at the amazing Springfield Museums, which are all clustered around the Quadrangle. I loved that you could hop from an art museum to a science museum to a history museum all in one spot—it felt like the absolute best deal for a curious traveler like me. My favorite was the Dr. Seuss National Memorial Sculpture Garden, which was joyful, colorful, and so unique to Springfield (since it’s his hometown!).
Another highlight for me was the Naismith Basketball Hall of Fame. Even if you’re not a huge sports fan, it’s one of the most exciting attractions in the city. I found it interesting to see the history, interactive exhibits, and the way it celebrated the magic of the game. It’s definitely one of the coolest things to do with family or friends.
We also explored Forest Park, which is spectacular in any season. I loved strolling along the trails and finding quiet, romantic spots near the ponds and gardens. In the winter, the Bright Nights holiday lights transform it into something truly magical, making Springfield a dream getaway for the holidays.
- Location: Map & Directions
By the end of the day, I felt like Springfield was an exceptional hidden gem in Massachusetts. Between the history, culture, and fun, it’s one of my favorite cities for a weekend adventure that’s exciting, unusual, and unforgettable.
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.
