17 AMAZING Boston Day Trips in 2025 (By a Local)
Boston is one of those cities that has it all — history, charm, and lobster rolls on every corner — but what really makes it shine is how easy it is to escape. Within just a few hours, you can stroll through cobblestone villages, hike mountains, chill on beaches, or even sail to an island that feels like another world.
As a local who’s explored every corner of New England, I’ve rounded up my 17 favorite Boston day trips for 2025 — all doable by car, train, or ferry. Whether you’re craving nature, small-town charm, or a dose of American history, these getaways will make you fall in love with the region all over again.
1. Salem, Massachusetts – Witchy Vibes and Waterfront Charm (35 minutes)
You can’t talk Boston day trips without mentioning Salem. Famous for its 1692 witch trials, this coastal town has embraced its spooky past with quirky museums, ghost tours, and an irresistible Halloween atmosphere.
Even outside October, Salem is worth the trip — check out the Peabody Essex Museum, explore the harbor, and grab a lobster roll by the waterfront. Don’t miss the Witch House and the Salem Witch Trials Memorial for a touch of history (and mystery).
Unlock cheap flights for your trip
2. Rockport – The Ultimate Seaside Escape (1 hour)
Rockport is the New England postcard brought to life — colorful fishing shacks, sea breezes, and clam chowder so good you’ll want to move there.
Stroll down Bearskin Neck, a narrow street lined with art galleries, cafés, and ocean views. Snap a photo of Motif No. 1, one of the most painted buildings in America. Then, grab some fried seafood at The Lobster Pool, where you can eat with your feet practically in the water.
3. Gloucester – America’s Oldest Seaport (50 minutes)
Just next to Rockport lies Gloucester, the perfect mix of grit and charm. This town has deep fishing roots — immortalized in The Perfect Storm — but also a thriving arts scene.
Hop on a whale-watching tour (they’re some of the best on the East Coast), visit the Fishermen’s Memorial, and don’t skip Good Harbor Beach for some serious chill time.
4. Concord – Revolutionary History Meets Literary Legends (40 minutes)
Few towns pack as much history per square mile as Concord. Walk the Old North Bridge, where “the shot heard round the world” was fired, then explore Minute Man National Historical Park.
After soaking in the Revolutionary War history, switch gears and visit Louisa May Alcott’s Orchard House or Walden Pond, where Henry David Thoreau found peace (and probably some mosquito bites). Bring a picnic — Concord is made for slow afternoons.
5. Lexington – Where the Revolution Began (30 minutes)
Lexington and Concord go hand-in-hand. Start your morning at the Battle Green, where the first shots of the American Revolution were fired in 1775.
The Lexington Historical Society offers guided tours that make the events come alive. Afterward, stop by Ride Studio Café for excellent coffee and people-watching.
6. Portsmouth, New Hampshire – Waterfront Cool Meets Colonial Past (1 hour)
Cross the Massachusetts border and you’ll find Portsmouth, a small coastal city with major personality. Its cobblestone streets, boutique shops, and restaurants make it perfect for a day trip.
Grab brunch at The Friendly Toast, then wander through Strawbery Banke Museum, an outdoor history village where costumed interpreters tell stories from four centuries of New England life.
Before heading back, grab an ice cream and watch the sunset from Prescott Park — it’s pure magic.
7. Newport, Rhode Island – Mansions and Ocean Views (1.5 hours)
If you love history, glamour, and sea air, Newport is your dream day trip. The famous Newport Mansions — like The Breakers and Marble House — are jaw-dropping reminders of the Gilded Age.
Take a stroll along the Cliff Walk, where waves crash below you and mansions gleam above. Then enjoy fresh oysters at The Mooring before heading back. Newport is elegance with saltwater in its veins.
8. Plymouth – America’s Hometown (50 minutes)
Step back into 1620 in Plymouth, where the Pilgrims first landed. Sure, Plymouth Rock might be underwhelming (spoiler: it’s smaller than you expect), but the Mayflower II and Plimoth Patuxet Museums make up for it.
It’s a fascinating mix of early colonial life and Wampanoag culture. After sightseeing, grab a seafood platter at Wood’s Seafood by the harbor — you’ll thank me later.
9. Cape Cod – Beach Town Bliss (1.5 hours)
Cape Cod is the ultimate summer escape. From Sandwich to Provincetown, every town has its own flavor — but for a day trip, head to Falmouth or Hyannis for easy access and plenty of beaches.
Rent a bike and ride the Shining Sea Bikeway, or catch a ferry to Martha’s Vineyard if you’re feeling adventurous. Cape Cod in 2025 is all about relaxed vibes, sea breezes, and a scoop (or two) of ice cream at Four Seas Creamery.
10. Martha’s Vineyard – An Island Adventure (2 hours via ferry)
If you start early, you can absolutely make Martha’s Vineyard a day trip. Take the ferry from Woods Hole (about 90 minutes from Boston by car) and spend the day exploring the island’s laid-back towns.
Visit Edgartown for its elegant streets and lighthouses, or head to Oak Bluffs for the colorful “gingerbread cottages.” Rent a bike or a moped — that’s how locals get around.
The island’s vibe? Coastal, charming, and just a touch bougie — in the best way.
11. Nantucket – Quiet Luxury by the Sea (2 hours + ferry)
Want something even more exclusive? Nantucket is your spot. The ferry from Hyannis will get you there in an hour, and you’ll be stepping into a postcard of gray-shingled cottages, cobblestone streets, and perfect beaches.
Wander the town, check out the Whaling Museum, and enjoy a lobster roll at Cru Nantucket — possibly the most scenic seafood spot in New England.
12. Worcester – Food, Art, and Hidden Cool (1 hour)
Don’t sleep on Worcester. This underrated city west of Boston has quietly reinvented itself as an artsy, foodie destination.
Visit the Worcester Art Museum, grab lunch at The Mercantile Rooftop Bar, and explore Canal District boutiques. In summer, Polar Park (home to the WooSox baseball team) buzzes with local energy.
13. Providence, Rhode Island – Artsy, Historic, Delicious (1 hour)
Providence has that perfect mix of Ivy League intellect and creative chaos. Start with a walk along the Riverwalk, pop into RISD Museum, and wander Benefit Street, lined with colonial-era homes.
Hungry? You’re in the right place — Providence’s food scene punches way above its size. Head to Federal Hill for Italian classics or Plant City for world-class vegan eats.
If you time it right, stay for WaterFire, an outdoor art installation where bonfires light up the river. It’s unforgettable.
14. Mount Monadnock, New Hampshire – The Best Hike Near Boston (1.5 hours)
For nature lovers, Mount Monadnock is the perfect outdoor escape. It’s one of the most climbed mountains in the world — not too tall, not too easy, and with epic summit views.
Bring hiking shoes, snacks, and water. The trail takes about 3–4 hours round trip. When you reach the top, the panorama of New England forests and lakes is pure reward.
15. Wachusett Mountain – Hike or Ski Close to Home (1 hour)
Just an hour west of Boston, Wachusett Mountain is a year-round favorite. In summer, it’s all about hiking and scenic drives; in winter, you can hit the slopes for a quick ski fix.
On your way back, stop by Wachusett Brewing Company for craft beer and local bites — the perfect post-adventure treat.
16. The Berkshires – Art, Nature, and Small-Town Soul (2 hours)
Okay, this one’s a stretch for a day trip, but totally worth it. The Berkshires are a cultural and natural wonderland in western Massachusetts.
Visit Mass MoCA for mind-bending modern art, stroll through Stockbridge (Norman Rockwell’s hometown), or hike Monument Mountain for sweeping views.
If you’re visiting in summer, don’t miss a concert at Tanglewood, the Boston Symphony Orchestra’s stunning outdoor venue.
17. Portland, Maine – Foodie Heaven by the Sea (2 hours)
Last but definitely not least: Portland. This small coastal city is New England’s ultimate foodie paradise.
Grab lobster rolls at Eventide Oyster Co., browse boutiques in the Old Port, and wander along the working harbor where fishermen still haul in the day’s catch.
If you’re into craft beer, Portland’s scene is legendary — with standouts like Allagash and Bissell Brothers. It’s laid-back, artsy, and endlessly walkable.
🚗 Getting Around – Car, Train, or Ferry?
- By Car: Most of these trips are easiest by car, especially Cape Cod, the Berkshires, and New Hampshire.
- By Train: Salem, Worcester, and Providence are simple train rides from South Station or North Station.
- By Ferry: For islands like Martha’s Vineyard or Nantucket, catch the ferry from Woods Hole or Hyannis.
✨ Final Thoughts: So Many Adventures, So Little Time
Living near Boston means being spoiled for choice — beaches, mountains, islands, and history all within a few hours. Whether you’re chasing fall colors, summer sunshine, or cozy winter towns, New England delivers in every season.
So next time you’ve got a free Saturday, grab your keys (or train ticket), cue up your road-trip playlist, and head out. The best of New England is waiting just beyond the city skyline — and trust me, you’ll never run out of amazing Boston day trips to take. 🌲🚗✨
