25 Best Day Trips from Boston, MA: Local’s Guide (2026)

Growing up just outside of the city,  I like to think I have perfected the art of day trips from Boston, MA. While the city itself is wonderful, it can be nice to hop in the car and explore a bit further out. Particularly in nicer weather, a day trip is just what the doctor ordered! 

From the North Shore to the South Shore and a bit further out, here are some of the best day trips from Boston, MA!

Editor’s note: Sara wrote the original version of this article and her North Shore, South Shore, Cape Cod, and Ogunquit recommendations are preserved throughout. I’ve added new destinations and farther New England escapes from my own experience growing up in Boston. Anywhere you see Sara’s name attached, those are her firsthand picks. Everything else is mine. – Eileen

Jump to a section

Quick day trips (under 90 minutes)

• Rockport, MA
• Gloucester and Cape Ann, MA
• Newburyport, MA
• Salem, MA
• Concord, MA
• Lexington, MA
• Hingham and the South Shore, MA
• Plymouth, MA

Half-day to full-day trips (90 min to 2 hours)

• Cape Cod (Outer Cape and beyond)
• Provincetown, MA
• Mid Cape (Hyannis, Yarmouth, Dennis)
• Newport, RI
• Ogunquit, ME
• Portsmouth, NH
• Kennebunkport, ME

Farther afield (2-3+ hours, day or weekend)

• The Berkshires and Tanglewood
• Mystic, CT
• Portland, ME
• North Conway, NH
• Camden, ME
• Stowe, VT

Plan your day trip

• How to choose your day trip

1. Rockport, MA

Sara’s pick

Looking to go for a gorgeous drive with a pit stop or two along the way? The Essex Coastal Scenic Byway is a 90-mile roadway connecting Massachusetts communities like Rockport, Gloucester, Manchester-by-the-Sea, and Salem.

Each town has its own unique history and selling points, but Rockport is one you certainly won’t want to skip. One of the first sights you’ll see is Motif No. 1, the red fishing pier that’s a Rockport staple. Fun fact: it’s the most painted building in the world. You’ll definitely want to snap a few photos.

Sandy Bay’s Front Beach is open to visitors and locals year-round, and is a quick walk from downtown. The downtown village is known for its eateries like Roy Moore Lobster Company, and you can finish off your meal at Rockport Brewing Company. When looking for a sweet treat, The Ice Cream Store on the water is super popular for good reason.

Drive time from Boston: ~1 hour Car required: Yes (or commuter rail to Rockport station)

2. Gloucester and Cape Ann, MA

Gloucester sits right next to Rockport on Cape Ann and deserves its own day. It’s America’s oldest continuously operating fishing port, dating back to 1623, and the working harbor character is part of the appeal. Don’t miss the iconic Fisherman’s Memorial statue (“They That Go Down to the Sea in Ships”), Good Harbor Beach for one of the best North Shore swimming beaches, and the Cape Ann Museum for the maritime history and Fitz Henry Lane paintings.

For lunch, The Causeway is a local-favorite for huge plates of fresh seafood, and Sugar Magnolias does excellent breakfast.

Gloucester also has one of the most reliable whale watching scenes in New England. Capt. Bill & Sons Whale Watch and 7 Seas Whale Watch both run trips from spring through fall, with very high success rates of spotting humpbacks and minke whales.

Drive time from Boston: ~45 minutes Car required: Yes (or commuter rail to Gloucester station)

3. Newburyport, MA

Sara’s pick

Newburyport is also within the Essex Coastal Scenic Byway, but it deserves to be one of its own day trips from Boston. It’s home to Plum Island, an adorable area off the coast of Cape Ann. Take Instagram-worthy pictures of the lighthouse, then make your way to one of the stunning state parks or trails.

The Parker River National Wildlife Refuge is a refreshing gem in Newburyport. Established in 1941 as a nesting habitat for migratory birds, you’ll find sandy dunes, cranberry bog, and freshwater marsh. It’s the best spot for photography in the area.

Maudslay State Park is also a breathtaking natural landscape with 19th century gardens. Take a leisurely walk or rent a bike. If you’re a MA resident, the parking fee is only $5, so make a day of it.

Once walking has you worn out, grab a pint from Newburyport Brewing Co. After all, the best day trips end up at a local brewery.

Drive time from Boston: ~45 minutes Car required: Yes (or commuter rail to Newburyport station)

4. Salem, MA

Salem is the witch trial capital of the country and one of the most popular day trips from Boston for good reason. It’s also the kind of place that gets very different depending on when you go. October is peak Halloween mecca, and the city goes all in with witch tours, haunted attractions, and crowds you’ll need to plan around. Off-season Salem is much quieter and arguably more interesting if you actually want to learn the history.

Don’t miss the Salem Witch Museum for the foundational history of the 1692 trials, the Witch House (the only structure with direct ties to the trials still standing), and the Salem Maritime National Historic Site on the waterfront. The Peabody Essex Museum is one of the oldest continuously operating museums in the country and worth a couple of hours.

For food, Turner’s Seafood at Lyceum Hall is the local-favorite for fresh New England seafood in a historic building (Alexander Graham Bell made the first long-distance phone call from this room). Gulu-Gulu Cafe is a great low-key lunch spot.

Drive time from Boston: ~30-40 minutes Car required: No (commuter rail to Salem station, easy walk to downtown)

5. Concord, MA

Concord is one of my favorite small-town day trips from Boston, especially in fall when the foliage hits and the historic homes look like a movie set. The town packs in an extraordinary amount of American history and literary heritage in a very walkable downtown.

Walden Pond is the obvious must-do. You can walk the perimeter (about 1.7 miles), swim in summer, and visit the replica of Thoreau’s cabin. Get there early on summer weekends because parking fills up.

The Old North Bridge at Minute Man National Historical Park is where the “shot heard ’round the world” was fired in 1775. The bridge and the surrounding park are free, and it’s a meaningful stop even if you’re not a history buff.

For the literary lovers: the Louisa May Alcott Orchard House is the home where “Little Women” was written, and it’s preserved beautifully. Ralph Waldo Emerson’s house and Henry David Thoreau’s birthplace are both nearby too.

Downtown Concord has lovely shops, the iconic Concord Bookshop, and great coffee at Haute Coffee. For lunch, Woods Hill Table is a farm-to-table standout.

Drive time from Boston: ~30 minutes Car required: Helpful but not strictly necessary (commuter rail to Concord station)

6. Lexington, MA

Lexington pairs naturally with Concord (you can do both in a day if you start early). The Battle Green is where the Revolutionary War began on April 19, 1775, and the surrounding area has preserved homes, tavern, and memorials from that era.

The Lexington Visitor Center is a good starting point with maps and self-guided tour information. From there, walk the Battle Green, visit Buckman Tavern (where the colonial militia gathered before the battle), and the Hancock-Clarke House (where John Hancock and Samuel Adams were staying when Paul Revere rode in to warn them).

If you’re in town on Patriots’ Day (the third Monday in April), the Battle Green hosts an early-morning reenactment of the battle starting around 5:30 AM. It’s a Massachusetts tradition.

For food, Via Lago is the longtime local pick for an upscale lunch or dinner.

Drive time from Boston: ~25 minutes Car required: Yes (or bus from Alewife Red Line station)

7. Hingham and the South Shore, MA

Hingham section by Sara, additional South Shore picks by Eileen

The South Shore is beween Boston and Cape Cod, mostly along the coastline. While it’s not necessarily a destination region, if you’e road tripping or looking to experience small town charm, there’s some great areas to check out (and lots of food!)

Scituate and Cohassett are farther off the highway (Route 3), but have some of the prettiest ocean and harbor views. In Scituate, grab a cone from Dribbles (an iconic ice cream shop) or indulge in a salt spa afternoon a the Scituate Salt Cave. You might find the cutest coffee shop around at Lucky Finn too.

Norwell is a small farm town closer as a pit stop, but Hornstra Farms has the BEST ice cream around. I don’t say that lightly! If you’re a big fan, have a treat and visit the baby cows in the barn too. Nearby is Wompatuck State Park if you want to get out and stretch your legs.

Hingham (Sara’s pick):

Hingham is a cute little town with a colonial feel, settled on the waterfront of Boston Harbor. There are lots of things to do, and one of the most popular is to visit the Derby Street Shops, an upscale outdoor outlet area with stores like Anthropologie, J Crew, and Lululemon.

World’s End park is also a tourist favorite, offering sweeping views of the Boston skyline. The landscape was designed by the famous Frederick Law Olmsted, so the trails are top-notch.

Main Street is a fun stretch of cafes, restaurants, boutiques, and an old-timey movie theatre. Brewed Awakenings is one of Sara’s all-time favorite coffee spots, with an extensive menu and selection of pastries. If you end up in Hingham around dinner time, check out Alma Nove, a waterfront restaurant inspired by flavors from Italy and the Mediterranean (and yes, named after the Wahlberg family matriarch).

Drive time from Boston: ~30 minutes Car required: Helpful (or MBTA ferry from Long Wharf to Hingham, a lovely ride)

8. Plymouth, MA

Sara’s original pick, expanded with Eileen’s local notes

Many tourists travel to Plymouth with eager anticipation to see Plymouth Rock. And while that experience is a bit underwhelming (the rock is small and behind a fence), the town still has a lot to offer.

This coastal town is acclaimed for its seafood restaurants like Cabby Shack right by the harbor. There’s also KKatie’s Burger Bar for a casual life-changing burger, or East Bay Grille for an upscale, classic New England dining experience.

There’s a jetty right on the Plymouth Harbor for a nice stroll. Of course, if you’re looking to immerse yourself in history, you’ll want to visit Plimoth Patuxet (recently renamed from Plimoth Plantation). The recreation of the pilgrim’s original settlement is a fun and interactive way to learn the rich history of the town.

For the full Plymouth treatment with all my local picks (breweries, beaches, the historic sites in order, restaurants beyond the harbor), see my full guide: Things to Do in Plymouth, MA: A Local’s Guide.

Drive time from Boston: ~45 minutes to 1 hour Car required: Helpful (or commuter rail to Plymouth station)

If you’re a true city dweller and don’t own a car, renting a car for a day is a great way to escape the city for a little while, especially for these farther out destinations below!

9. Cape Cod (the basics)

Sara’s pick, expanded by Eileen

One of the most beloved day trips from Boston is a day spent on the Cape. There are multiple regions worth checking out:

• Upper Cape: Falmouth, Mashpee, Sandwich, Bourne
• Mid Cape: Dennis, Yarmouth, Barnstable, Hyannis
• Lower Cape: Brewster, Chatham, Harwich, Orleans
• Outer Cape: Eastham, Wellfleet, Truro, Provincetown

Sara recommends the Outer Cape for a day trip, as it feels more separated from the busier towns. I agree, but I’ve covered Mid Cape separately below for travelers who want easier logistics. Cape Cod traffic in summer is real, especially on Friday afternoons heading down and Sunday evenings coming back, so plan accordingly.

Drive time from Boston: 1.5-2.5 hours depending on destination and traffic

10. Provincetown, MA

Sara’s pick

Provincetown, or P-town, is a trendy and popular summer destination at the very tip of Cape Cod. The vibrant town is less than a 3-hour drive from Boston, but you can also opt to take a ferry ride over from the Seaport. The ferry is pricier but offers gorgeous water views and lets you skip the Cape traffic.

Commercial Street is where all the action is. The East End is home to art galleries and the Provincetown Art Association & Museum, with great coffee stops like Wired Puppy along the way. The West End is more bustling with restaurants and shops, and colorful enough that you’ll want time to just wander.

For Eileen’s full P-town guide with restaurants, beaches, where to stay, and how to handle the ferry vs drive decision, see Plan for P-Town: 24 Hours in Provincetown, Massachusetts.

Drive time from Boston: ~2-2.5 hours (or 90-min ferry from Seaport)

11. Mid Cape (Hyannis, Yarmouth, Dennis)

If the full P-Town trip feels like too much for a day, Mid Cape is the more manageable option and an underrated day trip. Hyannis is the gateway, with the JFK Hyannis Museum, Kalmus Beach for windsurfing, and ferries to Nantucket and Martha’s Vineyard if you want to fold in a half-day island detour.

Yarmouth and Dennis are quieter with classic Cape beaches. West Dennis Beach is a personal favorite for families because the parking is easy and the water is shallow and calm. The Cape Cod Rail Trail runs through this area and is excellent for a casual bike ride.

For food: The Naked Oyster in Hyannis is a local favorite. The Friendly Fisherman in Eastham is a no-frills seafood spot worth the drive too.

Drive time from Boston: ~90 minutes to 2 hours

12. Newport, RI

Newport sits in Rhode Island but is genuinely one of the easiest and best day trips from Boston, just 90 minutes south. The Gilded Age mansions (The Breakers, Marble House, The Elms) are the obvious draws, plus the Cliff Walk for the free coastal stroll past the mansions. Ocean Drive is the 10-mile loop you’d be silly to skip.

For my full Newport guide with where to stay if you want to extend to an overnight, the spa picks, the food scene, and the bachelorette angle, see Newport RI Girls Trip: The Ultimate Off-Season Getaway Guide.

Drive time from Boston: ~90 minutes via I-93 South and Route 24 Car required: Yes (no direct train to Newport)

13. Ogunquit, ME

Sara’s pick

About a 2-hour drive from the city, high on Sara’s list of day trips from Boston is Ogunquit, Maine. On the southern coast of Maine, Ogunquit’s motto is “beautiful place by the sea.”

The Cliff House Resort and Spa is one of the most gorgeous hotels Sara has ever stayed at. Nautical decor adorns the lobby and rooms. The amenities aren’t too shabby either, with an indoor pool and two outdoors, a luxury spa, and access to Cape Neddick Golf Club.

Be sure to include a walk along Marginal Way on your day trip itinerary. This coastal path keeps you right near the water, and will land you in the adorable Perkins Cove area, where there are many eateries overlooking the ocean. Jackie’s Too is a Sara favorite.

If you want to extend Ogunquit into a longer trip up the Maine coast, see Eileen’s Boston to Maine Road Trip itinerary.

Drive time from Boston: ~75-90 minutes

14. Portsmouth, NH

Portsmouth is the most charming colonial seaport in New England and a genuinely lovely day trip. It’s small enough to cover on foot, packed with restored colonial homes (the Strawbery Banke Museum is the standout), great independent shops, and one of the best small-city food scenes north of Boston.

Don’t miss Market Square for the heart of downtown, Prescott Park in summer for free concerts and gardens on the waterfront, and a walk across the Memorial Bridge to Kittery, Maine (with the famous Kittery outlets if you want to fold in shopping).

For food: Black Trumpet for an upscale dinner, The Friendly Toast for funky brunch, Stoneface Brewing for craft beer.

Drive time from Boston: ~1 hour Car required: Helpful (or C&J Trailways bus from South Station)

15. Kennebunkport, ME

Kennebunkport is the storybook Maine coastal town with the Bush family compound, classic harbor views, and one of the prettiest downtowns in New England. Dock Square is the heart of it, with shops, restaurants, and the Colony Beach nearby. The Captain Lord Mansion is the iconic B&B if you ever want to extend to an overnight.

For lobster, Mabel’s Lobster Claw is the long-standing local favorite, and Lobster Pier is a more casual roadside option.

Kennebunkport pairs naturally with Ogunquit on a longer Maine day. For the full Maine road trip itinerary with Kennebunkport, Ogunquit, Portland, and Freeport, see Boston to Maine Road Trip.

Drive time from Boston: ~90 minutes

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Farther afield: weekend trips and longer day adventures

The picks below stretch the definition of “day trip.” Some of you will absolutely drive 2.5-3 hours each way and call it a day (I respect you). For others, these work better as weekend escapes. Either way, they’re worth your time and they’re some of New England’s best.

16. The Berkshires (Stockbridge, Lenox, Great Barrington)

Western Massachusetts feels like a different state once you’re there: rolling hills, art galleries, and small towns that lean creative and outdoorsy. Stockbridge is the Norman Rockwell town, with the Norman Rockwell Museum preserving his studio and over 1,000 of his works. Lenox is home to Tanglewood, the summer home of the Boston Symphony Orchestra and one of the great outdoor concert venues in the country. Great Barrington has the best food scene and a thriving art gallery district.

Other Berkshire musts: MASS MoCA in North Adams (one of the largest contemporary art museums in the country, in a renovated factory complex), and the Clark Art Institute in Williamstown.

Drive time from Boston: ~2.5 hours Works as: Long day trip in summer for Tanglewood, otherwise weekend trip

17. Mystic, CT

Mystic is a perfect family day trip and one of the most-visited coastal Connecticut towns. The Mystic Seaport Museum is one of the country’s largest maritime museums, with restored 19th-century sailing ships you can board. The Mystic Aquarium has beluga whales, African penguins, and a strong reputation. Downtown Mystic itself is small and walkable, with shops and the iconic drawbridge.

Yes, this is the town from the movie “Mystic Pizza.” Yes, the restaurant exists and is still there.

Drive time from Boston: ~2 hours

18. Portland, ME

Portland has become one of the best food cities in the country in the last decade and works as either a long day trip or a weekend. Old Port is the historic downtown with cobblestones, breweries (Allagash, Bissell Brothers), and excellent restaurants (Scales for seafood, Eventide Oyster Co. for, well, oysters). Portland Head Light is one of the most photographed lighthouses in America and a quick drive from downtown.

The full Portland breakdown with hotels, restaurants, and a 24-48 hour itinerary is in my Weekend for 30-Somethings in Portland, Maine guide, and Portland is also the headline stop on my Boston to Maine Road Trip.

Drive time from Boston: ~2 hours Train option: Amtrak Downeaster from North Station (~2.5 hours)

19. North Conway, NH

North Conway is in the heart of the White Mountains and a great year-round escape. Skiing and snowboarding at Cranmore in winter, hiking and the Mount Washington Cog Railway in summer, leaf-peeping in fall, and the Settlers Green outlet shopping for any season. Storyland for families with young kids is a classic.

The drive itself is part of the appeal: Route 16 through the Notch is one of the prettiest in the country, especially in fall.

For the full North Conway breakdown including where to stay, see my A Cozy Escape: Your Guide to North Conway, NH guide.

Drive time from Boston: ~2.5-3 hours Works as: Long day trip for skiers, weekend trip for everyone else

20. Camden, ME

Camden is mid-coast Maine and a real stretch for a day trip from Boston, but it’s such a beautiful town that some people do it. Most don’t, and that’s the right call most of the time. Better as part of a longer Maine coast trip.

If you do go for a day: take a windjammer sail on the historic Schooner Surprise, hike Mount Battie for the view that inspired Edna St. Vincent Millay’s “Renascence,” and eat at Camden Deli on the harbor.

For the full Camden experience, see Camden, Maine’s Delights During Shoulder Seasons.

Drive time from Boston: ~3-3.5 hours Works as: Weekend trip

21. Stowe, VT

Stowe is at the outer edge of what counts as a “day trip” from Boston, but I’m including it for the Stowe fans (you know who you are). Quintessential Vermont mountain town with skiing in winter, hiking and Ben & Jerry’s factory tours in summer, and foliage that hits hard in late September and early October.

For the full Stowe experience, see Embracing Joy: An Ode to Stowe, Vermont.

Drive time from Boston: ~3 hours Works as: Weekend trip, not a day trip

A few more quick mentions

22. Cape Ann’s Manchester-by-the-Sea for the prettiest small beach town on the Essex Coastal Scenic Byway (yes, it’s the town from the movie). Singing Beach is genuinely one of the best beaches on the North Shore.

23. Marblehead, MA for sailing history, a charming downtown, and Castle Rock for views back across the harbor toward Boston.

24. Worcester and Sturbridge, MA for the Worcester Art Museum, the Sturbridge Village historical site, and an under-the-radar New England weekend. Here’s the full breakdown: Worcester and Central Massachusetts for a Weekend.

25. Block Island, RI for a day-trip-with-a-ferry adventure. Drive to Point Judith in Rhode Island (about 90 minutes), then take the high-speed ferry (~30 minutes). The island is bike-friendly with stunning coastline.

How to choose your day trip from Boston

A few quick filters to help you pick:

Going with kids? Plymouth, Hingham, Mid Cape, Mystic, and Concord/Lexington all skew family-friendly with easy logistics and kid-targeted attractions.

Want the beach? Cape Cod, Cape Ann (Gloucester/Rockport), Ogunquit, and the South Shore are your best bets in summer.

Going for history? Salem, Concord, Lexington, Plymouth, Portsmouth, and Newport all deliver strong colonial and Revolutionary-era history.

Going in fall for foliage? The Berkshires, North Conway, Stowe, and Concord (which is gorgeous and walkable in October).

Going without a car? Salem, Plymouth, Hingham (via commuter rail), Newburyport, and Portsmouth are all reachable by commuter rail or bus. The rest will require a car.

Renting a car vs. taking the train

Most of the day trips on this list are easier with a car, but several work well via public transit:

Commuter rail (cheap and easy):

• Salem (Rockport Line)
• Rockport (Rockport Line)
• Gloucester (Rockport Line)
• Newburyport (Newburyport Line)
• Concord (Fitchburg Line)
• Plymouth (Plymouth/Kingston Line, with some logistics)

Bus:

• Portsmouth NH (C&J Trailways from South Station)
• Cape Cod (Plymouth & Brockton Bus from South Station)
• Provincetown (Bay State Cruise Co or Boston Harbor Cruises ferry from Seaport, summer only)

Amtrak:

• Portland ME (Downeaster from North Station)

Ferry:

• Provincetown (seasonal, Seaport)
• Hingham (MBTA ferry from Long Wharf, year-round)

For everywhere else, renting a car for the day is the move. The Cape, the Berkshires, Mystic, Newport, the Maine coast beyond Portland, North Conway, Stowe, all require driving.

Read more New England travel guides

• Things to Do in Plymouth, MA: A Local’s Guide
• Newport RI Girls Trip: The Ultimate Off-Season Getaway Guide
• Boston to Maine Road Trip: The Complete Itinerary
• A Cozy Escape: Your Guide to North Conway, NH
• Embracing Joy: An Ode to Stowe, Vermont
• Plan for P-Town: 24 Hours in Provincetown
• Camden, Maine’s Delights During Shoulder Seasons
• Worcester and Central Massachusetts for a Weekend
• Girls Weekend in Boston: A Local’s Neighborhood Guide
• 25+ Best Things to Do in Boston, MA: A Local’s Guide
• Travel to New England: A Local’s Guide

Do you prefer the North Shore or South Shore? What’s your favorite town on Cape Cod? What is your ideal day trip in Massachusetts?

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