Boston is well worth a visit, and there’s plenty to keep you busy in the largest city in New England, but you’d be missing out if you didn’t explore some of the fun day trips from Boston! From coastal towns to cute mountain towns, you really can’t miss these.
I spent a couple of semesters in Boston during college and absolutely fell in love with it. I was able to explore the entire area and really can’t say enough good things about it! Here are some amazing day trips to consider on your next trip to Boston.
Table of Contents
P.S. – In this post, I’ll give you guidance on getting to each place with or without a car. I’ll include guided options and DIY options, too. I’ve got you, no matter what type of trip you’re taking!
We’ll start with the closest day trips and work to the futhest on this list.
Tips & Planning Ahead
- Vermont in the fall
- Boston to Portland, ME or Acadia National Park
- Boston to NYC or Washington, DC
- Coastal New England
Driving in New England
In general, driving in New England is pretty easy if you’re used to city driving! As someone who grew up in Texas, I found the driving around Boston challenging at first, but I was able to adjust. Once outside Boston, it’s much easier.
Why was that? People use their horns here more often, and they are more aggressive than I was used to.
Parking can be a challenge on many of the day trips on this list because many were established before cars and are historic areas. These historic areas are protected, and there are a few parking garages. Be prepared to pay for parking or to walk long distances to major sites, potentially.
You’ll also need to be ready for toll roads with different pay stations throughout New England and plenty of roundabouts! If you plan to rent a car, I suggest including the daily toll pass in your rental if you’re taking multiple day trips.
None of these things is too much to handle; you’ll be fine, but it’s good to know about them before your drive.
Public Transit from Boston
If you don’t want to drive, you’ll find that most of the day trips on this list will still be accessible! The East Coast has great public transit, but New England is especially connected, and Boston is right at the center of the public transit.
There are two main public transit options to know about, both helpful for day trips. I’ll point them out throughout this post and explain where they can be accessed. They are outlined below:
- MBTA or the T, as locals call it! This is the Boston area transit system and commuter rail that will take you to many places around Boston, even an hour or more away from the city.
- Amtrak: The national passenger railroad corporation of the United States, a federally supported company that operates most of the country’s intercity rail passenger service. The available stops in New England are fairly extensive compared to other parts of the US.
There’s also a crossover between MBTA and Amtrak stops. I’ll note those at the very end of each section for each town on the list.
Day Trips from Boston in Massachusetts
There are plenty of amazing day trips in Massachusetts worth a visit. This state is full of historic places, great beaches, and many places you’d be surprised you have (likely) heard of but maybe didn’t even realize were in the state!
Salem
Salem is known for the Salem Witch Trials and can get extremely crowded during the fall, but it’s great to explore no matter the season! Downtown Salem is really charming, with a harbor and many unique shops to explore. It’s one of the easiest day trips from Boston on this list.
I’ll be the first to admit that Salem is one of those towns that feels pretty touristy to me, but if you’ve never been before, it’s well worth going to! It’s one of the most popular day trips from Boston, and if you’re visiting, I highly recommend booking a walking tour while there to learn the history.
While here, make sure you:
- Visit one of the museums about the history of Salem, like the Salem Witch Museum, the House of Seven Gables, or the Witch House. Stop by the Bewitched Statue
- Grab some unique souvenirs in the shops on Essex Street.
Pro tip: If you visit in the fall, expect to struggle to find parking here. Salem is one of the most famous places to visit on Halloween. Be very careful of street parking, as there are many rules to save the parking spaces for locals (as they should!).
Accessible on the T from Boston, 35 minute drive
Tour option: Salem Witch Trials History Tour
Ipswich
This cute seaside town is along the north shore of Massachusetts. The drive between Rockport and Ipswich is a beautiful coastal drive you’ll love! I recommend driving this one and combining it with a few other coastal towns on the list, like Rockport and Newburyport.
Ipswich is a great stop for those who want to explore the outdoors and history. You’ll find beautiful coastal views here, and while it has a cute, historic downtown, my favorite things to do are on the outskirts!
While here, make sure you:
- Visit Crane Estate and explore the views from Castle Hill; there’s also a great beach here
- Hike or canoe along the river or explore the marshes
- Visit a historic working farm like Appleton or Russell Orchard
- Explore historic homes and walk through the downtown area
Image by Anne and Saturnino Miranda from Pixabay
Rockport
Downtown Rockport is probably one of the most iconic coastal New England towns, famous for Motif #1 – one of the most painted and photographed structures in the world. The charm that the port here has is quintessential New England.
I remember having the best clam chowder (a New England classic) of my life at the port and just taking in the calm as the sun began to set. I wish I remembered where, but that was 15 years ago! If you visit today, I’m sure you’ll still find great clam chowder.
While in Rockport, don’t miss:
- Exploring some of the 30+ art galleries in town
- Visiting the harbor for amazing lobster or clam chowder
- Relaxing on the beach, consider Long Beach, Cape Hedge Beach, and Front Beach
Accessible on the T from Boston, 1 hour drive
Newburyport
Newburyport is a charming coastal town with a small-town feel and plenty of things to do. If you want some history and great boutique shopping, you’ll love it here. If you want a lovely beach and coastal activities, again, you’ll love it here!
This is a stop you could easily spend an entire weekend at, but if you only have a few hours, it’s still worth a stop. I’m sad I didn’t get to revisit on my last trip, as I love this charming town.
Things you don’t miss in Newburyport:
- Rent bikes from Port Bikes or electric bikes from EZ Pedlar and enjoy a ride along the coast or on the Clipper City Rail Trail
- Visit Plum Island for some beach time
- Shop in Tannery Historic Marketplace, a hub of independent shops and boutiques
Accessible on the T or Amtrak from Boston, 46 minute drive
Plymouth
This may be another touristy stop, but if you’re interested in early colonial history, a day trip to Plymouth still has plenty to offer! I’ll tell you right off the bat that Plymouth Rock itself is a big disappointment. It’s actually really small, and they aren’t even sure it’s the original rock!
All that being said, there are fun things to do on a day trip to Plymouth. Plymouth is known as the first European settlement in New England, so the sites here are focused on that early history, and it has plenty of historic charm to discover!
Here are a few highlights:
- Shop for antiques and eat in the picturesque downtown
- Visiting Plimoth Patuxet Museums, a world-renowned living history museum
- See artifacts from the Mayflower and explore the oldest continuously operating public museum in the US, Pilgrim Hall Museum
Accessible on the T from Boston, 1 hour drive
Tour option: Cape Cod and Plymouth Day Tour
Cape Cod
A classic area to visit from Boston is Cape Cod. The star of this day trip is the many beaches that line both sides of Massachusetts’ Cape, but there are plenty of other great things to do here.
I think Cape Cod is a summer New England classic, but it can be great during shoulder season too. I’ve been in every season and I can tell you, it’s still worth a visit if you want some history and picturesque towns. The only time of year I wouldn’t visit is winter – many things close up and it gets very cold there!
Highlights of visiting Cape Cod:
- Visit the Cape Cod chip factory – see how chips are made and get a free bag! Bonus: Nauset Lighthouse is close by, so make a stop there, too
- Learn about Cape history in Sandwich at Hoxie House, the oldest house on Cape Cod, and make a stop at the Sandwich Glass Museum
- Hit some cute beach towns like Provincetown (easiest without a car), Falmouth, or Harwich Port
- Relax on the beach at the Cape Cod National Seashore
Accessible via drive (can be 2-3 hours during peak season and traffic), ferry to Provincetown from Boston in 90 min, train service during weekends in summer via the CapeFlyer
Pro-tips: Plan to leave as early as you can to ensure you don’t hit much traffic if you’re driving. You can also easily combine Cape Cod and Plymouth if you have more than a day to explore as Plymouth is on the way to Cape Cod.
Tour option: Cape Cod and Plymouth Day Tour
Photo by Aubrey Odom on Unsplash
Martha’s Vineyard
Another summer classic New England spot that is accessible from Boston via day trip is Martha’s Vineyard. This is the farthest destination in Massachusetts on the list, but it is stunning! You’ll want to be prepared for a long travel day if you decide on this day trip.
Martha’s Vineyard is an island about 45 minutes from the mainland of Massachusetts, known for its stunning homes, celebrity sightings, and cute coastal towns.
Ideas for Martha’s Vineyard:
- Explore Oak Bluffs for cute shops, dining, and the gingerbread houses.
- Rent a moped or bike to explore the island for the day
- Relax at Joseph Sylvia State Beach in Edgartown (Jaws fans, anyone?)
Accessible drive + ferry (roughly 1.5–2 hours to Woods Hole or Falmouth to park and board a ferry) or CapeFlyer + ferry during the summer on weekends. The ferry is approximately 45 minutes from Woods Hole.
Tour option: Martha’s Vineyard Day Trip with Optional Island Tour
Day Trips from Boston in Rhode Island
One of my favorite states in New England is Rhode Island. This small state is beautiful and has plenty to keep you busy, whether you stay for a day or longer. I remember spending a weekend in Newport for the first time and just being SO content with a drink in hand with that salty, cool harbor breeze.
Photo by Ryan Heise on Unsplash
Providence
As the capital of Rhode Island, Providence is the third-largest city in New England, with a thriving art scene and a uniquely Rhode Island feel. The waterfront is beautiful, and there’s plenty of beautiful architecture to see here!
Providence surprised me as a state capital, it’s multiple universities help give it a different feel than you’d expect. There’s more to do here than initially meets the eye.
While here, check out:
- Visit the RISD museum to see pieces from Monet and Picasso to Andy Warhol and Coco Chanel
- Explore the architecture and shops of College Hill, don’t miss Benefit Street
- Visit the Providence Athenaeum, a historical membership library once frequented by the likes of Edgar Allan Poe
Accessible via commuter train or Amtrak, 1 hour drive
Newport
Famous as the summer home to many famous families during the Gilded Age, Newport has a lot to offer beyond these famous homes. Newport packs a lot of coastal charm with a beautiful harbor, amazing seafood, and beaches that bring the best of New England summer to life.
I love Newport, it’s a personal favorite on this list, and I would highly recommend spending more than a day here if you can. I first went to Newport for the Newport Folk Festival, which is such a fun time. If you ever get the chance, well worth going!
Things you won’t want to miss in Newport:
- Walk the Cliff Walk for stunning ocean views and look at the back of the mansions (consider a tour of one, too)
- Spend time at Fort Adams State Park for some history and amazing coastal, harbor views
- Explore Downtown and Thames Street, where you’ll find amazing seafood and plenty of boutiques for great shopping
Accessible via Amtrak or MBTA Commuter Rail to Providence or Kingston and then transfer to a bus or taxi, 90 minute drive
Tour options: Breakers, Marble House, and Downtown Newport, or Breakers, Marble House Small Group Tour
Day Trips from Boston in New Hampshire
Of all the states on this list, New Hampshire is the most underrated. New Hampshire is historically home to “blue-collar” work, with many historic mills and factories that are no longer in operation. While you may not hear much about New Hampshire, the spots on this day trip list are fantastic.
Portsmouth
One of the bigger towns on this list with tons to do is Portsmouth. Portsmouth is a great stop for history lovers who want to learn more about New England while in a charming coastal town. There’s also some fun water activities here, too!
There are many history museums here, and this is a great day trip for families. Plus, amazing food! You could easily spend a weekend here just exploring. On my latest trip, we stopped for a half-day and felt we could have spent much longer.
Here are a few top things to do in Portsmouth, NH:
- Explore history at the Strawberry Banke Museum
- Shop around in Market Square, where you’ll find plenty of boutiques, shops, and restaurants with historic charm
- See the one and only mainland lighthouse in New Hampshire – Portsmouth Harbor Lighthouse.
- Take a bike tour along the coast or a harbor cruise for great views.
Accessible on the Amtrak from Boston + bus, 1 hour 10 min drive
White Mountains
The White Mountains are the perfect destination year-round, from amazing hikes with views to fall leaves and skiing in the winter, there’s really something here no matter the season!
Covering nearly a quarter of New Hampshire, these mountains offer a stunning landscape and plenty of recreational activity. If you want to experience mountains and great hikes while on a trip to Boston, there are plenty of options here.
- Drive scenic Kancamagush Highway for stunning views and waterfall stops
- Stop at Artists Bluff for a quick hike and time at Echo Lake
- Head to a ski resort for a day on the slopes
Accessible via car, 2 1/2 hour drive
Tour option: Fall Foliage Tour in the White Mountains
Day Trips from Boston in Vermont
Vermont is well known for it’s quiet small towns, amazing farm to table food, and the mountains that cover the state.
If you’re in Boston, especially in the fall or winter, then Vermont is the perfect place to get away for the day for some amazing leaf peeping. In the winter, there are lots of ski resorts to check out. Another great year round destination!
Woodstock
Home to great local farms, a quaint downtown, and plenty of good hikes, Woodstock is a great day trip from Boston! When I visited Woodstock, it truly left a smile on my face. There’s something special about a quiet, small town full of local businesses.
If you’re looking for a cute small town with a storybook-esque feel, this town is the perfect choice. It feels that way with the historic homes, farms close by, and many covered bridges around town.
Things to check out while here:
- Hike Quechee Gorge
- Sample cheese and maple syrup at Sugar Bush Farm
- Explore history at Billings Farm and Museum
- Go antiquing and vintage shopping downtown
Accessible via car, 2 hours 15 min
Pro-tip: Consider combining Woodstock and Montpelier into a day together and spend half a day in each! They are not far apart and both have their own unique feel.
Montpelier
The other town in Vermont, I think, suitable for a day trip is Montpelier. Any town further than this would be a challenge in a day, and even visiting Montpelier will be a long driving day!
Montpelier, the capital of Vermont, has some fun history to explore. It has a beautiful downtown historic area and plenty to do. I really enjoyed the local businesses here, too! So many cool and funky shops.
What to do in Montpelier:
- Visit the Capitol Building
- Spend time at the Vermont History Museum
- Hike in Hubbard Park and take in panoramic views at Castle Craig tower
- Watch a play at The Lost Nation Theater
- Sample syrups at Bragg Farm Sugar House
Accessible via Amtrak, 2 hour 45 min drive
Day Trips from Boston in Maine
If you’re looking for some coastal, quaint towns, a day trip to Maine from Boston is the perfect fit! Maine has to be one of my favorite states on the East Coast (and probably in the US).
There are so many beautiful places here, and the food is just amazing! Well worth enjoying some time in Maine on a visit to Boston.
Kittery
Known as the oldest incorporated town in Maine, Kittery has plenty of historic charm, but visiting this small town goes beyond that!
With rich maritime history, historic homes in areas like Kittery Point, and beautiful beaches, it is a great place to spend time relaxing in the summer.
Don’t miss these highlights in Kittery:
- Explore the charming downtown area of Kittery Foreside with a variety of chef-driven restaurants, local coffee shops, and boutiques
- Enjoy scenic coastal views, Kittery Harbor and Seapoint Beach are great options
- Shop at the Kittery Outlets just off Route 1
- Learn about history at two historic seaside forts, Fort Foster (now a town park with great trails and ocean views) and Fort McClary, which stood watch from the Revolution through World War I
Accessible on the Amtrak from Boston + bus, 1 hour 10 min drive
Kennebunkport
There’s no shortage of small town charm on this list (as you can tell), with Kennebunkport being the next stop! This charming small town boasts a picturesque port with plenty to keep you busy, as well as nearby beaches and wildlife preserves that offer something for everyone.
Celebrities are also known to frequent this area. During our visit, Martha Stewart was there just the day before!! We missed her by just one day… Other celebrities known to visit Kennebunkport include Seth Rogen, Sean Penn, Taylor Swift, and the Bush family, who own a compound nearby.
Fun things to do in Kennebunkport:
- Stroll through Dock Square, the historic district, and the harbor, stopping in at shops as you walk, and enjoy the views
- Take a lobster boat or whale watching tour with First Chance Whale Watch
- Drive along Ocean Avenue to see stunning, iconic coastal Maine homes with a stop at the historic St. Ann’s church for coastal views and beauty
1 hour 30 min drive
Tour options: Portland and Kennebunkport or Kennebunkport Only
Old Orchard Beach
While several places on this list include beaches (this is a coastal drive from Boston to Portland after all), Old Orchard Beach is a coastal beach town where the main attraction is, well, the beach! Seven Mile Beach means there’s plenty of space for everyone who wants to visit to get a taste of coastal Maine beach life.
The pier here is really unique and something you won’t find at most beaches (in my experience anyway!). It is close to Portland, and you could consider stopping here for a half day at the beach and then going up to Portland for your afternoon and evening.
While here, check out:
- The only beachfront amusement park in New England, Palace Playland, offering rides and classic seaside entertainment.
- Unique boardwalk and pier with music, lights, and entertainment, creating a lively summer atmosphere.
- Eat your typical New England seaside foods, including the famous Maine lobster rolls, boardwalk fries, and fried dough.
Accessible on the Amtrak from Boston, 1 hour 40 min drive
Cape Elizabeth and Portland
Our last day trip on the list is a two-stop one! Cape Elizabeth has a quaint, beautiful small-town feel, with large historic homes and a charming downtown. It’s just 15 minutes away from Portland, meaning you can easily stop here even while spending your time in Portland.
Portland is a fun city and has plenty to keep you busy for much longer than a day, but is well worth a visit either way. I always have a good time when I’m in Portland!
Don’t miss these spots:
- Visit the oldest lighthouse in Maine, Portland Head Light, an iconic landmark offering stunning coastal views from the surrounding park, which features walking paths and historic ruins
- Head to Crescent Beach State Park, a mile-long arc of sand, and a nice place to relax for a sunny afternoon
- Explore downtown Portland for funky shops and great lobster rolls
- Take a tour of the Portland Harbor
Accessible via Amtrak (Portland only), 2 hour drive
Tour options: Portland and Kennebunkport or Portland Day Trip Only
Day Trips that are 3+ Hours Each Way
Before I end this list, I want to share a few other places that you might think – oh, I see that spot is close to Boston on the map, let’s take a day trip there!
While I wouldn’t suggest these, they are possible if you’re really determined, or maybe only in the US or on the East Coast, this once, and want to make it happen.
Here are some further day trips that you could consider:
- New York, New York: 3 hours 40 minutes
- Stowe, Vermont: 3 hours 10 minutes
- Burlington, Vermont: 3 hours 20 minutes
- Nantucket, Massachusetts: 3 hours 30 minutes, 45 minute flight
- Acadia National Park: 4 hours 30 minutes
There’s so much to explore in New England and Boston makes the perfect hub for seeing many of the best places to visit. I hope these day trips from Boston have inspired you and given you plenty of ideas for your trip!
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