5 Best Day Trips From Boston for Scenic New England Getaways

by K.C. Dermody
Updated October 02, 2023

Photo: Aubrey Odom

While it may be small in size, Massachusetts is big when it comes to diversity. It’s home to exciting cities like Boston (the largest city in New England), picturesque islands like Martha’s Vineyard, famously beautiful Cape Cod, and the rolling hills of the Berkshires.

There’s a long list of things to see and do in Boston, from historic sites and modern museums to gardens, baseball games at Fenway Park, and brewery tours. But you’re doing yourself a disservice if you spend all your time in New England in the city, since the state is so darn beautiful. Sure, take time to see the sights in Boston, but plan for at least one day trip while you’re there, too.

There are some fantastic Boston day trips within easy reach no matter what you’re idea of fun is. You’ll find everything from small-town seaside getaways to wooded inland towns – and don’t forget about famously spooky Salem.

Related: 7 Spectacular Weekend Road Trips from Boston, Massachusetts

5 Best Day Trips from Boston

1. Provincetown, Massachusetts

Provincetown, Cape Cod
Photo: Denis Tangney Jr.

Provincetown, dotted with sandy beaches, lighthouses, and wild cranberry bogs, is very doable drive from Boston for a day. The seaside town has a colorful personality that makes it a wonderful place to stroll for a morning, with everything from gorgeous mansions to bookstores, art galleries, seafood shacks, and fudge shops.

You can bring a picnic and find plenty of places to enjoy it outdoors, but if you want to stop by a restaurant, The Canteen is the best spot for delicious affordable eats (including amazing lobster rolls) in a casual beachside atmosphere.

day trips from boston
Photo: Denis Tangney Jr.

You’ll also want to spend a morning or afternoon at the Cape Cod National Seashore, which stretches for more than 40 miles between Provincetown and Chatham along the Atlantic-facing eastern shore. It’s the perfect place for a stroll on the sand, passing by tidal flats, ponds, salt marshes, and vernal pools – though adventurous types will have fun trying to scale the sand dunes. There are self-guided trails for walking and biking, along with many other recreational activities like kayak tours or surf lessons.

Provincetown is also a popular departure point for whale watching tours, so if you’re keen to listen for a blowhole or two, book a tour in advance. The ocean here is home to fin and humpback whales, regularly spotted between April and October. You might even see the extremely rare North Atlantic right whale, as Cape Cod Bay is an important breeding ground.

Whale watching boats leave from Provincetown Marina, the MacMillan Pier, and Provincetown Harbor. Dolphin Fleet is one of the more popular companies and has a ticket office at the Provincetown Chamber of Commerce (near MacMillan Pier.)

If you’re up for photographing some New England lighthouses, head to the beach around sunset. The area’s powerful winds and sandbars led to many wrecks off Provincetown’s coast, resulting in the construction of three lighthouses here. Race Point Light Station is open year-round. The original tower was first illuminated in 1816, though the current tower was built in 1876. It stands 45 feet tall and includes an adjacent keeper’s house you can book for overnight stays during the spring, summer, and fall.

The other two lighthouses, Long Point Light and Wood End Light, aren’t open to the public, but if you’re here on a foggy day, you’ll hear the eerie sound of Long Point Light’s fog horn booming in the distance.

Race Point Light Lighthouse, Cape Cod

Distance from Boston: 115 miles (approx. 2 hours)

Related read: Boston to Bar Harbor: An Essential New England Road Trip

2. Salem, Massachusetts

day trips from boston
Photo: Daniel Hanscom

Salem may be close enough that it’s practically a suburb of Boston, but it offers plenty to fill a day (and then some.) Known as the “Witch City” thanks to the infamous Salem Witch Trials (spoiler alert: they probably weren’t witches), there are lots of witch-related attractions to entertain tourists – but there’s a lot more to the city.

One of the best ways to start your visit is by learning about the city’s fascinating early history. The Salem Witch Museum tells the story of the trials here in the late 17th century through exhibits and historical presentations. And yes, there’s a Witch Museum Store in case you need to buy some friends back home a quirky or macabre souvenir.

If you’re fascinated by Salem’s witch history, be sure to also visit the Old Burying Point Cemetery, where many notable people are buried. That including the judge John Hathorne, who presided over the witch trials, and accused (and hanged) witch Martha Corey.

For some history that isn’t quite as related to witches and torture, visit the Peabody Essex Museum. It> dates  1799, making it the oldest continuously operating museum in the country. It opened when museums were known as keepers of the quirky and weird rather than being places for educational betterment. It got its start when a group of sea captains founded the East India Marine Society to collect marine specimens. However, it’s grown to hold some 1.8 million pieces of maritime, Oceanic, Asian, Indian, and African art, plus 24 historic buildings that span three centuries.

day trips from boston
Photo: iStock

If you’re a literature fan, you’ll know Salem has quite the reputation: it’s the birthplace and home of Nathaniel Hawthorne, who wrote “The Scarlet Letter” and “The House of the Seven Gables,” among others.

The historic timber-framed house known as the House of the Seven Gables was the setting for the latter. A national historic landmark dating back to 1668, it’s open for tours and provides an outstanding glimpse at what life was like during the city’s early days. Without a doubt, Salem is one of the best day trip from Boston if you like quirky, niche segments of American history (or just want to spot a ghost.)

Distance from Boston: 22 miles (approx. 40 mins)

3. Plymouth, Massachusetts

day trips from boston
Photo: iStock

Plymouth, founded in 1620, is mostly famous for being the landing site of the Pilgrims. So as you might imagine, there are multiple attractions related to the early settlers and their lives here. It’s one of the best day trips from Boston if you’re obsessed with America’s early history.

day trips from boston
Photo: Kentaro Toma

Plymouth Rock is said to mark the spot where the Pilgrims’ first touched down on the “new world” while sailing on the Mayflower. Some question if it was really where the those first settlers actually disembarked, but nevertheless, the rock still is of paramount importance to the state. It’s ensconced in a granite canopy, inscribed with “1620,” the year they landed. It’s worth the short visit just to appreciate standing in a historically significant spot for a few moments.

If Plymouth Rock isn’t enough for you, hop aboard a nearby full-scale replica of the Mayflower, which includes exhibits and tours led by costumed guides. It’d quite a fun spot, especially as the performers seem like they just walked off the ship themselves as they share historical stories and tales.

Plimouth Plantation
Photo: @Reizigerin / Flickr

Whatever you do, don’t miss the living museum of Plimouth Plantation, arguably the highlight of all Plymouth’s attractions. Stepping inside, it truly feels as if you’re in the early 1600s, with fragrant kitchen gardens, heritage livestock and barns, and modest timber-framed houses furnished with reproduction household items like those the Pilgrims would have own owned. This site alone is one of the best day trips from Boston, even if you skip the rest of Plymouth.

Re-creations are based on the many first- and second-hand accounts, records, articles, and artifacts. In the 1624 English Village section, interpreters are trained to dress, act, and speak appropriately for the period, passionately telling their tales about life during America’s early years.

Distance from Boston: 40 miles (approx. 50 mins)

4. Martha’s Vineyard, Massachusetts

day trips from boston
Photo: Aubrey Odom

Located near Cape Cod’s south coast, you’ll reach Martha’s Vineyard via the Island Queen Ferry, which sails from Falmouth to the town of Oak Bluffs, well known for its colorful gingerbread cottages.

You won’t need to rent a car to explore. Park near the Falmouth Dock on the mainland and hop on the ferry. Once you get to Oak Bluffs, it’s far easier to take advantage of the bus, rent bikes through Martha’s Vineyard Bike Rentals, or enjoy the attractions within walking distance (like Oak Bluffs Town Beach) than it is to bother driving around.

flying horses carousel
Photo: Massachusetts Office Of Travel & Tourism

For an absolutely charming experience (and a fun photo op), head to the Flying Horses Carousel – not that you’ll be able too avoid it if you’re traveling with kids, of course. Built in 1876, it’s the country’s oldest operating platform carousel. The hand-painted horses on it have been lovingly preserved and still have their original horse-hair manes and tails. Riders aim to collect as many rings as they can when riding by the metal ring dispensers – the one who catches the brass ring scores a free ride. It’s considered a must-do experience in Oaks Bluffs and is open between April and October.

If you want to stretch you legs, head to Menemsha Hills, a nature reserve just outside the small town of Chillmark. There, you can climb 308-foot-high Prospect Hill for a breathtaking view that stretches from the island’s rugged shoreline to the Elizabeth and Normal Islands. On the way up, you’ll go by lush plant life. It’s a great spot for an easy hike and a picnic.

And if you need a spot to pick up some supplies for that picnic, head to Black Dog’s Water Bakery.  It’s a popular place to stop for lunch or grab some delicious baked treats just before catching the ferry back to Falmouth or heading on a hike. As the name implies, it’s well-known for its fresh baked goods like scones, pastries, cookies, and muffins. It also offers chowder and sandwiches; the Breakfast Woofer Sandwich the hands-down favorite.

Distance from Boston: 90 miles (approx. 2.5 hours)

Related read: 11 Things to Do in Oak Bluffs, Martha’s Vineyard

5. Newport, Rhode Island

day trips from boston
Photo: Steve Geer

Newport is a beautiful seaside city with cobbled streets, a number of idyllic beaches, and a downtown area filled with boutiques, galleries and waterfront restaurants.  It’s one the country’s top sailing destinations, but there’s still plenty to do if you don’t know a mainsail from a jib.

When you’re in need of a bite to eat, pop in for a lobster roll at Brick Alley Pub & Restaurant. Their lobster rolls were voted the best in the country by Bon Appetit magazine.

Newport Rhode Island Mansions
Photo: iStock

Newport may best be known for its grand mansions, with 11 of them open to the public for touring. The Breakers, a National Historic Landmark operated by the Preservation Society of Newport County, is the most magnificent of them all (and certainly the most famous.)

Owned by the Vanderbilt family, it was built as a summer cottage in 1893, though part of its purpose was to make sure everyone in the area knew how wealthy and powerful the family was – it’s certainly not a modest home. The Italian Renaissance-style palazzo has 70 rooms spread across over 65,000 square feet, plus a vast, perfectly manicured lawn with amazing ocean views.

Cliff Walk Newport Rhode Island
Photo: iStock

When you’re ready to spend some time seaside, head to the approximately 3.5-mile-long Cliff Walk. It’s the city’s most popular place for a stroll, stretching along the shoreline with views of the breaking waves and luxurious mansions.

If you want to get in the water, head to First Beach (also known as Easton’s Beach) with gorgeous view of the Cliff Walk plus attractions for the kids like an aquarium, carousel, and big playground. If you want to combine your beaches with some history, aim for Fort Adams State Beach in Fort Adams State Park. Newport is one of the best day trips from Boston, but it’s also a great place to spend the night as there are plenty of charming seaside B&Bs in the area.

Distance from Boston: 72 miles (approx. 90 mins)

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