14 Fun Day Trips from Boston

14 Fun Day Trips from Boston When you need a change of scenery, New England is accessible enough venture out to explore new territory and return home in time to sleep in the comfort of your own home.

14 Fun Day Trips from Boston Any of the seasons present a fantastic time to explore places just quick drive away.  Summer offers access to many beaches, lakes & mountain retreats, while fall features the splendor of foliage trips, apple picking and harvest festivals; and winter is prime for skiing near Boston and snowboarding resorts, 

While there are plenty of activities to experience in the Boston area, day trips can often be a very enjoyable diversion. 

New England offers everything from small quaint historic towns, camping and the great outdoors, to unique museums, amusement parks, ski resorts, amazing beaches,  and more. Check out our hearty list of our favorite day trips within a hop skip and a jump from historic Boston.

14 Fun Day Trips from Boston Day Trips West of Boston

Old Sturbridge Village, Sturbridge MA

Revisit the 1830s at Old Sturbridge Village’s living history museum. The Sturbridge Village museum re-creates the daily work activities of a rural 19th-century town in authentic, living history. Spend the day exploring an entire town including homes, a blacksmith shop, working farm, and more.  Take a horse drawn carriage ride, dip candles, and immerse yourself in history on this easy day trip.

Eric Carle Museum of Picture Book Art, Amherst MA

Wander through the open air hallways of the Eric Carle Museum of Picture Book Art which features rotating exhibits of over 1200 pictures by the children’s book author and artist and others.   Enjoy hands on exploration with the interactive displays of Paddington Bear, Eric Carle and several other children’s authors. Catch some cartoons in the auditorium and create some of your own art in the art gallery.

Purgatory Chasm, Sutton, MA

This unique natural landmark, Purgatory Chasm is different than any other state park around. Instead of just walking through the woods, it’s about climbing rocks big and small.  The chasm trail runs for a quarter of a mile between granite walls rising as
igh as 70 feet. Trails lead to a wide variety of rock formations, with offbeat names as The Corn Crib, The Coffin, The Pulpit, Lovers’ Leap and Fat Man’s Misery.

Day Trips North of Boston

Rockport, MA

In addition to a quaint walking center, amazing views, a small beach, art galleries, shopping and a long rocky pier, Rockport offers an enjoyable afternoon in a true New England Town.    We like to start out visit off with a view of Motif #1 – the famous Red shack that sits in the inner harbor area of Rockport. It’s considered to be one of the most painted venues in the world.

Next, you can take in some shopping in Bear’s Neck and up and down Main Street.   Eclectic stores carry all sorts of wonderful merchandise, apparel, knick knacks, as well as high end art.   Be sure to walk to the end of Bear’s Neck for a walk out onto the rock pier. This is a great place to catch a breeze, and watch the boats come in and out of the Harbor.

The General store is a fun stop for some nostalgia; to get some old-time penny candy, listen to the player piano , and just peruse all the cool stuff they have.  Plus on hot days – this is a cool place to duck into to get out of the heat.

We definitely recommend grabbing a table at Roy Moore’s for some freshly steamed lobster, and shucked oysters.  This place is an institution here in Rockport, and a visit here wouldn’t be complete without a stop here. Afterward, stop in at Robin’s Nest for some delicious, freshly made gelato.

North Shore Beaches

During the summer, head up to the North Shore area for a splendid day at the beach.  Both Good Harbor (fun waves, boogie boarding and fun at low tide); and Wingaersheek Beach  (no waves, great tidepools at low tide, and a long sandbar), are both excellent choices in Gloucester.   

We are also big fans of Crane Beach in Ipswich, which features miles and miles of pristine beach, a large parking lot and is run by the Trustees of Reservations.  Salisbury Beach State Reservation is another great option and, (aside from Crane) the one that includes the most ample parking.

Salem, MA

Travel 16 miles North of Boston to Salem, MA, and step back in time to the era of the Salem witch trials.  Visit the Salem Witch Museum and learn about the trials, where 20 innocent people were put to death in 1692. See the U.S. Custom House and the House of the Seven Gables. is an excursion rich in American heritage and international culture.  While in Salem, take a sail on the Schooner Fame of Salem, an authentic replica of the successful privateer from the War of 1812. 

York, Maine

Also just a short ride up the coast and less than two hours from Boston, York offers lots of options for families with kids to enjoy. Visit York’s Wild Animal Kingdom for a day at the zoo, or the amusement park (or both!). It’s fun to stroll down main street to grab a bite to eat or hit one of the candy stores as you make your way to the beach! The beach has invigorating water, decent waves, as well as a small arcade and a playground to enjoy.

Portsmouth, NH

Explore the gardens and see live entertainment in Prescott Park, whoosh and splash at Water Country, or spend the day on a historic adventure in Portsmouth, a seacoast town that is closer than you’d expect – just on the other side of the New Hampshire border.

Day Trips South of Boston 

Mayflower II

Another great history attraction includes Plimoth Plantation and Mayflower II, a full-scale replica of the 17th century Mayflower, which famously brought the Pilgrims from England to Plymouth Rock in 1620. 

Visitors can take a tour of the ship and learn all about its historic voyage, as well as to board the ship, and interact with costumed 17th-century role-playing reenactors. 

Mayflower II just received a full restoration ahead of Plymouth’s 400th commemoration of the Pilgrims’ arrival on New England’s shores.  

Plimoth Plantation includes a number of historic outdoor living exhibits, including the 17th-Century English Village, Wampanoag Homesite, and the Plimoth Grist Mill.  At the Craft Center, visitors are invited to learn more about how these skilled craftspeople recreate the world of the 17th century.

Fun Day Trips from Boston South Shore Beaches

Across the street from Nantasket Beach in Hull, save time for a ride Paragon Carousel and visit the Paragon Park Museum to relive the amusement park’s glory days as a playground for the rich and famous. A visit to Farfar’s Danish Ice Cream or Scoops is always fun after a day at Duxbury Beach.  

Fun Day Trips from Boston Provincetown, MA

Located at the northernmost hooked tip of Cape Cod Provincetown, affectionately called P-Town has been the long-standing hangout for artists, musicians and the LGBTQ+ community.

Home to dozens of art galleries, great restaurants and shops, Provincetown is has a bit of an edgy vibe with a more traditional backdrop of Cape Cod.  It’s fun to walk around the town, and along the piers. There are often Tall Ships for visitors to see, along with great views of Cape Cod Bay.  

For the best view, visit the Pilgrim Monument and Museum.  The tower is 252 feet, 7.5 inches (77 meters) tall and rises 350 feet above sea level!  The heart-healthy climb to the top on 116 steps and 60 ramps only takes about 10 minutes at a leisurely pace.  You’ll be rewarded with some amazing views. 

The monument commemorates the Mayflower Pilgrims’ first landing in the New World in Provincetown, in November 1620.  The Pilgrims actually spent 5 weeks exploring the tip of Cape Cod, before they sailed on to Plymouth.  

The easiest way to make this a day trip from Boston is to take the Fast Ferry from Boston, or Fast Ferry from Plymouth.  Each trip takes about 90 minutes each way and generally departs at 9:00am with a number of return times.  Check with the concierge on board for ideas on fun things to do when you arrive.  

Fun Day Trips from Boston Newport Mansions, Rhode Island

Take a trip to the most elite and expansive historic mansions with a visit to the Newport Mansions. View two centuries of American architecture, history and decorative arts in the grand villas of the powerful men and influential women who made Newport America’s leading resort and a center of the arts and architecture.

Take in an audio tour and bolster your tours with lots of interesting stories and details that you would otherwise miss.  Meander through the vast and beautiful gardens and stop in the gifts shops for some unique souvenirs.

Fun Day Trips from Boston Providence, RI

Visit the Providence Children’s Museum, or the Roger Williams Zoo & Park.  This large zoo features giraffes, elephants, otters, zebras and more glorious creatures,  Make a day of it and enjoy the award-winning Roger Williams Park, which attracts more than 2 million visitors per year.  Meander through the animal habitats and enjoy a picnic lunch and some frisbee in the shady park just outside the zoo.

Waterfire Providence

For a fun and memorable evening activity, try to time your visit with the Waterfire Providence schedule.  On select nights from May through November, downtown Providence is set ablaze in the most artistic of ways.  WaterFire – a fire sculpture by Barnaby Evans – centers on a series of 100 bonfires that blaze just above the surface of the three rivers that pass through the middle of downtown.

The string of fires illuminates nearly two-thirds of a mile of urban public spaces and parks, and residents and visitors gather to stroll along the river while listening to a memorable and eclectic selection of classical and world music.

Boston is just a car ride away from many wonderful destination, plus it’s an amazing city on its own.  Find lots more things to do in Boston, in our guide to must-see venues within the city as well.