Weekend getaways and day trips from Massachusetts [within driving distance]

Published May 19, 2024

If you’re looking to save on airfare, or have limited time off from work, weekend getaways and day trips can fulfill the urge to get away without taking too much out of your busy weeks (or your wallet). When you live in Massachusetts, there are plenty of places to explore that are within driving distance. At Webster First, our mission is to help our members save money. So pack up those cars and get ready to experience the place you call home in ways you may never have before.


Best cities within driving distance


Boston, MA

Our great capital of Boston has loads of fun things to do. With a city so rich in history, there are several options for guided tours. Take your pick of the many history, art, or science museums Boston has to offer. You can dine with harbor views in the Seaport District, or catch a performance in the Theater District. Shop at Downtown Crossing and stop and smell the flowers at the Boston Public Gardens. Foodies should definitely check out Quincy Market in Faneuil Hall – which also has a vibrant nightlife scene.

The best thing about visiting Boston is that it’s very easy to get around the city either by walking or a quick trip on the T. Driving on the other hand…not ideal. If you have the money to spend on an expensive parking garage and you don’t mind driving in congested traffic, go ahead and bring your car. But if you’d like to avoid that, the commuter rail might be for you.

Boston skyline on a clear day over Charles River with boats on the water

Photo by Angela Talbot

Salem, MA

Salem is only a 30-40 minute drive north of Boston. It’s located on the coast and, as we’re sure you know, also has rich witch history. There are museums surrounding the history of the witch trials open year-round, and the Peabody-Essex Museum is worth visiting for art lovers. If you’re a fan of the movie Hocus Pocus, you can see where they filmed the exterior shots of Max and Alison’s houses. In the months of September and October, it gets EXTRA witchy in Salem, attracting tourists from all over the world. Haunted houses open, a carnival is set up on the town common, and a very large vendor fair takes over Essex Street.

TIP! If you’re only interested in visiting the year-round attractions, we’d recommend going in the spring or summer to avoid these large crowds. During the fall, you may be able to find parking in the visitor center or along certain streets if you get there very early in the morning. Most streets, however, are marked “Residential Parking Only.” We recommend finding other transportation or booking accommodations that have parking available.

Bewitched Statue in Salem, Massachusetts

Bewitched Statue. Photo by Caroline Moore

Springfield, MA

What can you do in Springfield for a day? Well, you could see the Naismith Basketball Hall of Fame, as the sport was invented right here! Or, you could visit the Amazing World of Dr. Seuss Museum and stop by the Dr. Seuss National Memorial Sculpture that’s part of the Springfield Museums – one stop for five museums – history, art, fine arts, science, and Dr. Seuss.

Animal lovers will enjoy the zoo inside Forest Park. Oh, and if you drive to the neighboring town of Agawam, you can go to Six Flags New England. Ok…maybe it will take you more than one day to do all these things. Plus, visit during the month’s of September or October and you could attend the biggest fall festival in Massachusetts, the Big E!


Providence, RI

Providence is a small city with a big culture. You can visit the Museum of Natural History & Planetarium on Elmwood Ave. The Rhode Island School of Design has its own art museum that is open to the public. The Providence Performing Arts Center hosts plays and concerts throughout the whole year.

During most nights in the summer, Waterplace Park comes alive with the “WaterFire” art installation. Fires which appear to be floating on the water of the Woonasquatucket River are lit in a display that draws business to the restaurants, bars, and retail stores nearby. Don’t miss the opportunity to stop at Roger Williams Park and see the zoo – one of the best in New England!


Portland, ME

Portland is a peninsula along the coast of Maine extending into Casco Bay. Visit the famous Portland Head Light – a lighthouse located in Fort Williams Park where it is impossible to take a bad photo. The Old Port district is a neighborhood with cobblestone streets, shopping, nightlife, and can’t-miss waterfront dining experiences of fresh seafood. Maine is known for its lobster so definitely try some!

The Casco Bay islands are a short ferry ride away, and there you can take guided kayak tours of the bay, bike, fish, or golf 9-holes on Chebeague Island’s Great Chebeague Golf Club. You can even find sea glass on the beaches of these islands, especially Peaks Island.

Portland Head Light, Maine Lighthouse

Portland Head Light, ME. Photo by Angela Talbot


Burlington, VT

Burlington is a bustling city along the coast of Lake Champlain and home to the University of Vermont. Check out ECHO, Leahy Center for Lake Champlain, a science museum exploring the ecosystems of the lake. Or see the Fleming Museum of Art. The Flynn is the local venue to catch live music, and if you like beer, there are a handful of breweries in the area. Burlington was also the home to Revolutionary War hero Ethan Allen, and his Homestead has been turned into a museum. Vermont is known for its maple syrup, so look for a spot to taste some locally made!



Best coastal towns within driving distance


Cape Cod, MA

We know Cape Cod isn’t just one town…but any place you decide to visit on the Cape is going to be a nice trip. Whether you stop in Hyannis or drive all the way to Provincetown, you’ll find beautiful beaches, great seafood, and lots of fun for the family. Adventures on the Cape include golf, mini golf, go carts, water parks, craft shows, ice cream shops, and souvenir shops.

Whale watching tours are a popular tourist attraction out of Provincetown. Adventure Park at Heritage Museums and Gardens in Sandwich is an “aerial forest park” for all ages. The kids will also love The Cape Cod Inflatable Park in West Yarmouth. This list goes on and on. Visit capcodchamber.org to find more things to do.

Whale tail emerging from ocean water in Cape Cod Bay. Provincetown whale watch

Provincetown whale watch. Photo by Caroline Moore

Martha’s Vineyard, MA

Martha’s Vineyard is an island off the coast of Cape Cod which you can only get to by ferry or plane. Tourists travel to Martha’s Vineyard for shopping, sandy beaches, lighthouses, and seafood.


York, ME

There are way too many beautiful beach towns in Maine to just pick one. But, we’re naming York because it is one of the closest to Massachusetts. York is near many golf courses, is a short drive from Mount Agamenticus, has its own zoo (York’s Wild Kingdom), and is close enough to several of Maine’s other most popular beaches like Ogunquit, Old Orchard, and Wells.

Palace Playland Ferris Wheel at Old Orchard Beach, Maine

Old Orchard Beach, ME. Photo by Angela Talbot

Hampton, NH

Hampton Beach in New Hampshire is a popular summer destination known for its boardwalk where you can find arcades, souvenir shops, restaurants, and ice cream parlors. Stay at a hotel, motel, or campground. Catch a music or comedy performance at the Hampton Beach Casino Ballroom or get to know the sea creatures at the Explore the Ocean World Oceanarium. There’s a lot to do at Hampton Beach.


Block Island, RI

Travel to Block Island by ferry from Point Judith, RI, Newport, RI, or New London, CT. The island is known for its popular beaches, historic lighthouses (which you can tour), retail shops, and art galleries. Hikers can enjoy scenic trails leading to cliffside ocean views.  Watersports like parasailing and jet skiing are also popular activities on the island.

Block Island Beach

Photo by Caroline Moore

Bar Harbor, ME

Bar Harbor is where you can find Acadia National Park – known for its cliffs overlooking the Atlantic Ocean and a vibrant display of foliage in the fall. It’s a great vacation spot for hiking, cycling, kayaking, rock climbing, and camping. And, as with any other town in Maine, great lobstah!

Maine Lobster Roll

Maine Lobster Roll. Photo by Angela Talbot


Best mountain towns within driving distance


Stockbridge, MA

Stockbridge is located in the Berkshire mountains near the border of New York. In addition to mountain hiking and biking, you can visit the Berkshire Botanical Gardens or one of several mansions and estates in town. Famous painter and writer Norman Rockwell used different locations around Stockbridge as the subjects of several of his paintings. Because of this, Stockbridge is home to the Norman Rockwell Museum, which showcases a significant collection of his original works.


Conway, NH

Conway, New Hampshire has one of the most famous highways in the world which passes through the White Mountains: Kancamagus Highway. Its winding roads leave nothing but trees for miles, making it a popular destination for foliage viewing in autumn. Conway is home to many ski resorts, the Story Land amusement park, and the famous Mount Washington. You can drive your car to the top of Mount Washington when the weather is warm.

White Mountains, North Conway, NH in winter. Snow covered ground and river.

White Mountains. Photo by Angela Talbot

Stowe, VT – Lincoln, VT – Killington, VT

Okay, so there are a lot of good mountain towns in Vermont – take your pick. Each of these towns has mountains that provide incredible views at the top. On a clear day, you can even see Mt. Washington from many of the peaks. So, whether you like hiking, camping, or skiing, these towns are the place to be.  When you’re not on the mountains, you may find yourself sightseeing some of Vermont’s famous covered bridges, eating some Ben & Jerry’s ice cream, or visiting a farmers’ market.


Convenience in any state

Wherever you’re traveling, you can get cash from your Webster First account with no surcharge fees at one of the nearly 30,000 ATMs in our SUM and CO-OP networks. With shared branching, you can find a credit union to make deposits in-branch too! Visit our Branches & ATMs page to find one near you.

Make sure you’re protected

It’s important to have car insurance you can rely on when you’re traveling long distances. Our subsidiary WebFirst Insurance, LLC can get you the coverage you need so you don’t have to worry if your road trip hits a speed bump.

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Disclaimer: Webster First was not paid to endorse or evaluate the businesses, services, or companies mentioned in this post.