Best Weekend Getaways in Massachusetts Guide

Living in New England means there are almost too many options for weekend getaways! Whether you’re driving down from New Hampshire or Maine or coming up from Connecticut or Rhode Island, where do you begin with your options for unique getaways in Massachusetts? It depends on what you’re looking for — ocean views, American history, or outdoor music — because Massachusetts has them all. After reading this list, you’ll know the best Massachusetts getaways.

• Best for American history - Boston
• Best for literary, witch trials, and maritime history - Salem
• Best for seafood and beaches - Gloucester
• Best for classic Cape Cod vacation - Chatham

• Best for New England small town charm - Rockport
• Best for romantic weekend - Lenox
• Best for American history - Plymouth
• Best for inclusive vacation - Provincetown

• Best for beach getaway - Martha’s Vineyard
• Best for quick Massachusetts getaway - Concord
• Best for animal and beach lovers - Nantucket
• Best for romantic weekend near the beach - Marblehead

Let’s start with some of the most popular cities in Massachusetts. These cities feature American history, witch trials, literary greats, and more.

• ‌Perfect For:‌ American history
• ‌Best Time to Visit:‌ Late summer or early fall
• ‌If You Go:‌ Try not to bring a car, as parking is hard to find and expensive. If you’re driving in from another state, like Vermont, consider booking airport parking and leaving your car there while you’re in the city. It’s likely to be your cheapest option.

From Vermont, drive down 1-89S to 1-93S. From New Hampshire, 1-93S. Or, it’s a little over a one-hour flight from New York City.

One of the best weekend getaways to Massachusetts is a couple of days in the Hub. Walk the freedom trail and learn about American History from costumed guides. Wander through the Commons or Public Garden and stop to ice skate on the Frog Pond in the winter, or ride on a Swan Boat for spring and summer romance. Book a reservation at an Italian restaurant in the North End and enjoy authentic pasta in brick-walled, historic ambiance. This East Coast gem always delights visitors.

• ‌Perfect For:‌ Literary, witch trials, and maritime history
• ‌Best Time to Visit:‌ Late spring or early fall (before October!)
• ‌If You Go:‌ It’s easy to get around on foot if you take the train into the city.

If you’re traveling out to Salem from Boston, take the commuter rail from North Station. If you’re coming from the North, take 1-83S, 1-93S, or 1-95S.

Take it from someone who lived on Essex Street for two years — unless you enjoy obnoxious college kids jumping out at you from behind bushes, avoid Salem during October. The best time to visit is late spring when the flowers are blooming or early fall when the leaves start changing. Enjoy wandering down the cobblestone Essex Street and admiring historic buildings. It’s in the heart of the city and home to the Peabody Essex Museum, where you can learn about the city’s maritime history. Book a tour to learn about the witch trials and ghosts of Salem’s past for a fun, kitschy day.

From Essex Street, continue down to the waterfront. Many of Salem’s attractions are within walking distance. Literary lovers will enjoy tours of the House of the Seven Gables and mariners can grab an ice cream and wander around the marina admiring the boats. If you can’t spend a weekend, it’s a great city for a day trip or a quick Massachusetts getaway.

• ‌Perfect For:‌ Seafood and beaches
• ‌Best Time to Visit:‌ Summer
• ‌If You Go:‌ beach parking fills up fast, and spots for non-residents are reserved. Reserve a spot early online to make sure you get parking.

From Boston, take the commuter rail out of North Station. Drive down on 1-95S from Maine, 1-89S from Vermont, or up from 1-84E to 1-90E.

Made famous by the movie The Perfect Storm, Gloucester still has a strong fishing community. Visit the Cape Ann Museum to learn about the industry’s impact on the town. Then spend a relaxing afternoon lounging one of its beaches such as Niles Beach or Good Harbor Beach. It should come as no surprise that Gloucester has amazing seafood restaurants, such as the Blue Collar Lobster and Cafe at the Gloucester House Inn where you’ll sit right outside on the water, to top off your day.

• ‌Perfect For:‌ A classic Cape Cod vacation
• ‌Best Time to Visit:‌ Summer
• ‌If You Go:‌ Book any stay early in the season to save money and ensure you get a room

From the North, drive down MA3-S to US-6E. It’s also a quick flight on Cape Air.

Chatham is popular with visitors to Cape Cod who enjoy strolling down Main Street with an ice cream cone, taking a tour to look at seals, or visiting the lighthouse. Spend a day at Chatham Lighthouse Beach and see the lighthouse, established in 1808. Kids will delight in watching the seals catch discarded bait from the observation deck at Chatham Fish Pier, or book a boat tour to see the seals in Pleasant Bay.

In true New England fashion, you and the kids can go clam digging at Ridgevale Beach and Chatham Bars Inn Beach, both good spots for quahogs and soft-shell clams. Later that night, cook them over a fire pit. You can do a lot for free in Chatham, and a weekend in Cape Cod is an option for affordable getaways in Massachusetts.

These unique weekend trips are outside of the major cities. They give you small town charm, romance, great eateries, and American history.

• ‌Perfect For:‌ New England small town charm
• ‌Best Time to Visit:‌ Spring and summer
• ‌If You Go:‌ Plan a mix of activities to truly explore the town and its surroundings.

From the West drive 1-93N to MA-128N. From the North head down 1-95S to 1-295S.

New England small towns have their own special charms. A weekend in the coastal town Rockport feels like a stroll through the heart of America. The Rockport Downtown Main Street Historic District has gift shops, antique stores, and adorable boutiques housed in historic buildings.

After exploring the town, visit Halibut Point State Park to admire its stunning views of Maine and the Isles of Shoals off New Hampshire. The hiking and scenic viewing is unparalleled, and the former granite quarries a truly unique site. Take a kayak out on Cape Ann or bike through town, rentals are available if you don’t want to bring your own.

• ‌Perfect For:‌ A romantic weekend
• ‌Best Time to Visit:‌ Late summer to early fall
• ‌If You Go:‌ Take your time enjoying nature; the Berkshires is famous for its fall foliage

From the East drive out on 1-90W. From the North, 1-91S to 1-90W.

This charming town in the Berkshires is a great spot for a romantic weekend. In the fall, you’ll stroll hand-in-hand under a brilliant canopy of gold, red, and orange leaves on the seven miles of hiking trails at the Pleasant Valley Sanctuary. If you visit near the end of summer you can still catch an outdoor music show at Tanglewood, which features both popular acts and the Boston Symphony Orchestra. Sit outside on a blanket and cuddle with your honey while you listen to great music.

For a romantic evening, book a reservation at Bistro Zinc in the heart of town or dine by the Gilded Age fireplace at 1894: A Miraval Experience. As romantic getaways go, it’s sure to send you home with your hearts full.

• ‌Perfect For:‌ American history
• ‌Best Time to Visit:‌ Late spring or early fall
• ‌If You Go:‌ there’s not much parking around the downtown area, but there are local, paid lots near the waterfront.

From the North drive down 1-93S to MA3-S or take the commuter rail from South Station.

While some say that Plymouth Rock isn’t too impressive, it’s still an important site in American history. Lit up at night, with the ocean in the background, it’s quite beautiful. The waterfront and downtown area is chock full of historic sites, and you’ll see the names of the nation’s founders on many buildings.

During the late spring to early fall join costumed guides at Plimoth to learn about Pilgrim life and explore a 17th-century village. While complicated, learning about our nation’s history can make for a fascinating weekend.

• ‌Perfect For:‌ An inclusive vacation
• ‌Best Time to Visit:‌ Early or late summer
• ‌If You Go:‌ Take the time to check out art galleries.

Two ferry lines go from Boston to Provincetown. From the seaport, hop on a Bay State Cruise Company high-speed ferry, or take the Boston City Cruises boat down.

Provincetown, or P-Town, is known for its inclusive and welcoming vibe. As home to the oldest continuous arts community in America it’s become a safe place for all families to visit. Walk down the main street, Commercial Street, and in and out of bakeries and art galleries.

Spend some time on the water or at the beach while you’re in P-town. There are several options to book a whale watching excursion and head out on the ocean to admire the magnificent creatures. There are also kayak and paddleboard rentals available if you’re bold enough to go kayaking in the bay.

P-town is one of the best Massachusetts getaways for people who want the freedom to be themselves.

It’s not hard to find a spot for one of the best weekend getaways in Massachusetts. We have American history, beaches, great restaurants, and more. But sometimes you just need a few more options to plan interesting and affordable getaways in Massachusetts.

• ‌Perfect For:‌ A beach getaway
• ‌Best Time to Visit:‌ Summer
• ‌If You Go:‌ Check parking restrictions at the beaches or book a hotel within walking distance. They get crowded in the summer.

If you’re headed up to Massachusetts from a more Southern state like New York you probably won’t want to head out to the North Shore if you’re looking for beaches. Martha’s Vineyard is a 5-hour drive from New York up 1-95N to 1-195E, or you can hop on a short flight.

Beaches, biking, and lighthouses, you’ll find the perfect summer escape on Martha’s Vineyard. Five lighthouses look out over Vineyard Sound and Nantucket Sound, though Gayhead Light is the only one that offers tours. Visit these picturesque spots while biking around the island — there’s a great four-mile loop from the West Chop lighthouse to Vineyard Haven.

If you flew up to spend a day at the beach, you’ll find the most options in Edgartown — if you stay in town you can walk or bike down to Fuller Street Beach. It’s hard to find parking at some of the other beaches, or the town’s limit parking to residents.

The island of Martha’s Vineyard preserves its New England charm by limiting chain hotels (there’s only one on the island) and restaurants. The island abounds with boutique hotels like the Hob Knob Luxury Boutique Hotel and Spa. Enjoy beautifully appointed rooms in the classic Gothic Revival style inn and book a massage to end your weekend on a high note before heading back to the hustle and grind.

• ‌Perfect For:‌ A quick Massachusetts getaway
• ‌Best Time to Visit:‌ Early to late fall
• ‌If You Go:‌ Pack a lunch and snacks to save money

From Boston it’s a short drive on 1-90W to 1-95N.

Fall leaves and literary loves — Concord has an unmistakable appeal. Fans of Louisa May Alcott visit the town to tour Louisa May Alcott’s Orchard House, the home of Little Women, which is open year-round. If you prefer poetry, hike around Walden Pond, memorialized by the works of Henry David Thoreau. It’s at its best in the fall when trees burst forth with glorious color.

This is among the most affordable getaways in Massachusetts because a visit to Concord can cost you as little as the price of gas and an admission ticket. Pack a picnic lunch to enjoy outside on the grounds at Orchard House or the beach at Walden Pond.

• ‌Perfect For:‌ Animal and beach lovers
• ‌Best Time to Visit:‌ Late spring, early summer, and late summer
• ‌If You Go:‌ Book a reservation in advance for the ferry if you plan on bringing your car. Spots fill up fast.

Drive down to Hyannis and take the ferry over to the island.

At night, sit out on the beach around a fire pit and gaze up at the stars. During the day, rent bikes and explore. There are three main bike trails, of varying difficulties and length, that connect Surfside, Siasconset, and Madaket.

Animal lovers should visit the national park at Nantucket National Wildlife Refuge, home to a diverse number of wildlife species. See grey and harbor seals in their natural habitat, try to spot piper plovers and American oystercatchers in the wild, and look up into the sky for a glimpse of raptors.

• ‌Perfect For:‌ A romantic weekend near the beach
• ‌Best Time to Visit:‌ Summer for boating events and festivals.
• ‌If You Go:‌ Boating and yachts are popular here.

From Boston take 1-93N to 1-95N. From points north you’ll take 1-95S.

Located on a rocky peninsula that stretches into the Atlantic Ocean, Marblehead is a romantic spot. Head out on foot for a historic walking tour, drop into unique boutiques, visit Chandler Hovey Park and the Marblehead Lighthouse. Then, book a reservation at the Caffe Italia Trattoria with dim lighting and exposed brick, or gaze out at the harbor at The Landing Restaurant.

If you plan on staying overnight, book a room at bed and breakfast Harbor Light Inn. After filling up on a full breakfast, including fresh breads made on-site, you can head out to the nearby harbor, historic homes, and shops. Six of their rooms have fireplaces for a romantic evening.

The best weekend getaways in Massachusetts are only a short drive, train, or flight away. The state offers history, nature, and and a welcoming spirit.