25 Best Day Trips & Small Towns in Massachusetts

By VacationIdea Staff on October 2, 2022 - Updated

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Day trips from Massachusetts include several quaint historical towns with structures and history dating back to the early 17th century when European settlers first arrived on the state’s eastern shore. From the seaside fishing and whaling towns north and south of Boston, to the picturesque beaches of Cape Cod, to the bustling cities of Boston and New York, there’s something for everyone to see and do.

We recommend that you call the attractions and restaurants ahead of your visit to confirm current opening times.

1.Acushnet

Acushnet was founded in 1860, as separate from the greater Fairhaven area. It’s the site of the oldest ceremony and church building in the area, each dating back to the 1700’s. The 23-acre cemetery is the burial place of some of Massachusetts’ earliest settlers, including soldiers who fought in the Revolutionary War. Other attractions in the area include the Long Plain Museum, which occupies an 1875 schoolhouse, and educates visitors on local history. The 1799 ruins of a water-powered cotton mill still stand along the Acushnet River. The New Bedford Reservoir, known as Lake Street to the locals, offers kayaking, fishing and wildlife observation.

Acushnet, MA 02743

2.Boston

Boston is among the most visited New England towns and offers a rich history, diverse culture, and great respect for the arts and education. Self-guided walking tours and trails throughout the city include the Freedom Trail, which passes by 16 historical sites, the Irish Heritage Trail, Black Heritage Trail, and Women’s Heritage Trail. Climb to the top of the Bunker Hill monument, which celebrates America’s first major win of the American Revolution, visit the Boston Common and the Public Gardens, the city’s central public parks, which together form part of the 1,100 acre Emerald Necklace. World-renowned museums include the Museum of Fine Arts, Museum of Science, Children’s Museum and the New England Aquarium.

Boston, MA 02116

3.Cambridge

Home of Harvard University, Cambridge sits across the Charles River from Boston proper and offers historical sites, excellent dining and shopping, and outdoor activity. Dive into history at the Cambridge Historical Society, located in the 1685 Hooper-Lee-Nichols House. Stroll through the Cambridge Common public park, or visit the historic Cambridge Public Library. Take a riverboat tour past Harvard’s famous boathouses along the Charles River. Stroll through Harvard Square for the best of the area’s shopping and dining. Within the Harvard campus, visit the famous glass flowers at the Botanical Museum, tour the Museum of Natural History for an exhibit of over 200 bird families and to browse the collection of more than 150,000 insects.

Cambridge, MA 02138

4.Cape Cod

Cape Cod is the arms of Massachusetts that extends into the Atlantic Ocean. The cape offers a range of small town experiences, beach going and outdoor recreation on the north and south shores. Head to the northernmost tip of the arm for a visit to the Cape Cod National Seashore, described by Thoreau in the 1800’s as the great outer beach. The National Park protects over 43,000 acres of historic lighthouses, cranberry bogs, seashore and wildlife. Enjoy seafood via casual or fine dining in any of the 15 Cape Cod towns. Try classic New England clam chowder, a lobster roll, or fried clams.

Cape Cod, MA

5.Castle Hill

Castle Hill is a grand seaside estate in Ipswich. Once known as Agawam to the Native Americans, the area was farmed by settlers as early as the 1600’s, over hundreds of years it transformed from a working farm to a gentleman’s estate, culminating with the 1910 purchase by Robert Crane. Today, the site is occupied by a 59-room mansion built in 1928 in the Stuart-style, also known as restoration architecture for it’s draw from earlier periods. Enjoy a stroll along the grounds of the Crane Wildlife Preserve and the formally landscaped gardens, or tour the first floor of the main house, decorated with period furnishings. Tours include a trip back to 1929, a look at the home from a servant’s perspective, golf-cart tours of the grounds, and a tour to the cupola on the estate’s roof.

290 Argilla Rd, Ipswich, MA 01938, Phone: 978-356-4351

6.Day trips near me: Castle Island Park

Boston’s Castle Island Park offers a combination of outdoor recreation and history. No longer a true island, Castle Island has been connected to the mainland since 1928. Visit Fort Independence, constructed in 1833 to replace the original fort from the 1600’s. The fort feel out of use after the Civil War and is now listed on the National Register of Historic Places. Additional activities at the park include swimming at any of the area’s beaches, walking or running along the Pleasure Bay Loop or fishing. There are restroom facilities with showers, playgrounds and picnic areas with grilling stations.

2010 Day Blvd., Boston, MA 02127, Phone: 617-727-5290

7.Glendale Falls

The Glendale Falls are among the tallest waterfalls in Massachusetts, found where the smaller Glendale Brook tumbles into the Westfield River. A moderate to strenuous quarter mile hike leads from the trailhead to the base of the falls. Surrounding forests are canopied by beech, birch and hemlock trees with maple, mountain laurel and witch hazel beneath. Cross Clark Wright Road to follow a slightly longer trail through a natural wet meadow that parallels Glendale Brook. While open year round, the spring is the best time to visit the falls. Westfield River is a federally designated Wild and Scenic River, which preserves its free-flowing condition to protect wildlife.

Clark Wright Rd, Middlefield, MA 01243, Phone: 413-213-4751

8.Good Harbor Beach

Gloucester, Massachusetts is well known for its seven public beaches, among which is Good Harbor Beach. Good Harbor Beach offers a pleasant stretch of white sand, surrounding dunes and marshes and is best known for its protected swimming conditions. During low tide, visitors can walk to the nearby Salt Island. During high tide, beach goers may enjoy swimming and soft-top boogie boarding. Lifeguards are on duty from Memorial Day weekend through Labor Day. Arrive early in the day for a parking spot, especially during the summer months. While restroom facilities are available, be prepared to pack out all trash with you.

99 Thatcher Rd, Gloucester, MA 01930, Phone: 978-281-9785

9.Hudson

Hudson is a progressive small town in Massachusetts which has embraced the “local first” theme. The support of local small business has encouraged a weekly town farmer’s market, local breweries and speakeasy’s, local ice cream shops and award-winning farm-to-table dining. A historic mill town that was once a manufacturing hub, the area has revitalized through its commitment to the support of local agriculture. Visit the famous Mullahy’s Cheese for local cheeses, honeys, figs, and baked goods. The tap room at Medusa Brewing Company offers up to 100 lagers and ales, including lunch and dinner. Shop the quaint boutiques along Main Street, and of course, visit one of the many farmer’s markets.

Hudson, MA 01749

10.Ipswich

Ipswich is a small town on the coast north of Boston with great beaches, dining and fun things to do for a summer visit. Visit Appleton Farms, among the oldest operating farms in America, for a walk along their trails, or to purchase cheeses and milk from the dairy cows, baked goods and fresh flowers. At Russell Orchards open since 1920, stop by the farm store for apple-everything, including donuts, cider and pies. Try the traditional fried clams at the Clam Box, a classic 1930’s New England clam shack. Quaint streets are lined with early American houses. Self-guided audio tours of the historic city center are available at the Visitors Center, located in an 1820’s home.

Ipswich, MA 01938

11.Marblehead

Marblehead is a seaside town north of Boston offering history and picturesque views of the harbor or Atlantic Ocean. Once a thriving fishing village in the early 1600’s, the rocky outpost on the Massachusetts coast was among the most populous towns in the colonies prior to the Revolutionary War. By the 19th century it has become an opulent merchant town and seaside resort, known for the sprawling mansions on the cliffs over the sea. Among the main attractions are over 300 colonial-era homes, and a historic district full of boutiques and galleries, restaurants, cafes and bars. Visit the Marblehead Museum, the Marblehead Lighthouse, or the 1638 Old Burial Hill for a unique view of the town.

Marblehead, MA 01945

12.Martha’s Vineyard

Martha’s Vineyard is a small island off the south shore of Massachusetts, accessed by ferry from Cape Cod, New York or Rhode Island. The year-round destination offers pristine beaches, fresh seafood and produce, outdoor activities and events. There are 6 towns throughout the 100-square mile island, each with its own character and charm. Aquinnah is home to the only federally recognized Native American tribe in Massachusetts, the Wampanoag. Chilmark offers nature preserves and rolling pastures. Edgartown is the island’s oldest European settlement, while West Tisbury retains its rural charm. Oak Bluffs and Vineyard Haven are the island’s two bustling ferry port towns. Each offers shopping, dining, boat rentals, fishing charters and more.

Martha’s Vineyard, MA 02539

13.Naismith Memorial Basketball Hall of Fame

The Naismith Memorial Basketball Hall of Fame is a family friendly museum for anyone with a love of basketball. Located in Springfield, the non-profit organization hosts over 40,000 square feet of exhibits related to basketball history, and has inducted over 400 players and coaches into the hall of fame. The original Hall of Fame was founded in 1968 on the Springfield College campus. The current facility was dedicated in 2002, with the hall of fame overlooking an iconic center court. Visitors are welcome to play on the court and under the eye of greats such as Magic Johnson, Mike Krzyzewski and Senda Berenson Abbott. The new facility, along the banks of the Connecticut River, is also home to events, clinics and tournaments.

1000 Hall of Fame Ave, Springfield, Massachusetts 01105, Phone: 877-446-6752

14.Day trips near me: New Bedford

New Bedford is a working fishing port within Buzzard’s Bay on the south shore of Massachusetts. The town offers history, a vibrant artist’s community, local seafood and craft beers. Visit the Whaling Museum for a history of whaling in the area and sailing-dominated merchant days. The New Bedford Art Museum and ArtWorks! are each located within walking distance of several galleries. Historic homes open to the public include the 1834 Rotch-Jones-Duff House and Garden Museum as well as the 1800 Nathan and Polly Johnson home, restored to its 1857 look. Close the day with an evening performance of the New Bedford Ballet or Symphony Orchestra.

New Bedford, MA 02740

15.New York, NY

New York City is easily accessible from Massachusetts via train, bus or car. The year-round destination offers some of the nation’s best museums and art galleries, seven of which are centrally located along the Museum Mile on Fifth Avenue. Enjoy a stroll through Central Park, or alongside the Hudson River. Take in a Broadway show, and shop or dine in Times Square. Top attractions include the observatory atop the Empire State Building, the Museum of Modern Art, the indoor-outdoor complex at Rockefeller Center, and the neo-Gothic St. Paul’s Cathedral. Take a ferry or sailboat to Ellis Island to visit the Statue of Liberty National Monument. Sports fans will enjoy visiting Yankee Stadium or Madison Square Garden.

New York, NY

16.Newport, RI

Newport, Rhode Island is a seaside town just 60 miles south of Boston. Visit for the beaches and take a walk alongside the cliffs between the Atlantic Ocean and the storied mansions of Newport along the 3.5 mile long cliff walk route. For a look inside the mansions, once the summer homes for the world’s most wealthy tycoons, tour the Vanderbilt Marble House or The Breakers. The 10-mile long scenic Ocean Drive offers views of the harbor, dotted by ships, racing sailboats and luxurious yachts. The Museum of Yachting is located at Fort Adams alongside The Eisenhower House for a multi-faceted look at history. The Touro Synagogue, America’s oldest, was visited by George Washington while he was in town promoting the Bill of Rights.

Newport, RI 02840

17.Plimouth Plantation

Plimouth Plantation is a living history museum in Plymouth that offers an example of what life looked like for the early pilgrims who arrived aboard the Mayflower. Outdoor exhibits include a Wampanoag homesite along the banks of the Eel River. Staffed by Native Americans wearing authentic 17th century clothing, the village offers a look at the crafts, cuisine and daily life of Native Americans in the 1600’s. A 17th century English village is staffed by live actors who portray real-life residents of the Plymouth Colony. The Plymouth Grist Mill and a replica of the Mayflower ship herself, the Mayflower II, are located nearby. Plan to spend a full day to enjoy the crafts center, museum gift shop, and rare breed animals at the Nye Barn.

137 Warren Ave, Plymouth, MA 02360, Phone: 508-746-1622

18.Plymouth

Plymouth is a seaside town known for the iconic Plymouth Rock, where pilgrims aboard the Mayflower first reached shore in 1620. Take a history tour aboard a trolley, visit historic homes such as the 1809 Hedge House, the 1797 Cudworth House and Barn, and the Daniel Webster estate. Museums include the 1749 Courthouse, the 1824 Pilgrim Hall Museum, and the Jenny Museum where one can learn about the Underground Railroad movement. The Mayflower Meetinghouse, known as the birthplace of religious freedom in the United States, offers tours and functions today as a the First Parish Unitarian Universalist Church of Plymouth. Beyond history, enjoy the seafood in this coastal town, and shop for locally made arts and crafts.

Plymouth, MA 02360

19.Day trips near me: Provincetown

Provincetown is a progressive, LGBT friendly town on the northernmost tip of Cape Cod. The coastal village known as PTown has been marketed as a tourist destination since the 1800’s when the local fishing industry was greatly impacted by storms. Artists and creatives have long been drawn to the island-like town for its scenic views, the serene bay and fresh air. Provincetown has been a mecca for gay-friendly events and festivals since the 1920’s, and is now a booming artist’s colony. Museums include the Provincetown Art Association and Museum, the Whydah Sea Lab & Learning center and Pilgrim Monument, marking the site early pilgrims first explored before sailing south to Plymouth. Enjoy the beaches, nature and wildlife, shopping and dining.

Provincetown, MA 02657

20.Purgatory Chasm State Reservation

The Purgatory Chasm State Reservation is a protected natural area offering views of several unique geological formations, outdoor recreation and basic facilities with a 100-acre park. Hike a half mile to visit the 70-foot deep chasm between the glacial rocks with names like Devil’s Coffin, Devil’s Corn Crib and Lover’s Leap. While geologists say the fissures were caused 14,000 years ago when a glacier let loose a gush of water, legends abound about Native American gods, devil-like actions and 17th century murder. Outside of the 2-miles of trails, facilities at the park include picnic areas, playgrounds, grilling stations, restrooms and concessions.

198 Purgatory Rd, Sutton, MA 01590, Phone: 508-234-3733

21.Revere Beach

Revere Beach is a hard packed sandy shore in the Massachusetts Bay north of Boston. Ideal for swimming, the crescent-shaped beach offers blue waters protected from waves by the bay. Easily accessed by railroad since the 1800’s, the coastal town has long been an entertainment destination. Rollercoasters, rides and amusements, ballrooms and dance pavilions have lined the shore since the 19th century. Recognized as America’s first public beach, the site is now a National Historic Landmark. Visit the Boston Harbor’s largest surviving salt marsh, the Belle Isle Marsh Reservation, the 1630 Rumney Marsh Burial Ground, and the 1835 Fenno’s Tavern.

Revere Beach, MA 02151

22.Rockport

Rockport is a small coastal town that began as a fishing village and has been a haven for artists for more than 100 years. Visit this historic region of Essex County for cultural experiences, dining and shopping. Enjoy seafood with a view of the bay. At the Roy Moore Lobster Company you’ll find classics such as lobster rolls, fish cakes, stuffed clams and chowder. Walk and shop the historic downtown with its colorful wood-framed buildings. Be sure to visit the Pewter Shop, open since 1935. North Shore Kayaks offers kayak rentals, or simply walk to any of the area beaches to dip your toes in the water.

Rockport, MA 01966

23.Salem

Salem, Massachusetts is famous for the witch trials of the 1690’s in which 19 innocent people were hanged. It is the birthplace of the American writer Nathanial Hawthorne, best known for the Scarlet Letter and The House of the Seven Gables. Take a tour of the 17th century House of the Seven Gables home. Visit the Salem Custom House, a National Historic Site with historic exhibits. At the Peabody Essex Museum exhibits include artwork dating back to the 1700’s, among 1.8 million works from around the globe. Hundreds of walking tours are available for history buffs, foodies, ghost hunters and modern day witches.

Salem, MA 01915

24.Spectacle Island

Spectacle Island is a 105-acre state park within Boston Harbor with swimmable beaches, views of the Boston skyline and hiking trails. Prepare for a day in the sun as very few shade structures exist on the island. Facilities include restrooms, drinking fountains, a snack bar with outdoor seating areas, marina with sailboat moorings and rinsing station. Enjoy hiking around the island and to the top of North Drumlin for scenic views. Bring a picnic, fly a kite, or dip in the water. Events on the island include summertime yoga, jazz performances, ranger guided hikes and sunset clambakes. Ferry service to the islands runs mid-May through mid-October.

Spectacle Island, MA

25.Day trips near me: Webster Lake

Massachusetts’ Webster Lake is the colloquial name for what’s officially called Lake Chargoggagoggmanchauggagoggchaubunagungamaugg. The lake, with the longest name in the United States and the third longest in the world, was named after English colonialists first arrived in the area, and is a Nipmuk Indian name roughly meaning, “neutral fishing and meeting place for white men and Native Americans.” Locals balked at a suggested name change to Lake Chaubunagungamaug in the 1950’s, and the name remains a source of pride for those who can pronounce it. Webster Lake is popular for swimming, fishing and boating. During the winter months, it’s used for ice fishing and snowmobiling.

Webster, MA 01570