Top 35 Amazing Day Trips To Take From Boston, MA

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A trip to Boston doesn’t have to end there. The east coast near Boston is filled with amazing towns and happening spots like Boston Harbor and Harvard Square. With so many historic landmarks and popular destinations at your fingertips, exploring Boston can keep you occupied for weeks, but if you are looking to explore beyond the city, you’ve come to the right place. Luckily, Boston’s strategic location makes it an excellent starting point for numerous day trips to beautiful destinations along the East Coast. 

Whether you’re a nature lover, a history enthusiast, or just seeking a relaxing escape, there’s something for everyone within a short drive from Boston. From small towns and historical sites to the Cape Cod National Seashore and exploring the great outdoors, you’ll have difficulty choosing where to go first. 

In true day trip fashion, these destinations are a two-hour drive or less away from downtown Boston and are all worth visiting, especially during the summer months.

Keep reading for 35 fantastic day trips from Boston!

Woodstock, VT (140 miles, 2 hours)

Nestled in eastern Vermont, the small town of Woodstock boasts picturesque landscapes, charming streets, and historic architecture. You can stroll through this town’s quaint shops, visit the Billings Farm & Museum, and explore the covered bridges that dot the area.

Start with a walk through the village green, grab a coffee from Mon Vert Cafe, and browse through Farmhouse Pottery, an adorable pottery shop. The warmer months offer many outdoor festivals perfect for art lovers, foodies, and supporting local businesses. Don’t forget about Woodstock’s covered bridge trio, including the Taftsville Covered Bridge, the Lincoln Covered Bridge, and the picturesque Middle Bridge. 

Keene, NH (92 miles, 2 hours)

Keene, New Hampshire, located in the Connecticut River Valley, offers a delightful mix of outdoor activities and cultural experiences. If you’re a nature enthusiast, explore the Ashuelot River Park, featuring 157 acres of river, wetlands, hiking trails, and a paved bike path. 

Downtown Keene is another excellent place to enjoy the day – you can spot historic buildings like an old movie theater and the church in Central Square and browse the many antique shops, restaurants, candy shops, and thrift stores. Be sure to check out Hannah Grimes Marketplace. This gift shop has so many unique goods made by local artisans.

Peterborough, NH (73 miles, 1 hour 45 mins)

As you step into Peterborough, you’ll be greeted by several artsy shops, cozy cafes, and vibrant theaters. Don’t miss the MacDowell Colony, an artist’s retreat that has hosted famous writers and composers over the years.

You can also head to Miller State Park for a 3-mile hike to Pack Monadnock, the highest peak in the area. If you’d rather stay inside, explore The Monadnock Center for History & Culture, a museum detailing the history of this region. 

Lincoln, NH (130 miles, 2 hours)

Located in the White Mountains of New Hampshire, Lincoln has an abundance of outdoor activities. Drive along the scenic Kancamagus Highway, a 34.5-mile drive, or embark on breathtaking hikes in Franconia Notch State Park. Lonesome Lake Trail and the Flume Gorge Trail are two local favorites. The Appalachian Trail also crosses this town’s northeastern and western parts, so don’t forget your hiking boots!

Multi level homes on a bay surrounding in foliage

Meredith, NH (107 miles, 1 hour 45 mins)

If you’re in the mood for a relaxing day on the water, head to Meredith and explore this charming town along the shores of Lake Winnipesaukee. Enjoy boating, swimming, and lakeside picnics on Waukewan Beach.

While you’re here, you can also enjoy a wine tasting at Hermit Woods Winery. Not only do they offer several great wine-tasting experiences (with excellent vino!), but they also have a fantastic restaurant onsite.

Waterway in front of a down town area with brick buildings

Providence, RI (51 miles, 1 hour 15 mins)

Providence, Rhode Island’s capital, is the perfect hub of history, culture, and culinary delights. This city has the friendliness of a small town with the attractions and sophistication of a large city. Wander through Waterplace Park and marvel at WaterFire, an art installation with 80 fire pits floating on the river, in addition to several performers.

Head to Federal Hill, Providence’s version of Little Italy when you’ve worked up an appetite. This neighborhood was once bustling with Italian immigrants, and today, it’s home to some of the best Italian food in the region. Check out Pane e Vino for fantastic pasta, steak, seafood, and Italian wine.

Lighthouse on a rock landing over looking the ocean

Newport, RI (73 miles, 1 hour 15 mins)

Famous for its stunning Gilded Age mansions lining Bellevue Avenue, Newport is a dream destination for architecture enthusiasts. Tour the opulent Breakers Mansion, built in 1895, and Marble House, completed in 1892, to be transported to the era of America’s wealthiest families.

Newport is also home to the 3.5-mile Cliff Walk, featuring ocean views on one side and Gilded Age mansions on the other. Head to the Bowman’s Warf for plenty of nautical-inspired gift shops, local New England cuisine, and sightseeing opportunities. If you’d rather hop in the water, visit Easton’s (First) Beach, King Park Beach, or Gooseberry Beach – there’s no shortage of excellent shorelines in this area.

Westerly, RI (93 miles, 2 hours)

Known for its beautiful beaches and charming downtown, Westerly invites you to relax by the ocean, explore the outdoors, and indulge in delectable seafood. Misquamicut State Beach has a large stretch of soft, powdery sand and excellent facilities like outdoor showers, concession stands, a playground, and bathrooms.

Wilcox Park is another beautiful outdoor spot in Westerly, boasting scenic walking paths, lush gardens, impressive sculptures, and a lovely fountain. Afterward, indulge in a lobster roll at one of the many restaurants around town, including Two Little Fish, The Cooked Goose, and Windjammer Surf Bar.  

Head to the affluent Watch Hill neighborhood (the one Tayloe Swift calls home) to admire the mansions on the coast, walk to the Watch Hill Lighthouse, and take a waterfront stroll through downtown. There are plenty of boutique shops and dining options to cap off your day.

Bristol, RI (65 miles, 1 hour 15 mins) 

Bristol is a quaint coastal town in Rhode Island with a rich history and deep seaport. Visit the Blithewold Mansion, Gardens & Arboretum, an expansive summer estate initially built for the Augustus Van Winkle family. This English-style manor sits on 33 acres of land, featuring ten different gardens and 500 different plants. 

For more outdoor excursions, Colt State Park is another popular attraction. This 464-acre park sits on Narragansett Bay, so you can walk or bike along the water and explore the open fields with historic stone walls.

Cape Elizabeth, ME (118 miles, 2 hours)

Cape Elizabeth is best known for its iconic Portland Head Light lighthouse. However, this isn’t the only lighthouse in the area. Embark on a self-guided lighthouse tour to visit Portland Head, Ram Island Ledge Lighthouse, and Two Lights, a set of twin lights.

For a bit of relaxation, take a walk along Crescent Beach and revel in the serenity of nature. This beach has soft sand, a quiet atmosphere, a snack bar, and a bathhouse, so you could easily spend the entire day here.

Portsmouth, NH (56 miles, 1 hr)

Portsmouth exudes New England charm with its brick sidewalks, historic houses, and bustling waterfront. Explore the open-air museum, Strawbery Banke Museum, nestled in the oldest neighborhood in New Hampshire, Puddle Dock. This living history museum comprises 10 acres of land and depicts the 1600s through the 1900s. 

Enjoy even more history along the Portsmouth Harbor Trail, which winds through the city and leads you to 70 different historic and scenic points. You’ll see sites like the USS Albacore, Memorial Bridge, and more along the way.

Kennebunkport, ME (90 miles, 1 hour 30 mins)

Kennebunkport is the epitome of coastal beauty, boasting charming boutiques, art galleries, and stunning beaches. The long and sandy Goose Rocks Beach is an excellent place to spend an afternoon and is likely the most scenic shore in Kennebunkport.

St. Ann’s Episcopal Church, an old stone church with ocean views, is open for tours to see the historic architecture and grounds. Another popular attraction is the Seashore Trolley Museum, showcasing exhibits on old trolleys, buses, and other historic vehicles.

Kittery, ME (59 miles, 1 hour)

With a 400-year-old history, Kittery is the oldest town in Maine, making this a paradise for history buffs. Check out Fort McClary State Historic Site, a 300-year-old fort that housed American soldiers during five different wars. 

For the ultimate shopping day, explore the Kittery Premium Outlets, offering great deals on popular brands, high-end names, and locally sourced goods. The most popular store at this outlet is the Kittery Trading Post, a three-story shopping experience offering everything from camping and fishing goods to skiing and snowboarding equipment.

York, ME (70 miles, 1 hour 15 mins)

York, Maine, is one of the best day trips from Boston – you can explore the rugged beauty of Cape Neddick and the famous Nubble Lighthouse. Stroll along Long Sands Beach, popular for swimming, surfing, and sand volleyball, then savor fresh seafood at one of the local restaurants. I recommend Lobster Cove or Fox’s Lobster House!

Portland, ME (112 miles, 1 hour 15 mins)

As Maine’s largest city, Portland offers a vibrant culinary scene, a lively arts community, and a picturesque waterfront. In recent years, this city has been dubbed a “hipster’s paradise” due to the emphasis on contemporary art and locally sourced food. 

Explore the Old Port District, home to Portland’s oldest buildings, and browse the many boutiques, bars, and restaurants lining the cobblestone streets and waterfront. 

Freeport, ME (122 miles, 2 hours)

A shopaholic’s paradise, Freeport is home to the famous L.L.Bean flagship store and numerous outlets with over 170 retailers like Banana Republic, Nike, Coach, and Tommy Hilfiger. Must-visit local shops include Cotton Weeds Quilt Shop, Abacus Gallery, and Georgetown Pottery

If you still have time after all that shopping, explore the scenic coastline at Wolfe’s Neck State Park, home to over 5 miles of paths, 230 acres of land, and the rocky shores of Casco Bay.

Salem, MA (17 miles, 45 mins) 

With its fascinating history, Hocus Pocus shooting locations and captivating museums, Salem is a must-visit day trip from Boston. Delve into the town’s eerie past at the Salem Witch Museum and explore its maritime heritage at the Salem Maritime National Historic Site

Other popular attractions include the Peabody Essex Museum, with over 840,000 words of art, and the House of the Seven Gables, made famous by Nathaniel Hawethorne’s novel of the same name. With so much to do, you could spend more than a day in Salem!

Rockport, MA (39 miles, 1 hour)

Rockport’s beautiful harbor, art galleries, and charming Bearskin Neck make it a delightful seaside town. You can pick up pottery, jewelry, and homemade fudge as you stroll through Bearskin Neck, an area showcasing several local shops in former fishing shacks. You won’t find big-box retailers in this neighborhood – only the local goods!

You can also explore the 30 art galleries throughout Rockport or head to one of the quaint beaches, including Front Beach, Long Beach, and Cape Hedge. You’ll love the charming seaside atmosphere in this quintessential New England town.

Plymouth, MA (41 miles, 1 hour)

For an entire day of history, a day trip to Plymouth does not disappoint. Step back to the early 17th century at Plimoth Plantation, where costumed interpreters bring history to life. Also known as the Plimoth Patuxet Museum, this living history museum has exhibits on the Mayflower, a 17th-century English Village, and the Plimoth Grist Mill. 

You can also visit Plymouth Rock, a symbol of the Pilgrim’s arrival on the Mayflower, located in Pilgrim Memorial State Park.

Sandwich, MA (59 miles, 1 hour 15 mins)

Sandwich is the oldest town on Cape Cod and boasts a treasure trove of historic sites and scenic vistas. Explore the Sandwich Glass Museum, where you can view a glass-blowing demonstration, then visit the Heritage Museums & Gardens, home to 100 acres of land, several trails, and a 200-year-old windmill.

Town Neck Beach is another excellent spot in Sandwich to unwind and connect with nature. Pack a picnic and enjoy a walk along the shore!

Falmouth, MA (73 miles, 1 hour 30 mins) 

Enjoy a day soaking up the sun and splashing in the water in Falmouth, Massachusetts. The clear waters of Buzzards Bay and Vineyard Sound are warmed by the Gulf Stream, making this an excellent spot for swimming.

Falmouth also has one of the best Main Streets in Cape Cod for shopping. You’ll find everything from souvenir shops to bookstores, jewelers, and home decor stores. One of my favorites is Homespun Garden – they have some really unique decor pieces!

Within Falmouth, you’ll find the small village of Woods Hole, where you can enjoy incredibly scenic oceanfront areas like Trunk River and Nobska or access the Shining Sea Bikeway for a beautiful bike ride. More notably, you can also visit the Woods Hole Oceanographic Institution, a world-class aquarium and research facility.

The cozy and fun seaside town of Martha’s Vineyard is only a 35-minute ferry ride from Falmouth. The island makes a perfect day trip from Boston to enjoy lighthouses, charming harbor towns, and plenty of sandy beaches. If you visit from April through October, you can even join a whale-watching tour to see the migrating humpbacks, finbacks, orcas, and pilot whales.

Provincetown, MA (117 miles, 2 hours or 95 min ferry) 

Provincetown, at the tip of Cape Cod, is known for its vibrant art scene, beautiful beaches, and stunning sunsets. While you can drive two hours to this adorable town, you can also hop on a ferry from Boston for an even shorter journey, around 95 minutes.

Explore the bustling Commercial Street, where you’ll find several specialty shops, cabarets, art galleries, and restaurants. On the east end of this street, you can spend some time at the Provincetown Museum of Art, showcasing the work of several Cape Cod artists.

Sturbridge, MA (60 miles, 1 hour 15 mins) 

A little over an hour from Boston, Sturbridge is most notable for its living history museum. Travel back in time to Old Sturbridge Village, recreating rural New England life between the 1790s to the 1830s. Located on 200 acres, this museum has 40 historic buildings, several costumed historians, and a collection of over 40,000 artifacts.

Lexington, MA (15 miles, 30 mins) 

Experience American history firsthand in Lexington, where the first shots of the American Revolution were fired. Visit the Minute Man National Historic Park, where you’ll find the Minuteman Statue and Revolutionary Monument; this park is the perfect spot to learn about the beginnings of the Revolutionary War. Nearby, the Hancock-Clarke House provides information on the role of this town during the revolution.

Small light house and Cap Cod style homes on a sandy beach

Barnstable, MA (71 miles, 1 hour 30 mins)

Barnstable, Massachusetts, offers quintessential Cape Cod experiences, like beautiful beaches and whale-watching opportunities. Nearby Hyannis village and seaport have a lot of personality with tourist shops, local galleries, restaurants, and ice cream shops. If you visit between April and October, book a whale-watching tour with Hyannis Whale Watcher Cruises

If you’d rather stay on land, the Coast Guard Heritage Museum offers a highly informative tour and well-preserved United States Coast Guard artifacts.

Yarmouth, MA (76 miles, 1 hour 30 mins)

Yarmouth is an ideal destination for those seeking relaxation by the ocean. Enjoy peaceful beaches and explore the cultural exhibits at the Cultural Center of Cape Cod – this center boasts five galleries, a pottery studio, five resident artist studios, and a culinary center. 

The Whydah Pirate Museum is the perfect day activity for the entire family. This interactive exhibition is the only one in the world to showcase authentic pirate treasure!

Yarmouth is also a great place to enjoy a day at the beach. On Nantucket Sound, Seagull Beach is Yarmouth’s largest and most popular beach, with 2,000 feet of powdery, soft sand, a snack bar, and well-maintained bathrooms.

Plum Island, MA (43 miles, 1 hour 22 mins)

As a barrier island off the coast of Massachusetts, Plum Island, named after the beach plums that grow wild on its dunes, is perfect for a retreat from the city. Nature enthusiasts will love Plum Island’s wildlife refuges and stunning barrier beaches like Plum Island Beach. Birdwatchers can spot various bird species at the Parker River National Wildlife Refuge.

You can also visit Newburyport Harbor Light, the Plum Island Lighthouse. Afterward, order a lobster roll at Bob Lobster, a fish market and seafood shack connecting Plum Island to Newburyport on the turnpike.

Marblehead, MA (16 miles, 45 mins)

Marblehead is one of the oldest coastal towns in New England. While you’re here, go on a historic home walk – you can wander through the historic district and admire the colonial architecture. There are over 300 homes that date back to the 17th and 18th centuries!

This town also houses a beautiful cemetery, Old Burial Hill. Established in 1638, this cemetery contains the graves of 600 revolutionary heroes, including General Jonathon Glover. Another notable graveyard citizen is Wilmot “Mammy” Redd, who was executed for witchcraft during the Salem witch trials.

Worcester, MA (47 miles, 1 hour)

Worcester offers a mix of cultural attractions, including the Worcester Art Museum and Ecotarium, making it a great day trip from Boston for families. The EcoTarium boasts a digital planetarium, a narrow-gauge railway, and several animal exhibits.

The Worcester Art Museum is another fantastic museum featuring Impressionist paintings, Roman mosaics, and medieval armor. When you’re not exploring Worcester’s museums, its streets are equally as fascinating. You’ll notice Victorian-era mill architecture, three-story 19th-century homes, and several lunch car diners!

Manchester by the Sea, MA (30 miles, 1 hour)

Relish the scenic beauty of Manchester by the Sea, a lovely coastal town featuring sprawling homes perched on rocky shores, elaborate summer cottages, and stunning seaside resorts. 

Spend a relaxing day at Singing Beach, aptly named as the sand “sings” when you walk on it. When sand is dry enough, the grains are just the right size, and the sand contains silica, it creates a bit of a “squeak” as you shuffle across the beach. 

Many visitors to this area enjoy sailing around Cape Ann. You can get an incredible view of the rugged coastline, gorgeous beaches, and massive homes from the water.

Stonington, CT (100 miles, 1 hour 40 mins)

Stonington, CT, located about 100 miles from Boston, is a charming coastal town that captivates visitors with its historic architecture, beautiful waterfront, and serene atmosphere. 

For a more laid-back experience, spend more time in Stonington Borough, a quaint village known for its narrow streets lined with historic homes, art galleries, and boutique shops. Nature enthusiasts can also enjoy the scenic beauty of Stonington Point, a picturesque spot to watch the sunset over the water.

Mystic, CT (1 hour 45 mins)

One of the main attractions near Stonington is Mystic, a neighboring village renowned for its maritime heritage and home to the famous Mystic Seaport, the largest maritime museum in the United States.

Visitors can explore the 19th-century seafaring village, climb aboard historic ships, and interact with costumed interpreters. There are plenty of fun activities, scenic views, shopping, and dining in downtown Mystic that make for a great day trip from Boston.

Essex, CT (125 miles, 2 hours)

Essex, a charming town in Middlesex County nestled along the Connecticut River, is known for its boating, fishing, scenic beauty, and picturesque appeal. There are plenty of recreational activities along the riverfront and sweet and savory cafes (Savour Cafe & Bakery is my favorite) to satisfy your sweet tooth. A walk down Main Street in Essex Village is a great way to spend a few hours with its well-manicured homes, charming streets, unique shops and boutique inns. This scenic village makes a fantastic day trip from Boston or a lovely weekend getaway.

White light house on the coast surrounded by colonial style houses

New London, CT (113 miles, 1.5 hours)

Every summer, New London, Connecticut, comes to life with street musicians, boat cruises, outdoor fountains, and lovely al fresco dining. The main attraction, Ocean Beach Park, has been voted one of the best beaches in Connecticut, and it’s no surprise why. With soft sand, bright blue Atlantic waters, a half-mile-long boardwalk, and several cafes and concession stands, this beach makes a fantastic summer day trip from Boston. 

Explore New London’s Historic Waterfront District, a 26-block neighborhood lined with over 30 restaurants, countless shops, and performing arts venues. Simply strolling around this creative hub is a fun afternoon activity – over 220 historic buildings are located within this district. Stop for a delicious meal at On the Waterfront, then afterward, grab something sweet at Michael’s Dairy

Hartford, CT (100 miles, 1.5 hours)

Connecticut’s capital, Hartford, offers a blend of modern city life and historical landmarks; while you’re here, you can enjoy lush green spaces, yummy eats, and a vibrant cultural scene. 

Start at the Mark Twain House & Museum – this 19th-century Victorian Gothic home was where this author lived between 1874 and 1891. Take a guided tour, marvel at the 16,000 artifacts, and learn about “the father of American literature.”

On a warm day, check out Elizabeth Park, home to 100 acres of gardens, green spaces, and roses. The south border of this park is known as the nation’s first municipal rose garden and has over 800 kinds of roses. The rose archways, wooden gazebo, and sweet floral scent will make you feel like you’ve been transported into a fairy tale!

Visiting the Connecticut State Capitol is a must while you’re in Hartford. You can go on a guided or self-guided tour of this building to learn more about Connecticut’s history and view the chambers.

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Boston is so much fun in its own right, but with so many popular destinations, quaint towns, and charming seaside villages to explore, you’ll have no trouble enjoying a day trip from Boston. 

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One Comment

  1. You have done a great job of highlighting some of the best and most unique places to visit near Boston. I like how you explained the attractions and activities of each destination in a clear and concise way, with some links and resources for more information. You also gave some practical suggestions and recommendations on how to plan, prepare, and enjoy your trip. Your photos are amazing and inspiring, too. They make me want to visit these places myself and experience their beauty and charm.

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