A Local’s Favorite Day Trips from Boston

Planning day trips from Boston can be overwhelming if you don’t know where to start. But with this guide, you’ll be able to easily experience New England’s charm, nature, and the rich history that lies just outside the city. 

I’m a Boston area local who loves exploring nearby destinations. I am here to share my favorite places to visit in Massachusetts and around New England. 

There’s a Boston day trip on this list for everyone. We’ll cover iconic landmarks, adventures on the water, historic towns, and escapes to nature. Let’s dive in!

Affiliate Disclosure: Travel Lemming is an independent reader-supported blog. You can support us by purchasing via the affiliate links on this page, which may earn us commissions. See our Advertising Policy for further explanation. Thank you!

23 Best Boston Day Trips

The Berkshires, Massachusetts

This rural area is known for its natural beauty and outdoor recreation year-round. 

🗺️ Distance from Boston: 2-hour Drive | 📍Google Maps | The Berkshires Website

The Berkshires are a rural area located in Western Massachusetts. There is so much to do and explore in this part of New England. 

The Berkshires are for nature lovers. This highland region has beautiful, diverse terrain. From lush forests to mountain views, blue lakes, and colorful foliage – there’s plenty of adventure.

Enjoy the natural beauty of the Berkshires all year round. Go cross-country skiing in the winter and hike Mount Greylock in the summer. 

There is also a big art community in these historic villages. Check out the Norman Rockwell Museum in Stockbridge. You can also catch the Boston Symphony Orchestra at Tanglewood during their summer residency. 

If you want to extend your day trip to a weekend getaway, see Meg’s guide to where to stay in the Berkshires.

Salem, Massachusetts

Made famous by the 1692 Salem witch trials, Salem offers spooks, art, history, and family-friendly games.  

🗺️ Distance from Boston: 45-minute Drive | 📍 Google Maps | Salem City Website

Salem is one of the most popular day trips from Boston during the fall. It is well known for its historic sites of the 1692 Salem witch trials. Salem is home to the wickedly wonderful Sanderson sisters, the House of the Seven Gables, the Salem Witch Museum, and the Witch House.  

But this seaside town is so much more than just witches. Visit the world-class Peabody Essex Museum (PEM), the longest continuously-running museum in the country. The Peabody Essex Museum has something for everyone, whether you like to be spooked or not. 

Not interested in an art or history lesson? Beat the high scores at the Salem Willows Arcade. The harborside park is packed with vintage games, which gives it a nostalgic vibe. The arcade also features mini-golf, a few rides, and all the greasy foods you can only find at an amusement park. 

Woodstock, Vermont

Charming Woodstock is a paradise for leaf-peepers and foodies. 

🗺️ Distance from Boston: 2 hours, 15 minutes | 📍 Google Maps | Woodstock City Website

Woodstock is a small charming town surrounded by green mountains and babbling streams.

Woodstock has some beautiful covered bridges that are worth a visit. The Middle Covered Bridge is located in the heart of downtown Woodstock. This lattice-truss bridge is probably the most photographed bridge in the area. Park your car in town and explore the Middle Covered Bridge on foot. 

Sample tasty cheeses at Sugarbush Farms for free. This farm is the maker of award-winning cheddar cheese and maple syrup. If you’re a foodie, this stop is a must! Visit with the cows and wander in the woods. Enjoy this little slice of Vermont heaven.

Concord, Massachusetts

This city seamlessly intertwines history, culture, and nature. 

🗺️ Distance from Boston: 35-minute Drive | 📍Google Maps | Concord Website

Concord is just a 30-minute drive Northwest of Boston. It’s home to some American Revolutionary War sites, such as the Old North Bridge – where a key battle took place. 

The Minute Man National Historic Park features 970 acres of land, trails, exhibits, and monuments. It spills into Concord, Lexington, and Lincoln.

There are other interesting things to do in Concord for the entire family. Activities include music, theater, museums, and access to nature. This town is easy to navigate on foot or by bike, with beautiful scenic river views.

White Mountain National Forest, New Hampshire

An expansive natural wonder offering year-round activities and an escape from city life. 

🗺️ Distance from Boston: 2-hour Drive | 📍 Google Maps | White Mountain National Forest Website

White Mountain National Forest (WMNF) is a federally managed forest within the states of New Hampshire and Maine. The region is known for its high peaks, including Mount Washington. It is a good Boston day trip if you’re looking for breathtaking scenery and wildlife.

I got to enjoy a family hike over the summer on this day trip. We hid underneath the shade of the trees as we walked a beginner-friendly trail. We also got to splash and cool off in its mountain-clear streams. Yet, this doesn’t scratch the surface of what the 800,000 acres of wilderness offer. 

White Mountain National Forest offers outdoor fun in all seasons. In summer, go biking, fishing, climbing, stargazing, bird watching, or scenic driving. You can always admire the bright foliage on a hike or drive during the fall. Enjoy skiing over the winter. And finally, go camping during the spring and summer.

Sturbridge Village, Massachusetts

History runs deep in the town of Sturbridge, featuring dozens of historic buildings and a massive flea market. 

🗺️ Distance from Boston: 1-hour Drive | 📍 Google Maps | Sturbridge Village Website

Sturbridge offers small-town charm in the heart of New England. It’s home to many historical sites and plenty of outdoor activities. Sturbridge offers over 30 miles of hiking trails for nature lovers. 

The most popular attraction in Sturbridge is the Old Sturbridge Village, a historical living museum. It is a recreated 1830s rural New England Town. You can explore more than 40 historic buildings and interact with costumed historians. You will be inspired by the stories of the early 19th century and see tasks from the past at work. 

Peruse through three levels of bargains at the Sturbridge Flea Market. This iconic flea market is housed in a mill from the 1800s. It has three floors packed with vendors. You will find everything from antique jewelry to appliances.

Lexington, Massachusetts

The birthplace of the American Revolution, Lexington is an iconic destination for history lovers. 

🗺️ Distance from Boston: 30-minute Drive | 📍 Google Maps | Lexington Website

Lexington is the birthplace of the American Revolution and is only half an hour from Boston. It is rich in cultural activities, history, charming shops, and restaurants. 

Start your journey with a ride on the Liberty Ride Trolley Tour. The little trolley travels along sites of Revolutionary War history. On the tour, volunteer guides tell the story of each historical attraction. The trolley is also a convenient way to get around the city. You can hop on and off at any of the sites with free reboarding. 

A popular stop on the trolley tour is the Lexington Green. This is where the first shot of the American War of Independence was fired in 1775. You can see the 18th-century buildings still standing as well as the Minute Man Statue.

Plymouth, Massachusetts

Explore where the Mayflower came ashore more than 400 years ago at Plymouth. 

🗺️ Distance from Boston: 1-hour Drive | 📍 Google Maps | Plymouth City Website

Plymouth is a perfect day trip from Boston for history lovers. Plymouth was founded in 1620 and is the site of the first Pilgrim settlement, and where you will also find Plymouth Rock. Mayflower II is a replica of the Mayflower that carried over 100 settlers to the Wampanoag people’s land. It is anchored in the harbor. 

Learn about the country’s history in live action with Plimoth Patuxet Living History Museum. The tour will take you back to a day in the life of the Pilgrims and Pokanoket people. In this living history museum, stories are read by role-playing actors. You can even take a walk through an actual English Pilgrim settlement as well as a trip aboard the MayFlower II.

Arnold Arboretum, Massachusetts

Escape to nature without needing a car or having to go far from the city of Boston.

🗺️ Distance from Boston: 30 minutes | 📍 Google Maps | Arnold Arboretum Website

Don’t have a car to drive out of the city and enjoy a day in nature? This final entry on my list of day trips is for you. Harvard’s Arnold Arboretum is a 281-acre park that is home to over 16,000 hardy trees, shrubs, and vines. 

The free public park is located in the Jamaica Plain and Roslindale neighborhoods. Commuters using public transportation can easily access it from Boston. You can grab one of Boston’s blue rental bikes, zoom across the city, and enter one of the eight entrances. 

I have enjoyed the beautiful landscapes of this arboretum countless times. Peters Hills is the highest point on the grounds and my favorite spot in the arboretum. It provides the most glorious view of the Boston skyline. 

Harvard Arboretum is completely free to visit and is open to the public from sunrise to sunset. To avoid getting lost, you can download the Expeditions app. It features a map that will help guide you along trails with audio tours.

Providence, Rhode Island

This city offers small-town charm with big-city culture. 

🗺️ Distance from Boston: 1-hour Drive | 📍Google Maps | Providence Website

Providence is the Capital of Rhode Island. It is a vibrant city that blends historic charm, diverse neighborhoods, a thriving art scene, and a growing culinary reputation.

This coastline city offers plenty of outdoor recreation like walking, biking, and boating. Explore the cobblestone streets and take in the historical architecture. The Rhode Island State House is an architectural gem known for its grand dome. 

Providence has a youthful and lively energy. Head to Federal Hill, an Italian-influenced neighborhood. This area is known for its culture and vibrant restaurants.

Newburyport, Massachusetts

A small coastal city packed with all the charm of a Quintessential New England town. 

🗺️ Distance from Boston: 1-hour Drive | 📍 Google Maps | Newburyport City Website

Newburyport is a coastal city located northeast of Boston, nestled where the Merrimack River meets the Atlantic Ocean. This Newburyport historic district is known for its old-time charm, rich history, and scenic beauty. 

The downtown Waterfront Park is a great place to stroll on its scenic boardwalk. It runs along the Merrimack River and is an excellent spot to relax, people-watch, and take in the view of all the fishing boats. The boardwalk even features a few outdoor art installations. 

Newburyport is known for its waterfront dining scene. Grab something to eat at Tuscan Sea Grill & Bar. They specialize in artisan coastal Italian cuisine. It is a beautiful location right on the water with a warm ambiance. They have incredible food and drinks paired with breathtaking waterfront views.

Gloucester, Massachusetts

One of the nation’s top fishing ports, Gloucester offers beaches and whale-watching tours.

🗺️ Distance from Boston: 45 minutes | 📍 Google Maps | Gloucester Website

Gloucester is a coastal town about 45 minutes from Boston. It is one of America’s oldest fishing ports and is rich in seafaring tradition. Gloucester offers maritime history, fresh-caught seafood, several beautiful beaches, and an active working waterfront. 

I love a good adventure out at sea. My favorite activity in Gloucester is whale watching. I’ve been able to see humpback whales, finback whales, dolphins, and sunfish! 

Sign up for a whale watching tour with Cape Ann Whale Watch to marvel at these majestic giants. On the tour, you will likely see whales dive, breach, lie on their back, and flap their fins.  

Gloucester is home to some incredible beaches. Check out Good Harbor Beach, the perfect spot to spend a summer day. It offers soft white sand and a large area to spread out. Even during the off-season, you can still enjoy the beach and go for a walk or run.

Kennebunkport, Maine

Kennebunkport is a historic fishing village transformed into a seaside tourist destination.

🗺️ Distance from Boston: 1 hour, 35 minutes | 📍 Google Maps | Kennebunkport City Website

Kennebunkport is a dreamy place to relax and unwind. It’s known for its beaches, lighthouses, and fresh local seafood.

One of the top things to do is to visit the bustling center of Kennebunkport. Dock Square is filled with great shopping, remarkable restaurants, and more. You can’t leave without trying the local seafood. Order a lobster roll and some fried clams at the Clam Shack. 

Want to get on the water? Consider a fishing or lobster expedition for an unforgettable experience. Or go sailing. In this luxury catamaran sailing tour, you can cruise along the waters in a spacious catamaran.

Crane Estate in Ipswich, Massachusetts

This luxury summer home features 2,100 acres of land and is surrounded by stunning views of the sea.

🗺️ Distance from Boston: 1-hour Drive | 📍Google Maps | Castle Hill on the Crane Estate Website | General Admission: $10 Adult, $5 Child, $5 Active Military or Veteran

The Crane Estate is one of the most iconic homes on the Eastern Seaboard in Ipswich, Massachusetts. It’s a 19th-century home set on an extraordinary property and surrounded by stunning views of the sea.

This was once the summer home to Chicago tycoon Richard Crane and his family. The property features a 59-room mansion called Castle Hill, Crane Beach, and Crane Wildlife Refuge.  

Garden lovers can leisurely explore the Italian Garden and Rose Garden. You can take a guided or self-guided tour of the beautiful grounds or relax and have a picnic on the expansive lawn. Hike through the beach trails, boardwalks, dunes, and marshes.

Rockport, Massachusetts

Rockport will take your breath away with its rocky shores, lighthouses, and charming downtown. 

🗺️ Distance from Boston: 55-minute Drive | 📍 Google Maps | Rockport City Website

Rockport is located north of Boston and is a perfect place for a day of relaxation. Rockport is full of intriguing history and beauty, along with a sense of serenity. This seaside town is a wonderful getaway and is one of my personal favorite day trips.

I love to stroll through the charming and eclectic downtown. Bearskin Neck is a one-of-a-kind shopping experience. Explore the quaint shops to find handcrafted jewelry, art galleries, locally made crafts, and specialty-housed items.

You’ll also find a ton of recreational activities to do around Rockport. Go swimming, diving, sailing, or kayaking. And don’t miss the most magical sunsets at Thacher Island’s Twin Lighthouses.

👉 Read Next: Best Things to Do in Massachusetts

Portland, Maine

Maine’s most populous city enchants with cobblestone streets, chic shopping, and nautical history. 

🗺️ Distance from Boston: 1 hour, 45 minutes | 📍 Google Maps | Portland City Website

Portland is a city set on the peninsula of Maine. This coastal area is popular during the summertime. Tourists enjoy having access to its beaches, forests, and other landscapes. 

Experience the charming Old Port, a revitalized warehouse district. The old brick buildings have been transformed into restaurants, shops, and apartments. The area is now known for its chic shopping, renowned dining, and bustling nightlife. 

Nautical buffs will enjoy a climb to the Portland Observatory. The observatory was built in 1807 and is the last wooden signal tower in North America. It offers great views of Portland, Back Cove, Casco Bay, and Mt. Washington.

Nantucket, Massachusetts

Nantucket makes a long day trip highlighted by blinking lighthouses and a charming pace of life. 

🗺️ Distance from Boston: 3 hours, 45 minutes | 📍 Google Maps | Nantucket Website

Nantucket is a tiny isolated island located off the coast of Cape Cod. The island known as “The Grey Lady” is dressed in hydrangeas and salty air. Nantucket is open to visitors all year round, but becomes lively in the summer when Nantucket’s breathtaking beaches take center stage. 

Nantucket’s three lighthouses provide the ultimate Instagramable backdrop. The Brant Point Lighthouse is the shortest distance from town. You can enjoy it with views of the harbor. 

The Bluff Walk offers visitors an experience reminiscent of the classic fairytale The Secret Garden. The public walkway runs through the backyards of iconic Nantucket homes. Hike through gardens and lattice archways as you take in the views of the Atlantic Coast. 

Plum Island, Massachusetts

Enjoy a day trip in a big sandbox with scenic views covering the coastline.

🗺️ Distance from Boston: 1-hour Drive | 📍 Google Maps | Plum Island Beach Website

Plum Island is located right on the coast of Massachusetts. The barrier island is 11 miles long with breathtaking views.

Visit Parker River National Wildlife Refuge. This sanctuary takes up most of the land on the Island. People visit the area for bird watching due to the number of migratory birds in the area. The sanctuary is open every day of the week from sunrise to sunset. 

Don’t forget to snap your photo at the Pink House! The Pink House is one of the abandoned historic homes you will find throughout Massachusetts. People refer to it as the Plum Island Pink House. It is hard to miss as it is located right off of the Plum Island Turnpike.

Newport, Rhode Island

Newport is a city of living history, opulent mansions, and yacht-filled harbors.

🗺️ Distance from Boston: 1 hour, 30 minutes | 📍 Google Maps | Newport City Website

Newport is one of the best day trips for a coastal getaway near Boston. Newport is a town rich in history. It features miles of scenic coastline, colonial-era architecture, art galleries, and charming shops. 

Explore the Cliff Walk, a beautiful trail that runs 3.5 miles along the coast. It will take you along the stunning coastline, historic mansions, and rocky beaches of Rhode Island. Parts of the trail are paved, while other parts have a rocky shoreline. Either way, you can still enjoy the scenic ocean views. 

Take a family-friendly self-guided tour at the Newport Mansions. Each of the mansions offers a step back in time. The Elms, Marble House, Rose Cliff, and Breakers were all once known as “summer cottages.” Parking is free at all mansions.

Martha’s Vineyard, Massachusetts

The famous summer getaway, Martha’s Vineyard, is just a fun ferry ride from Cape Cod.  

🗺️ Distance from Boston: 2 hours, 40 minutes | 📍 Google Maps | Martha’s Vineyard Website

Martha’s Vineyard is a world away from the hustle and bustle of Boston. This island is just 7 miles off the coast of mainland Massachusetts. This famous New England summer colony is accessible only by ferry or by air.

Visit the quirky and photogenic Oak Bluffs. The campground is a collection of Victorian gingerbread cottages. The cottages are privately owned. But you can still enjoy the charming candy-colored exteriors. Keep an eye out for the Grand Illumination in August. Each porch is hung with Japanese lanterns. 

The most iconic lighthouse in the Vineyard is the Edgartown Lighthouse. You will find plenty of photo opportunities from the ground. It is surrounded by a backdrop of greenery and flowers. You’re in for a special treat when you climb to the top of the lighthouse. The reward is breathtaking views of the surrounding area of Martha’s Vineyard. 

Cape Cod, Massachusetts

Cape Cod has more than 500 miles of warm sandy beaches and stunning coastlines. 

🗺️ Distance from Boston: 1 hour, 30 minutes | 📍 Google Maps | Cape Cod City Website

Cape Cod is the hooked-shaped peninsula of the state of Massachusetts. Cape Cod is one of the most popular summertime day trips near Boston. Visit for picturesque ocean beaches, seafood shacks, and lighthouses. There are so many fun things to do here.

I love the serene beaches in Cape Cod. It feels as if I have left Massachusetts without ever setting foot outside of the state. There is nothing like relaxing on the warm sandy beaches. 

Do you need more adventure? Explore the many hiking and biking trails along the Cape Cod National Seashore, which offer scenic landscapes. 

See our guide to the best areas & hotels to stay in Cape Cod if you want to extend your day trip to a weekend (or longer).

👉 You Might Also Like: My fall getaway at AutoCamp Cape Cod

Hampton Beach, New Hampshire

Hampton Beach is one of the widest beaches on the Atlantic coast. 

🗺️ Distance from Boston: 1-hour Drive | 📍 Google Maps | Hampton Beach Website

Hampton Beach is a popular Boston day trip due to its lively boardwalk. The Hampton Beach boardwalk is lined with souvenir shops, ice cream parlors, and arcade games.

Hampton Beach features a full season of entertainment and activities for all ages. There’s so much outdoor exploration to do outside the Marina.

Go paddle boarding through the marshes and take part in deep-sea fishing. End a day of fun in the sun with a splendid sunset over the water. 

Lincoln Ice Castles, New Hampshire

A must-see winter phenomenon, featuring frozen castles and family-friendly winter activities.

🗺️ Distance from Boston: 2-hour Drive | 📍 Google Maps | Lincoln Ice Castles Website | General Admission: $29 (12 and up), Ages 4 to 11: $22

Boston is renowned for being a winter wonderland. But north of the city lie magical ice castles that resemble something straight out of the Disney movie, Frozen. 

The Lincoln Ice Castles make for one of the best day trips for families during winter. This frozen attraction brings fairy tales to life for all ages. 

To visit the Lincoln Ice Castles, put on all of your layers and head to the mountains of New Hampshire. The castles include lit-up sculptures, frozen thrones, ice-carved tunnels, slides, and fountains. This location also offers snow tubing, sleigh rides, and a mystical light walk through an enchanted forest. 

The Ice Castles are open seasonally, with the exact date depending on Mother Nature. Plan ahead and buy your tickets in advance online. 

***

Boston’s prime location makes it convenient to explore other parts of New England and its historic towns. Check out my guide to where to stay in Boston as you plan your trip to Massachusetts.