Summer in Massachusetts means long, sunny days, blue skies and endless possibilities for exciting summer day trips. It can also mean traffic, and a lot of it! With both locals and tourists trying to navigate all around Greater Boston, it’s a no-brainer that car-free adventures are your ticket to relaxation: no worrying about driving, traffic, trying to find – and then having to pay for – parking. Leave the car behind and spend a day lounging at a local beach, paddling along the coast, or exploring Massachusetts’ hidden gems. There’s no shortage of quick getaways just a short ride from Boston. Whether you’re flying solo, planning a fun day with your bestie, or looking for a couple’s adventure, we’ve rounded up the best summer day trips you need to take!
Visit Local Lighthouses
Historic lighthouses and ocean views are what make summer in Massachusetts so unique. The miles of sweeping oceanfront overlooked by remarkable beacons of light are iconic, representing our heritage and culture. Photographers will love to capture these historic lights from afar, while those looking for history or a thrill will want to tour, and maybe even climb up a lighthouse! We recommend planning a lighthouse adventure for a quintessential New England summer experience. From the Twin Lights on Thacher Island off the coast of Rockport, to Eastern Point Lighthouse in Gloucester and Race Point Light in Provincetown, each light is unique and tells its own story. For our full guide on these stunning landmarks, check out our blog The Best Lighthouses in Massachusetts to See This Summer!
If you’re looking for a fully planned day trip – including transportation from Boston – to easily see some of these lighthouses check out our tours! The Baker Island Boat & Lighthouse Tour in Salem offers you a relaxing boat ride to the exclusive Bakers Island where you’ll meet the keeper and tour Bakers Island Light. For the ultimate thrill-seekers, check out our Kayak & Hike Adventure to Historic Thacher Island. You’ll kayak across the open ocean to Thacher Island, hike the island’s beautiful nature trails, and even visit one of the only operating twin lights in the United States.
Skip the traffic & Ride the Cape Flyer to to Cape Cod
Hop on board the Cape Flyer for an easy, stress-free way to get to Cape Cod. You can board in Boston, Braintree, or anywhere else along the way to skip the driving and traffic headache. Spend the day, or weekend, exploring Hyannis’ shops and restaurants. Venture out to the Cape Cod National Seashore, where the waves crash onto beautiful white sand beaches. A visit to Cape Cod isn’t complete without a visit to an old-fashioned seafood shack; you’ll savor golden brown, delicious fried clams, oysters, fish and more, some even serve up cool ice cream treats to round out your meal! This is one of the easiest and most scenic day trips from Boston by train. You can also find transportation connections to Outer Cape (including Wellfleet & Provincetown) and the islands of Martha’s Vineyard and Nantucket at various stops along the way; see the Cape Flyer website for more details.
Celebrate the 50th Anniversary of Jaws
Shark lovers, rejoice! 2025 marks 50 years since Jaws first terrified moviegoers, and you can join the fun with special exhibits, events, outdoor screenings of the film and tours on the Cape. Through September 7th, 2025, the Martha’s Vineyard Museum is hosting Jaws at 50: A Deeper Dive. This special exhibit brings you below the surface of the movie, into authentic movie props, behind the scenes photographs, oral histories and memorabilia. Catch a showing under the stars at an old-fashioned drive-in movie theater for a truly nostalgic experience. Dive even further into the movie, visit iconic filming locations on Martha’s Vineyard on a guided JAWS-themed tour or with the use of the SetJetters app.
Take the Ferry to Provincetown
All aboard the ferry for a quick cruise across Boston Harbor to Provincetown! Situated on the very tip of Cape Cod,P-Town (as it’s known locally) has a vibrant art scene, gorgeous beaches, delicious eats and historic sites to explore. Perfect for a spontaneous day trip or overnight getaway, P-Town is the spot to grab a mouth-watering New England lobster roll at the iconic Lobster Pot, relax at Race Point Beach or bike around town. History-buffs will want to check out Race Point Light or climb the historic Pilgrim Monument. Ferries depart from Boston’s World Trade Center by Bay State Cruises, and Boston’s Long Wharf by Boston Harbor City Cruises.
Attend a Local Fair or Festival
Celebrate summer New England-style at a local fair or festival. From chowder-fests to craft fairs and live outdoor concerts, there’s always something happening around the state. With delicious snacks, live entertainment, petting zoos, rides or midway games, each fair or festival is unique, and totally fun!
Don’t miss the largest Portuguese festival in the world, taking place right here in Massachusetts: The Feast of the Blessed Sacrament! With four days of live entertainment, mouth-watering Portuguese foods, midday games and rides, parades and Madeira wine, there’s something for everyone to enjoy at this beloved festival. Save yourself the headache of trying to drive and find parking (it’s street parking only!) and book your ticket to this show-stopping summer event with Keolis massAdventures. Your ticket with us includes round-trip transportation via Commuter Rail + Private Shuttle from the New Bedford Station to The Feast, and back, and you’ll get a $20 Meal Voucher with it, valid for any Food/Beverage at The Feast, including alcohol. For those who live in Holbrook, Taunton, Middleborough, or anywhere else along the Fall River/New Bedford line who want to attend The Feast, but not worry about driving – this is for you!
Explore Classic New England Seaside Cities & Towns
Full of historic charm and culture shaped by the sea, these places are a must-visit for every New England summer bucket list. From the South Coast, including New Bedford and Fall River, to the North Shore with towns such as Gloucester, Rockport and Ipswich, every town has its own unique taste of seaside charm.
On the South Coast, accessible via the Commuter Rail’s Fall River/New Bedford line, New Bedford and Fall River are cities whose waterfront heritage shaped and ultimately grew the cities.
Spend a Day in New Bedford
New Bedford’s whaling history goes back to the 1760s, with advantageous location along with a boom in the industry deeming it the “Whaling City” in the 19th century. It was the world’s leading whaling port and home to the largest and most advanced whaling fleet in the world. Along the whaling routes were Portuguese islands, the Azores, where men with seafaring skills were recruited to join the whaling expeditions. Many of these men later moved their families to the “Whaling City”. Immortalized in Herman Melville’s Moby-Dick, you can still visit The Seamen’s Bethel, where Melville visited before his voyage. Find out more about New Bedford’s whaling history, Portuguese heritage, and the city’s culture on your day trip with us to Explore New Bedford: Whaling Museum & Food Tour.
Climb Aboard History in Fall River
With a rich history anchored in textiles and shipbuilding; the city was also home to the luxurious Fall River Line. The Fall River Line comprised of steamships that ferried passengers between New York and Boston. Today, the city’s maritime legacy lives on in Battleship Cove. Battleship Cove holds the world’s largest collection of historic naval ships and even allows you to climb aboard and explore! Afterwards, walk down the boardwalk for stunning views of the battleships, Taunton River, and beyond. Check out the vintage Fall River Carousel and make it a true New England summer day with locally sourced seafood! The Tipsy Seagull is a fun dockside pub where you can sit or swing as you savor fresh favorites.
On the North Shore, accessible via the Commuter Rail’s Newburyport/Rockport line, Ipswich, Gloucester, Rockport and Salem emanate quaint New England town vibes, where you feel like you just might encounter an old-school fisherman around the corner.
Relax in Ipswich
With maritime roots dating back to the 1600s, Ipswich was a hub for fishing, shipbuilding and trade with Europe. Castle Hill on the Crane Estate and Crane Beach are anchored in Ipswich’s maritime legacy, since both overlook historic shipping lanes. Ipswich maritime heritage lives on through the working waterfront and commitment to coastal conservation. A relaxing coastal day in Ipswich can be found on the soft sands of Crane Beach. Whereas active day trippers will enjoy kayaking down Castle Neck River or admiring scenic views from Crane Estate’s trails. For seafood lovers, a stop at the Clam Box of Ipswich is a must!
Explore Gloucester
America’s oldest seaport, Gloucester was founded in 1623, and quickly became a major center for fishing and shipbuilding. Immortalized in The Perfect Storm, Gloucester is the real working waterfront you’ve seen on Wicked Tuna. Today, a perfect day spent in Gloucester starts with an exciting paddle in the harbor. You’ll see fishing boats in action and catch a glimpse of Eastern Point Lighthouse from your kayak seat. Stop at Ten Pound Island to admire its own Ten Pound Island Light standing tall amongst eye-catching sea glass! Reserve your spot for this thrilling, car-free kayaking adventure on our Gloucester Harbor & Annisquam River Kayak Tour. After your paddle, set out to explore the historic town. Maritime lovers and history buffs will want to visit Maritime Gloucester, the town’s maritime museum, aquarium, and working waterfront! Don’t forget to grab a bite at a dockside lobster shack for the freshest catch you’ll ever taste!
For those wanting European vibes and stunning architecture, book a day trip to Hammond Castle Museum. This breathtaking seaside castle overlooks the Atlantic Ocean and makes for an exciting day of exploration.
Enjoy Oceanfront Views in Rockport
Rockport’s maritime history is harbored in lobstering and cod-fishing. Due to its picturesque harbor scenes inspiring painters, Rockport became an artists’ colony. Today, Rockport is famous for its Motif #1, also known as the most painted building in America. The Motif #1 symbolizes New England’s maritime heritage, and specifically Rockport’s heritage by intertwining maritime and art. Today, views are still second-to-none, with painters, artists, photographers and everyone in between visiting Rockport to admire the sights. A day in Rockport should be spent soaking up the seaside vibes. For those who want to get out on the water, enjoy a relaxing adventure on our Rockport Guided Coastal Kayak or Stand-Up Paddleboarding Excursion. A day in Rockport wouldn’t be complete without a stop into a local restaurant near Rockport Harbor for amazing oceanfront views. If you’re looking for a hot, buttered lobster roll and delectable cocktails and mocktails, try The Hideaway.
Visit the Witch City
Though it’s known for the Salem Witch Trials, this seaside city is rich in maritime history. Once one of the richest ports in America, its ships brought back spices, silks and tea from the Far East. This cemented the port as a global maritime hub.
Salem Maritime National Historic Site preserves the city’s seafaring legacy, perfect for diving into history on this coastal day trip. A unique, and free, museum to check out on your day trip is the Punto Urban Art Museum. A collection of outdoor street art by Latino and immigrant citizens of Salem, this social justice public art program is truly a one-of-a-kind hidden gem in Massachusetts. In order to truly explore the coastal town and all its culture, savor favorites at local restaurants! Stop into Paprika Grill for Mediterranean, Turkish, Middle Eastern dishes. Or head to Longboards Restaurant & Bar for lobster rolls that taste as good as their harbor views look.
For those looking for more sightseeing on their day trip, check out our Bakers Island Boat & Lighthouse Tour! Climb aboard the boat for a scenic and peaceful ride across the harbor and out into Massachusetts Bay. Keep your camera ready to capture sweeping ocean views and the 5 lighthouses we’ll pass on the boat ride! Your exclusive visit to Bakers Island includes meeting the lighthouse keeper and touring Bakers Island Light Station. Explore the island after your tour or pack a picnic to enjoy by the seaside.
Book a Day Trip from Boston with Keolis massAdventures
Want to escape the city without the stress of planning, driving, or traffic? Keolis massAdventures offers curated day trips from Boston: food tours, kayaking adventures, museum tours, cranberry bog tours, and more, all with transportation from the city included. Check out some of our awesome day trips from Boston happening this summer. Each trip includes round-trip Commuter Rail transportation, plus step-by-step instructions on which train to take and which station to disembark, and no-transportation options for some that don’t want to take the Commuter Rail, and private shuttle service from your arrival station to your adventure. Some trips include added perks like entry tickets, expert-guided tours, or food vouchers!* *Food voucher is only included with New Bedford Feast of the Blessed Sacrament: Special Event Shuttle & Meal Voucher. It’s truly one of the best ways to get out of Boston to enjoy a car-free summer day trip!
No matter how you choose to explore, the best summer day trips from Boston guarantee fun, flavor and fresh perspective. Grab your sunnies, your friends, and get out there! Your next adventure is just a ride away.
