10 Amazing Massachusetts Day Trips That Are Worth The Drive
From the witch-trial history of Salem to the windswept shores of Nantucket, these ten destinations represent the very best that Massachusetts has to offer. The Atlantic coast is home to iconic hot spots like Cape Cod and Martha's Vineyard, where a trip for a bowl of chowder and a lobster roll is well worth the drive. Inland, a cruise along the Mount Greylock Scenic Byway rewards with a chance to hike the Appalachian Trail and enjoy panoramic views of New England from the highest peak in the state. The day trips listed below are all within a few hours' drive from a major urban center, and a couple even include scenic ferry rides to round out the experience. No flights and no overnight bags required, just open roads, ocean air, and the pleasure of discovering Massachusetts's greatest treasures at your own pace.
Nantucket Island
South of Cape Cod, Nantucket Island is unlike any other destination in New England. Getting there requires a one-hour high-speed ferry from Hyannis, which is about 90 minutes from Boston, but it's worth the journey. Nantucket Town is a National Historic Landmark District, and arriving here is like stepping back into the 19th century. The historic downtown, with its cobblestone Main Street and brick buildings, is protected by strict regulations that have kept the island's architecture in extraordinary condition.
Beyond the town, Nantucket Island's landscape is simply breathtaking. Its beaches are among the finest in the Northeast. Surfside Beach on the south shore catches the full force of the Atlantic swells, while the calmer north shore beaches are ideal for families who want to spend a quiet afternoon in the sun. A lobster roll at a harbor shack, followed by a sunset cocktail at the Sandbar overlooking the Nantucket Sound, makes for the kind of day you'll remember for years.
Martha's Vineyard
Martha's Vineyard is seven miles off the coast of Cape Cod. It takes about 2.5 hours to get there from Boston, and every minute of the journey is worth it. The island is divided into distinct towns, each with its own personality. Vineyard Haven, where the ferry docks, is a harbor town with a lovely main street lined with bookshops, cafés, and art galleries. Edgartown, a short drive away, is the most upscale of the towns, with Federal and Greek Revival architecture from the island's heydays.
Oak Bluffs is perhaps the most visually striking destination on the island, with its elaborately painted "gingerbread" cottages that give the neighborhood a vibe that is both surreal and delightful, like stepping into a life-sized dollhouse collection. For a more scenic view of the island, head to the cliffs at Aquinnah on the western tip, where the views are among the most spectacular in all of New England. To explore at a leisurely pace, rent a bike for the day to visit each of the towns along dedicated paths, stopping at farm stands and hidden beaches along the way.
Cape Cod
Cape Cod needs little introduction. It's perhaps the most iconic summer destination in New England, and for good reason. From Boston, you can pull into the Cape Cod National Seashore in under 90 minutes. The National Seashore itself is the crown jewel, a 43,000-acre protected landscape of beaches, dunes, forests, and freshwater ponds that stretches from Chatham to Provincetown. Nauset Light Beach and Coast Guard Beach are consistently ranked among the best in the country.
Provincetown, at the very tip of the Cape, is a destination unto itself. The Provincetown Art Association and Museum is excellent, as are the galleries, restaurants, and street performers along Commercial Street, which is unlike anything else in New England. Whether you come for the beaches, the history, or the lobster rolls, Cape Cod delivers every time.
Rockport
An hour north of Boston, Rockport sits at the tip of Cape Ann. This compact village of art galleries, lobster shacks, and centuries-old granite buildings is perched at the edge of the sea and is a popular New England destination. The town's most photographed subject is Motif Number 1, a weathered red fishing shack at the end of Bradley Wharf that has been painted and sketched by so many artists over the years it's said to be the most painted building in America.
The entire harbor area is equally lovely, with lobster traps stacked on the docks, fishing boats in the cove, and the rocky shoreline stretching out in both directions endlessly. Bearskin Neck is the heart of Rockport, housing galleries, craft shops, and restaurants. Browse for handmade jewelry and ceramics or watch local artists at work in open studios. For lunch, a cup of chowder or a plate of steamed clams at one of the dockside spots is mandatory.
Salem
Just 25 miles north of Boston, Salem is one of those places that manages to be both a serious historical site and a fun-filled destination at the same time. Most people know it for the Salem witch trials, and that dark chapter is indeed central to the Salem experience, but there's so much more to explore than the town's macabre history. Start at the Peabody Essex Museum, one of the finest art and culture museums in New England. Founded in 1799, it houses an extraordinary collection of maritime art, Asian art, and artifacts from Salem's days as one of the wealthiest ports in the United States.
From there, walk the Heritage Trail that guides you through Salem's most significant historic sites. You'll pass the Witch Trials Memorial, a moving tribute to the twenty people executed in 1692. Nearby is the Charter Street Cemetery, one of the oldest in the country. Finally, the Salem Witch Museum offers an immersive presentation of the trials and is suitable for all ages. Salem's Pickering Wharf is perfect for lunch, with waterfront restaurants serving New England classics, like chowder and lobster rolls. The best time to make this trip is in October, when the whole city leans into its spooky reputation with elaborate decorations, street performers, and plenty of tricks (and treats!)
Mount Greylock Scenic Byway
Drive west from Boston for about 2.5 hours, and the state transforms completely. At 3,491 feet, Mount Greylock is the highest point in Massachusetts and one of the most scenic drives in the entire region. The Mount Greylock Scenic Byway begins in Lanesborough and winds upward through state reservation land to the summit, where the Veterans War Memorial Tower rises 92 feet above the mountaintop. On a clear day, the tower's observation deck offers views into Massachusetts, Vermont, New York, Connecticut, and New Hampshire. Day hikers can even tackle sections of the Appalachian Trail, which crosses the summit, or venture down through the forest on trails that pass mountain streams and old-growth northern hardwoods. Below the mountain, the Berkshire valley towns of Adams and Williamstown offer additional attractions. Massachusetts Museum of Contemporary Art in North Adams is one of the largest contemporary art museums in the world, occupying a converted 19th-century factory complex that is itself a work of art.
Newport
Cross the state line into Rhode Island and follow the coast south for about 90 minutes from Boston, and you'll arrive in Newport. Few day trips from Boston deliver such a dramatic change of scenery in such a short drive. The Cliff Walk is the quintessential Newport experience, a 3.5-mile path that hugs the edge of Aquidneck Island's eastern shore, with the Atlantic crashing on the rocks below and the Gilded Age mansions of Bellevue Avenue rising just above the path.
The sprawling estates were built by the economic titans of the late 19th century as summer cottages. The Breakers, the Vanderbilt family's 70-room Italian Renaissance-style palazzo, is the crown jewel and is worth a guided tour. Beyond the mansions, Thames Street's waterfront is lined with restaurants, sailing shops, and boutiques. Newport's culinary scene is excellent and features fresh seafood, naturally, but also boasts an increasingly sophisticated dining culture that matches the city's cosmopolitan character.
Plymouth
Less than an hour south of Boston on Route 3, Plymouth is America's first hometown where pilgrims aboard the Mayflower stepped ashore in 1620 and began the process of building what would eventually become the United States of America. It's a destination that could easily feel like a stuffy history lesson, but Plymouth does an exceptional job of bringing its story to life in a way that's engaging for all visitors. Plymouth Rock, the famous boulder on the waterfront that marks the traditional landing site of the Mayflower, is smaller than most people expect, but it's interesting nonetheless. The full-scale reproduction of the Mayflower, Mayflower II, is docked nearby and offers a sense of just how audacious the original crossing truly was.
Plimoth Patuxet Museums is the highlight of this day trip. This living history museum features a fully reconstructed 17th-century Wampanoag homesite and a Pilgrim village, with interpreters in period and traditional clothing who speak, work, and live as their historical counterparts did. Plymouth's downtown is also genuinely pleasant, with a waterfront park, good seafood restaurants, and a lively year-round farmers' market.
Old King's Highway
Stretching along Cape Cod's north shore, Old King's Highway, officially Route 6A, is one of the oldest roads in America and an official National Scenic Byway. What makes this route perfect for a day trip is not just the scenery, but the number of things to discover along the way. The drive begins in Sandwich, an hour south of Boston and the Cape's oldest town, where you can visit the Sandwich Glass Museum and discover hand-blown pieces that put this village on the map. From there, the route winds through the coastal towns of Barnstable, Yarmouth, and Dennis, each with white-steepled churches, antique shops, and plenty of Instagram-worthy photo ops. The Cape Cod Bay side of the peninsula is quiet and relaxing, ideal for kayaking or a walk along the shore.
Douglas State Forest
An hour southwest of Boston near the Rhode Island border, Douglas State Forest covers nearly 6,000 acres. It's one of the largest state forests in Massachusetts, and it offers a diverse experience in nature for a day trip that most visitors to the region overlook. The forest is threaded with miles of multi-use trails ranging from easy lakeside walks to rugged backcountry routes. The main attraction for many visitors is Wallum Lake, with clear waters and a beautiful sandy beach. On a warm summer day, it's a perfect spot for swimming, without the crowds you'll find on the Cape or the Vineyard. The Coffeehouse Loop is a favorite among hikers. This moderate circuit takes you through varied terrain, including raised boardwalks, boggy lowlands, and sun-dappled mixed hardwood forest. For a day trip that feels genuinely off the beaten path, Douglas State Forest is hard to beat.
Happy Travels
Within a radius of only two or more hours from Boston, you can stand on a mountain summit gazing into five states, walk the cobblestones of America's most historically rich towns, hit the beach, or pedal past wild roses on an island where time moves to its own rhythm. These 10 amazing Massachusetts destinations for a day trip represent some of the region's very best. The coastline, the forests, the hills, and the history are all there, waiting patiently for curious travellers willing to venture a little beyond the city.
