The Most Beautiful Places to Visit in Massachusetts
From waterfalls in Western Massachusetts to sprawling sandy beaches on the coast, these are the most beautiful places in the state worth a day trip.
New England is simply where it’s at when it comes to jaw-dropping sights. There's plenty of cool things to see and do in Boston, of course. But beyond the Freedom Trail and historic buildings, there are dozens of picturesque places just outside the city in Massachusetts that call for a documented day trip regardless of the season.
To help narrow down some of the state’s most desirable and historic spots, we’ve rounded up the most beautiful destinations around that are worth visiting for a quick hike, day of exploring, or full weekend getaway.
A New England favorite, Singing Beach is known for its fine white sand and the certain sound (some say it sounds like more of a squeak) because of the sand’s unique size, shape, and makeup. Aside from its “singing,” the beach makes for a tranquil stop not only during summer but also in the winter and spring months. Plus, from October to mid-April, dogs are permitted to frolic along its shores.
The seaside town of Rockport is already a must-visit, but if you’re looking for established trails, Halibut Point State Park is your spot. Between rocky ledges and views that go on for miles (quite literally as you can see Maine’s Mount Agamenticus off in the distance), the state park makes for an unforgettable stroll. While you’re in town, make sure you visit the local shops and art galleries, and while you’re at it, don’t forget to check out the Twin Lighthouses, among some of the oldest lighthouses in the country.
What better place to hit up in the springtime than a beloved Massachusetts botanical garden? The Tower Hill Botanic Garden, which includes 17 distinct gardens across 171 acres, is home to a prized collection of seasonal plants, shrubs, trees, and more. From yoga classes to guided walks, Tower Hill is chock-full of activities set amongst some of nature’s most vibrant and beautiful blooms.
In 1910, Chicago industrialist Richard T. Crane, Jr. purchased what would later become The Crane Estate featuring his summer home—an over 56,000 square foot Tudor Revival mansion sitting on the national historic landmark, Castle Hill. The family mansion, along with its famous grounds, are available for guided tours, hikes, and more adventures, where you’re able to learn more about the estate’s history and witness panoramic views of the ocean atop Castle Hill.
Forget what you know about swamps and venture off to Wellfleet to stroll down a winding boardwalk and onto the historic Old Wireless Road (made of sand) at White Cedar Swamp. The mile-long loop takes you into covered woodlands, and if you’re up for the adventure, visit the east side of Marconi Station Site (located at 99 Marconi Site Road) for a cliffside ocean view.
Set in Martha’s Vineyard, you’ll find Aquinnah Cliffs (formerly Gay Head) on the soutwestern tip of the island. The colorful clay cliffs look out to the ocean, and if you’re lucky, you might get a front row seat to some quality whale watching. Just a heads up, you might also get a few unexpected sights as when summer hits, the remote section of Moshup Beach, directly beneath the cliffs, is also known as an unofficial nude beach.
The state’s highest waterfall, Bash Bish Falls, is a popular and surprisingly doable hiking destination for local and visiting outdoor enthusiasts. The 80-foot drop, which plummets into a deep, crystal-clear pool below, is a sight worth seeing but keep in mind that swimming is prohibited.
Spend an afternoon traipsing through DeCordova’s 30-acre sculpture park, the largest such park in New England. For the full experience, allow yourself two hours to explore the 60 large-scale installations and you can even bring your leashed pup to make an afternoon of it. Plus The Twisted Tree Cafe is now open, serving up breakfast, lunch, coffee, pastries, and more. Just be sure to book your visit to the grounds and museum ahead of time.
As the highest point in Massachusetts, Mount Greylock sits at 3,491 feet, providing views as far as 90 miles away. Here’s the bad news: the summit driving routes are closed in the deep winter (opening back up May 21). The good news? The reservation offers plenty of year-round hikes, both easy and invigorating, that offer stunning nature sites and views.
Surrounded by rocky edges and the ocean, venture off to Menemsha Hills to enjoy one of the longest walks on the Vineyard. Make sure to stop at the top of Prospect Hill, the second highest point on the Vineyard, for exceptional sights of the Elizabeth Islands. The reservation is open year round.
A historic and rugged landscape created by geologic upheavals 500 million years ago, in the summer Bartholomew’s Cobble boasts grassy meadows, shady forests, and freshwater marshes, but its five miles of hiking trails are beautiful year-round. For added adventure, head to Hurlburt’s Hill for panoramic views of the Housatonic River Valley. And plan on returning in mid-April to early May, when the wildflowers are in full bloom.
Through Lee, Becket, Chester, Huntington, and Russell
If you’re looking to embark on a picturesque drive throughout the Berkshires, set your GPS to Jacob’s Ladder Scenic Byway. The route features top-notch scenic overlooks and winds its way through quaint towns worth taking a pit stop for some fresh air.