Find Waterfalls and Castles at the Most Beautiful Places in Massachusetts

From Boston to Martha’s Vineyard, these are the most stunning spots in the state.

Beautiful Places to Go in MA
Hammond Castle on the coast of Gloucester, Massachusetts | Evgeshag/Getty Images
Hammond Castle on the coast of Gloucester, Massachusetts | Evgeshag/Getty Images

New England is home to some of the most alluring attractions, scenic overlooks, and notable landmarks you can find. And while Boston might be at the top of Massachusetts’ places to visit, there are plenty of places outside the city worth exploring. From a century-old castle nestled into rocky cliffs to a waterfall that cascades 80 feet into an emerald pool, the state holds more than enough destinations to add to your itinerary.

To help narrow down some of Massachusetts’ most desirable spots, we’ve rounded up the most beautiful places around that are worth visiting—from the famous to the lesser known. And for even year-round fun, check out the Best Places for Skiing and the Best Places for Fall Foliage.

Boston Harbor Hotel | Photo credit: Aimintang, via Getty Images

Beautiful Places in Boston and Greater Boston

Located at the edge of the Financial District, this iconic hotel is difficult to miss, with a 60-foot stone archway looking out into the Boston Harbor (hence the name). It’s no wonder this place is a hotspot for engagement and wedding photos. While the hotel’s interior lives up to its five-star reputation, it’s the exterior that adds to the beauty of it all. Its adjacent marina makes for memorable strolls and captures some of the city’s best sights. Not to mention the hotel overlooks The Rose Kennedy Greenway and is along the way to the sought-after neighborhood of Seaport.

Spend an afternoon traipsing through DeCordova’s 30-acre sculpture park, the largest such destination in New England. For the full experience, plan for two hours to explore the 60 large-scale installations. Leashed pups are also welcome, just be sure to book your visit to the grounds and museum ahead of time as it’s strongly encouraged.

Beautiful Places to Go in MA
Hammond Castle | Photo credit: Pmstephens, via Getty Images

Beautiful Places in North Shore

Opening back up in April, this historic landmark and dynamic STEM museum located along Gloucester’s rocky coast was built over a century ago by the “Father of Radio Control,” John Hays Hammond. The castle was originally Hammond’s residence and lab, where he housed a collection of artifacts from ancient Rome through the Renaissance (casual). Today, visitors can explore the many rooms of the medieval castle and magical grounds that overlook the ocean.

A New England favorite, Singing Beach is known for its fine white sand and the certain sound (some say it’s 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 15 to April 15, 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 Lights Historic District, which is some of the oldest lighthouses in the country.

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 to learn about the estate’s history and witness panoramic views of the ocean atop Castle Hill. Fun fact, the castle makes an appearance in movies like Ghosts of Girlfriend’s Past, The Equalizer and Little Women (2019 version).

Beautiful Places to Go in MA
Bash Bish Falls | Photo credit: Lightphoto, via Getty Images

Beautiful Places in Central Massachusetts and Western Massachusetts

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 and botanical mixology classes to gardening workshops, Tower Hill is chock-full of activities set amongst some of nature’s most vibrant and beautiful blooms.

Mount Washington
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.

Through Lee, Becket, Chester, Huntington, and Russell
Embark on a picturesque drive throughout the Berkshires and 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. Speaking of pit stops, there are a few noteworthy attractions along the route, including the Keystone Arch Bridges, a series of stone arch bridges built in 1840 that trainspotters are sure to appreciate, and from June 26 to August 25, check out the country’s longest-running international dance festival, Jacob’s Pillow Dance Festival.

Lanesborough, North Adams, Williamstown
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 in mid-May). The good news? The reservation offers plenty of year-round hikes, both easy and invigorating, that offer stunning nature sites and views.

A historic and rugged landscape created by geologic upheavals 500 million years ago, in the summer, Bartholomew’s Cobble offers five miles of hiking trails boasting grassy meadows, shady forests, and freshwater marshes. For added adventure, head to Hurlburt’s Hill, the highest point on the property, for panoramic views of the Housatonic River Valley. But most definitely plan a trip this April to early May, when the wildflowers are in full bloom.

Beautiful Places to Go in MA
Aquinnah Cliffs Overlook | Danita Delimont/Flickr

Beautiful Places in the Cape and Islands

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.

Martha's Vineyard
Set in Martha’s Vineyard, you’ll find the spectacular Aquinnah Cliffs on the southwestern tip of the island. The colorful clay cliffs, which are said to be carved by glaciers millions of years ago, look out to the ocean and feature paths that lead to attractions like the over two century-year old Gay Head Lighthouse. And located just below the light, there’s Moshup Beach, which is not your average beach: It happens to be one of the world’s best nude beaches.

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. Menemsha Hills is open year-round and guarantees stunning views throughout the seasons.

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Jillian Hammell is a contributor for Thrillist. Follow her on Instagram.
Meaghan Agnew is a contributor for Thrillist. Follow her on Instagram.