An Insider’s Guide to Massachusetts: 4 Hidden Treasures in the Bay State

While many of us have come to call Massachusetts a second home, nobody knows the ins and outs like the locals. From scenic overlooks in the beautiful Berkshires to lesser-known ports-of-call, spice up your next getaway by soaking in these sights off the beaten path (shared with us by native Bay Staters themselves).

An Insider’s Guide: 4 Lesser-Known Things To Do in Massachusetts

1. The Observation Tower at Quabbin Reservoir (Ware, MA)

Folks in western Mass consider themselves lucky to have pristine mountain and water views right in their backyards (sometimes literally). A locally-loved way to set your sights on both at once is with a trip to the Quabbin Reservoir and its 181 miles of coastline. An 84’ tower at the summit of the Great Quabbin Hill offers an unbeatable view of this Bay State great. Access the tower by driving up Quabbin Hill Road (a little less than an hour outside Worcester), or let it be the cherry on top of your nature hike along the Quabbin Hill Trail.

Insider submission from Catherine H.

2. Keystone Arches Trail (Middlefield, MA)

While you’re in the area, don’t skip a trip to the Keystone Arches Trail in Middlefield. As its name implies, this route passes several historic, beautiful arched bridges of stone, including a colossal 70-foot structure — the largest ever built along the rail trail in the 1840s. They now rest undisturbed, covered in vining plants and trees as eye-candy rewards for those willing to conquer the trail.

The Keystone Trail is also an ideal destination for serious outdoor enthusiasts. Some parts of the off-road trail stay wet throughout the summer, adding an extra challenge of mud and water for moderate and expert mountain bikers. It’s also home to the only uncontrolled branch of the Westfield River. With class IV rapids that see 50-foot drops, expert kayakers can head here for some thrills that’ll be tough to top.

Insider submission from Virginia R.

3. The Bridge of Flowers (Shelburne Falls, MA)

Weighing the merits of a romantic getaway to Massachusetts? Leave it to the Bridge of Flowers in Shelburne Falls to seal the deal. Although Beantown tends to steal the spotlight, western Mass is proud of this aromatic attraction. It’s one of the most swoon-worthy sights you’ll see in Massachusetts: a bridge blanketed in beautiful blooms and backdropped by picturesque mountain views. If you’ve got a green thumb of your own, see what’s coming and time your trip with the species of flora you’d most like to feast your eyes on.

Insider submission from Sharon H.

4. West Island (Fairhaven, MA)

Perhaps you’ve cruised out to Martha’s Vineyard or Nantucket once or twice, but have you ever set foot on the shores of West Island in Fairhaven? At just 535 acres, this small island nestled between Buzzards and Nashetucket Bays can fit inside Central Park in New York City, but don’t let its size fool you. Leave the crowds on the big-name islands and make waves with your favorite coastal pastimes, from kayaking to jet skiing to simply sunbathing on the serene shores of West Island Beach. You don’t have to wait until summertime to complete your island tour, either — the beach and walking trails up to North Point stay open and ready to explore year-round.

Insider submission from Susan D.

Before you start planning your tour of these somewhat-secret nooks and crannies in Massachusetts, be sure to make a reservation at one of our Massachusetts inns or resorts — not to brag, but we happen to know a thing or two about the Bay State ourselves.