Spend a Day Hiking, Picnicking, and Stargazing on a Central Massachusetts Day Trip

Looking for new adventures close to home? Venturing beyond 128 has its rewards—namely, mountain-climbing, stargazing, and one very satisfying chili dog. Along the way, you'll discover remnants of old mill towns that bring the state's manufacturing history to life. For more local hikes, try reading 50 Hikes in Eastern Massachusetts.

Blackstone River Greenway / Photo by Milo Bateman/Rail to Trails Conservancy

Approximate Drive Time From Boston: 50 minutes


Crow Hills, Westminster

This stunning hike in Leominster State Forest feels worlds away, yet is only a quick drive up Route 2. Park in the lot on Fitchburg Road in Princeton, then cross the street to climb a series of stone steps and ledges. You’ll notch 275 feet in elevation in just a few minutes, and from the top, you can glimpse Crow Hill Pond and nearby Mount Wachusett.

Mount Watatic, Ashburnham

Ditch the crowds scaling the ever-popular Mount Wachusett in favor of this monadnock near the New Hampshire border, one of the highest peaks in the state east of the Connecticut River. On a clear day, you can spy Vermont’s Green Mountains and the peaks of southern New Hampshire from the summit.

Purgatory Chasm state reservation, Sutton

Steep drop-offs and scenic passageways invite thrill-seekers to this rocky fissure off Route 146. Climbing up and through the unique rock formation is an exhilarating agility test, but if wedging your way through skinny crevices like “Fat Man’s Misery” isn’t up your alley, the low-key, 1.5-mile Chasm Loop Trail circles the gorge without forcing you to hoist yourself onto any rock faces.

Assabet River Rail Trail / Photo courtesy of Wikipedia


Assabet River Rail Trail, Marlborough to Hudson

Wind through old mill towns along this rail trail, which runs on an abandoned branch of the Fitchburg Railroad. For the perfect afternoon sojourn, hop on in Marlborough by parking near Kelleher Field and ride 5.8 miles to newly hip Hudson, passing brooks and reservoirs and 19th-century mill buildings. Your sweet prize? A scoop of vanilla-bourbon ice cream from New City Microcreamery.

Mass Central Rail Trail, Rutland to Barre

Local advocacy groups are working to transform a former railroad route that once spanned from Boston to Northampton into a continuous 104-mile bike path. Until then, the best place to get on is the section completed by the nonprofit group Wachusett Greenways, where you can pedal past forested conservation areas and wetlands along a rocky cliff.

Blackstone River Greenway, Uxbridge to Blackstone

Cross eight bridges showcasing panoramas of the historical Blackstone River along this 3.5-mile portion of the Blackstone River Greenway, which will eventually connect Worcester to Providence. Be sure to hop off your bike for a quick walk to the Millville Lock, the only intact lock out of 48 that once allowed canal boats to pass through it.


Worcester may be Massachusetts’ newest dining mecca, but nothing beats the comfort of 102-year-old George’s Coney Island, which doles out hot dogs for about $3 apiece. Make like a local and order one with the works (yellow mustard, chili sauce, and chopped onion) and a Polar Orange Dry.


Picnic Under The Stars

Part of the Last Green Valley National Heritage Corridor, south-central Massachusetts is one of the few remaining swaths of uninterrupted green space from Boston to Washington, DC. Not surprisingly, the huge stretch of rural land offers a rare dark sky ideal for stargazing—try it at Sturbridge Trails Heins Farm Conservation Area, where you can park for free and relax in a field shielded from headlights.


Plan ahead and reserve a time to visit the Massachusetts Horticultural Society’s Gardens at Elm Bank, a combination of historical and contemporary flower gardens in Wellesley. Kids in tow? Curbside pickup of something sweet from Hebert’s Candy Mansion in Shrewsbury should keep energy levels high. And if you have the energy for it after a day on the trails, round out a classic New England summer day with a nighttime showing at the Mendon Twin Drive-In before heading back to Boston.

More Day Trip Ideas to Escape the City