Plan Your Path to a Perfect Stay in Massachusetts
Whether by foot, bike, or boat, put yourself on the trail to outdoor adventure in the Commonwealth.
By Yankee Custom Editors|Jan 05 2026|
Monument Mountain, Great Barrington, MA
Photo Credit: Dan/stock.adobe.comSponsored by the Massachusetts Office of Travel and Tourism
The Massachusetts landscape is surprisingly varied: Rugged mountains, winding rivers, and breezy coastlines all offer welcome diversity in outdoor enjoyment. Hoping for a heart-pumping hike? Take your pick. More in the mood for a gentle walk by the ocean? There are plenty of those, too. If you’d rather pedal, paddle, or ski, the state is teeming with even more options to strike your fancy. The only problem won’t be finding a place to hit the trails, but deciding which one to enjoy.
Hiking Trails
A long drive isn’t necessary to get the elevation gain you’re after. You can climb a whopping 1,832 feet right in Ashburnham. At the southern end of the Wapack Range, Mount Watatic rewards you with views of the Green Mountains in Vermont and the peaks of southern New Hampshire. In Holyoke, there’s Mount Tom, a fairly steep hike with a high likelihood of migrating hawk sightings. At the top, the rolling hills of the Pioneer Valley unfold before you.
Boston hikers are loyal to their beloved Blue Hills Reservation. There, the Skyline Trail leads to the top of Great Blue Hill; the 3.5-mile trek requires some climbing to reach the summit. Once you do, you can opt for another climb up Eliot Tower, which frames views of the city skyline. Head to the Berkshires for a challenging journey all the way up Monument Mountain; prepare to get a bird’s-eye view of the Housatonic River Valley.
Photo Credit : Nancy Kennedy/iStock
Coastal Trails
If a stroll through salt air is more your speed, the Bay State has many trails that live up to its nickname. Bird watchers will delight in the paths crisscrossing Parker River National Wildlife Refuge in Newbury. You’ll spend most of your visit on Plum Island, with the ocean on one side of you and salt marshes on the other. World’s End highlights a similarly immersive experience as you trace four drumlins jutting out into Hingham Bay, seemingly surrounded by deep-blue waters.
Along the hook-shaped arm of Cape Cod, the Great Island Trail in Wellfleet puts Massachusetts’s coastal beauty on dazzling display. You have the option to complete an almost-9-mile loop along the beach and through pitch pine forests, punctuated by plenty of scenic overlooks. The iconic scenery continues at Mattapoisett’s Nasketucket Bay State Reservation, where you’ll get a front-row seat to eelgrass meadows, coastal forests, salt marshes, and shellfish beds during your tranquil walk.
Photo Credit : J. DeLorenzo/courtesy of The Trustees
Paddling Trails
The only thing better than a leisurely paddle down the river is a paddle with a history lesson mixed in. If you bring your kayak or canoe to the Blackstone River in Millville, you can stop by the Millville Lock, one of the best-preserved locks from the former Blackstone Canal. There’s also a visitor center in nearby Worcester spotlighting the area’s heritage. The Ipswich River, meanwhile, flows 45 miles from Burlington to Ipswich. Paddling here is mostly flat and relatively free from development.
That’s not the case for the Charles River, where you can put your boat in the water at the DCR’s public launch along Nonantum Road in Brighton. Paddle toward Boston to see the boathouses for numerous colleges and universities, or head inland to follow joggers along the Charles River Greenway. In Royalston, the Tully River offers another compelling kayaking experience, passing verdant wetlands on the way to Tully Lake, where there are isles and inlets to explore.
Photo Credit : Massachusetts Office of Travel and Tourism
Rail Trails
The Commonwealth’s bevy of bygone railroads has resulted in lots of opportunities for biking—in the form of rail trails, that is. And with the DCR’s Universal Access Program, cyclists of all abilities can join in, thanks to staff-supported adaptive cycling programs. Consider taking a ride down the Bruce Freeman Rail Trail, which stretches 20 miles from Lowell to Sudbury along the old New Haven Railroad. There’s also the Cochituate Rail Trail nearby, connecting Framingham to Natick via a paved, leafy path.
Some of the state’s best biking can be enjoyed on the Cape Cod Rail Trail, which winds through salt marshes, inlets, beaches, and forests from Yarmouth to Wellfleet. There are also several bike rental opportunities along the trail, like Barb’s Bike Shop in South Dennis and Orleans Cycle in Orleans. In Western Mass., the Ashuwillticook Rail Trail links Pittsfield to Adams, passing the Cheshire Reservoir and Hoosic River along the old Pittsfield and North Adams Railroad.
Photo Credit : Courtesy of Wachusett Mountain Ski Area
Ski Trails
Winter may be prime time for skiing in Massachusetts, but spring skiing shouldn’t be overlooked, as nearly a dozen mountains are open until mid-to-late March. Start making plans to glide down the slopes at Berkshire East Mountain Resort in Charlemont, the world’s first ski area powered entirely by on-site renewable energy, or carve up dozens of trails at Wachusett Mountain Ski Area, complete with a base lodge with lots of restaurants, plus a hot-cider house and a waffle cabin.
For more Massachusetts travel inspiration, go to: visitma.com
