During all four seasons of the year, Massachusetts is home to some wonderfully scenic hiking trails. Whether you’re a seasoned hiker—or going just a few paces above a leisurely stroll—you’ll experience nature at its best during any season on the following trails. In addition to the scenery and the benefit of some rigorous outdoor exercise, several of these trails are of historical significance, too.
Beginning as far north as Newburyport’s Plum Island, the Parker River National Wildlife Refuge was established as a feeding and nesting ground in Massachusetts for migratory birds. Comprised of more than 4,700 acres, including salt marsh, freshwater marsh, sand beach, cranberry bog, maritime forest and more, the refuge is home to more than 300 migratory bird species. In the midst of this productive ecosystem are hiking trails that allow outdoor enthusiasts to take it all in. In addition, visitors can tour the grounds via bicycle and kayak. Depending on how much snow covers the ground in winter, the trails may or may not be open. Hikers are welcome in spring, summer, and fall. Hikers of all skill levels will enjoy these trails.
The Appalachian National Scenic Trail spans from Georgia to Maine, featuring hikes in those states and every one in between. In Massachusetts, hikers take to the trail in North Adams. A visit in October affords hikers a taste of Massachusetts in its peak of finery during the Fall Foliage Festival. Not recommended for novice hikers, it’s best to have at least a bit of experience before hitting the trail.
An easy 3.5 miles of hiking trails grace The Doyle Estate in Leominster. An urban oasis that is open year round, the trails are part of a former family estate and include parklands, a formal garden, woodlands, meadows, and open fields. Gorgeous any time of year, it’s the perfect place for novice hikers to build up their stamina for more skilled hikes.
Part of the Lincoln Land Conservation Trust, Mount Misery in Lincoln features marked hiking trails that are also opened to cross country skiers and horseback riders. Bicyclists may use trails that are clearly marked for them alone. Open from dawn to dusk year round, there is ample designated parking for hikers. The trails are perfect for those with novice to intermediate skills.
Twelve easy hiking trails, which are all open year round, comprise the Cape Cod National Seashore. The Fort Hill, Buttonbush, Red Maple Swamp, Nauset Marsh, and Doane trails are in Eastham. The Atlantic White Cedar Swamp and Great Island Trails are in Wellfleet, and the Beech Forest Trail is located in Provincetown. Visit the website and print a trail guide for each one. In addition to these beautiful trails, the Cape Cod National Seashore’s many miles of pristine beaches are a favorite among hikers.
Located just outside of Boston, in Milton, the Blue Hills Reservation features hiking trails in both an upper and lower forest, along marsh, swamp and pond edges, and in both meadows and a white cedar bog. Perfect for hikers of all skills, the reservation is rich in both archaeological and historical significance. One of the first areas purchased and set aside for recreation in the Boston region, Native Americans once graced the land. It was later farmed by Massachusetts farmers. Quarry workers worked the land there, too.
Dover’s Noanet Woodlands features 17 miles of hiking trails. A hike to the top of Noanet Peak affords hikers some amazing views of the Boston skyline. An easy half mile hike on Caryl Trail is perfect for children. The Peak is recommended for more experienced hikers. In addition to hiking, the trails are available for cross country skiing and snowshoeing in the winter, and for birding all year round.
Featuring 503 acres of open space, Monument Mountain is the name given a reservation in Great Barrington. Located in the southern Berkshires, hikers have been drawn to the area for more than 200 years. At the 1,642-foot summit of Squaw Peak, those who have successfully ascended the trail will be treated to views from the New York Catskills to southern Vermont. Monument Mountain isn’t for the faint of heart. While there are circular trails for less accomplished hikers, only those with some experience should climb to the top.
Featuring 70 miles of hiking trails—11.5 of which intersect with the Appalachian Trail—Mount Greylock State Reservation in Lanesborough features the highest spot in the state of Massachusetts at 3,491 feet. Weather permitting, the roads to the trails are open from May through the end of October. The first wilderness state park in the state, it was purchased by Massachusetts back in 1898. The website provides a printable trail map for hikers.
Situated on 2,200 acres spanning Medford, Malden, Melrose, Winchester, and Stoneham, Middlesex Fells Reservation is a state park with easy hiking trails—many surrounding Bellevue Pond. Featuring 100 miles of trails, hikers can ascend from the pond up to Wright’s Tower, where they can take in gorgeous views of Boston Basin. Comprised of the Skyline Trail, Reservoir Trail, The Rock Circuit Trail, Crystal Springs Trail, and the Cross Fells Trail—the reservation is open to hikers from May through the end of October.
If history and hiking are fighting for first place in your list of interests, you’ll enjoy the Minute Man National Historic Park in Concord. An easy hike to the North Bridge in this scenic park brings you to the place the first Revolutionary War battle took place. Close your eyes upon arrival and imagine the sound and smell of musket fire.
Ward Reservation in Andover features three sizable hills—all connected with hiking trails. Shrub Hill, Boston Hill, and Holt Hill offer hikers beginner to advanced beginner trails. Solstice stones on Holt Hill mark the highest spot in all of Essex County. The views from tops of all three hills are spectacular.
Offering hikers 12 miles of hiking trails, comprised of meadows, forests, esker, drumlin and wetlands, Mass Audubon’s Ipswich River Wildlife Sanctuary in Topsfield is also a birder’s paradise. Special events—including a Halloween Trail in October—take place until winter. Diehard outdoor enthusiasts wanting even more exercise and adventure can take a canoe down the river following their hike.
Great Brook Farm State Park, located in Carlisle, features a moderate hike along The Acorn Trail. A narrow, winding trail, hikers follow it through woods and a field, and up a small hill. The state park features an ice cream stand that stays open until mid-October, for those wanting to treat themselves after their hike. The ice cream is sourced from the Holsteins that have been present on the property for about 60 years. Prior to that, Native Americans used the land for some of their sacred rituals.
When hiking Race Brook Falls in Sheffield, hikers can visit two summits—Mount Everett and Mount Race. Mount Everett is the highest peak in the southern part of the Berkshires. Just over the border from Connecticut, the trails are popular with hikers in the tri-state—Massachusetts, Connecticut, and New York—area.
Once you’ve hiked these 15 best hiking trails in Massachusetts, you’ll not only be a rather accomplished hiker, you’ll also know a lot more about the Commonwealth. Keep this list handy so you can eventually check each of them all off yours.