Best cross country skiing trails in Massachusetts

13,649 Reviews
Explore the most popular cross country skiing trails in Massachusetts with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.
Map of cross country skiing trails in Massachusetts
Top trails (114)
#1 - Hickey and Peeskawso Peak Trail
Monument Mountain Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(623)
Length: 2.8 mi • Est. 1 h 35 m
Note: The term squaw is considered universally offensive by Indigenous groups in America due to its use for hundreds of years in a derogatory context. Indigenous activists have continued to work both locally and in more general educational efforts, to rename the locations across North America that contain the slur, as well as to eliminate the slur from the lexicon in general. See here for more info: https://en.wikipedia.org/wiki/Squaw#Efforts_to_rename_placenames_and_terms_with_squaw_in_themShow more
#2 - Borderland State Park Loop Trail
Borderland State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(721)
Length: 8.5 mi • Est. 3 h 43 m
$5 parking fee unless you have an annual pass. As of April 2020, there are a few trails on the northern park boundary that are closed to hikers.Show more
#3 - World's End Trail
Boston Harbor Islands National Recreation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(545)
Length: 3.8 mi • Est. 1 h 43 m
Rolling hills and rocky shorelines offer sweeping views of the Boston skyline, while tree-lined carriage paths designed by famed landscape architect Frederick Law Olmsted make delightful walking trails. $8 per person for non members/$6 for members/Children get in free.Show more
#4 - F. Gilbert Hills State Forest Loop Trail
F. Gilbert Hills State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(721)
Length: 7.1 mi • Est. 3 h 17 m
Off-road motorcycle driving is allowed May - November ONLY on the "Mountain Bike/Motorcycle Trail". 4WD trucks are not allowed.Show more
#5 - Weir Hill Reservation Trail
Weir Hill Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(553)
Length: 2.6 mi • Est. 1 h 12 m
Please see the Weir Hill park page for up to date information: http://www.thetrustees.org/places-to-visit/northeast/weir-hill.html The map shown has the hiker starting at Stevens Pond. There is another entrance about a half mile north on Stevens Street. This route is marked with yellow blazes.Show more
#6 - Massasoit Trails
Massasoit State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(462)
Length: 7.9 mi • Est. 3 h 10 m
As of February 2020, dam is out so you may have to find an alternative route.Show more
#7 - Gates Pond
Brewer Brook Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(349)
Length: 2.4 mi • Est. 1 h 2 m
#8 - Douglas Forest Wallis Pond Loop Trail
Douglas State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(335)
Length: 5.6 mi • Est. 2 h 27 m
#9 - Vetter Trail and Ward Trail Loop
Ward Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(344)
Length: 3.6 mi • Est. 1 h 42 m
Note: As of November 2020, users have reported the top of the trail closed for restoration. There is a $5 parking fee.Show more
#10 - Pine Hill, Harrington, Jack Frost, Bicentennial, and Mountain House Trail Loop
Wachusett Mountain State Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(216)
Length: 2.8 mi • Est. 1 h 54 m
Parking fee: MA resident $5 Non-MA resident $20 Rising above the surrounding forest to a height of 2006 feet, Mount Wachusett stands as a unique landmark within the central New England landscape. From the summit, a clear day reveals views of Mt. Monadnock in New Hampshire, the Berkshires to the west, and the Boston skyline to the east. The 3,000-acre Wachusett Mountain State Reservation surrounds the summit and offers a wealth of natural and recreational resources. The Reservation's natural resources include forests, alpine meadows, ponds, streams, fields, and even a perched bog. Recreational opportunities abound at the reservation including hiking, nature study, hawk watching, picnicking, and skiing. The Reservation offers 17 miles of hiking and walking trails.Show more
Showing results 1 - 10 of 114