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Best Trail Running in Massachusetts

This list represents the most popular trail running in Massachusetts. Use this list to plan your next Massachusetts trail running trip. Select a state and/or activity below to find even more top trails.

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#1 Bash Bish Trail
Bash Bish Falls State Park, MA
7
Bash Bish Trail is a hiking trail in Mount Washington, Massachusetts. It is within Bashbish ...
#2 Alander Mountain Trail
Mount Washington, MA
9
Alander Mountain Trail is a hiking trail in Mount Washington, Massachusetts. It is 2.6 ...
#3 Race Brook Trail
Berkshire County, MA
7
Race Brook Trail is a hiking trail in Berkshire County, Massachusetts. It is 1.8 miles ...
#4 Monument Mountain
Great Barrington, MA
4
For almost two centuries, Monument Mountain has been a source of inspiration for many ...
#5 Bald Hill Road
J. C. Phillips Sanctuary, MA
5
Bald Hill Road is a hiking, biking, and horse trail in Boxford, Massachusetts. It is within ...
#6 Ice Glen Trail
Stockbridge, MA
3
Ice Glen Trail is a hiking trail in Stockbridge, Massachusetts. It is 0.5 miles long and ...
#7 Tully Mountain (gradual Ascent)
Tully Mountain WMA, MA
2
Tully Mountain (gradual Ascent) is a hiking trail in Orange, Massachusetts. It is within ...
#8 Rocky Woods Reservation
Medfield, MA
0
This loop tours three small lakes in a loop from Chickering Pond to Notch Pond to Echo ...
#9 Harold Parker Road
Essex County, MA
4
Harold Parker Road is a hiking, biking, and horse trail in Essex County, Massachusetts. ...
#10 Weir Hill
North Andover, MA
2
Weir Hill is a hiking and biking trail in North Andover, Massachusetts. It is 0.9 miles ...
#11 Maudslay State Park
Newburyport, MA
3
Right outside the seafaring town of Newburyport, Maudslay State Park encompasses a vast ...
#12 Ipswich River Trail
Topsfield, MA
3
Ipswich River Trail is a hiking trail in Topsfield, Massachusetts. It is 0.5 miles long ...
#13 Nauset Marsh Trail
Cape Cod National Seashore, MA
2
Nauset Marsh Trail is a hiking trail in Eastham, Massachusetts. It is within Cape Cod ...
#14 Mountain House Trail
Wachusett Mountain State Reservation, MA
1
Mountain House Trail is a hiking trail in Princeton, Massachusetts. It is within Wachusett ...
#15 Rockery Trail
Topsfield, MA
2
Rockery Trail is a hiking trail in Topsfield, Massachusetts. It is 0.3 miles long and ...
#16 Ward Reservation Trail
Essex County, MA
1
Ward Trail is a hiking trail in Ward Reservation, Essex County, Massachusetts. It is 0.7 ...
#17 Wyman Path
Middlesex Fells Reservation, MA
1
Wyman Path is a hiking and biking trail in Winchester, Massachusetts. It is within Middlesex ...
#18 Eliza Little Trail
Essex County, MA
1
Eliza Little Trail is a hiking, biking, and horse trail in Essex County, Massachusetts. ...
#19 Minute Man Nhp/Battle Road Trail
Minute Man National Historical Park, MA
1
Minute Man Nhp/Battle Road Trail is a hiking and biking trail in Middlesex County, Massachusetts. ...
#20 Hoyt's Trail
Trout Brook, MA
1
Hoyt's Trail is a hiking trail in Dover, Massachusetts. It is within Trout Brook. It is ...
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