221 Trails in Massachusetts
| Rank | Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|---|
| 51. | Dogtown | Advanced | 15.0 |  |
Gloucester |
| 52. | Chebacco Woods | Intermediate | 10.0 |  |
Hamilton |
| 53. | Hopkinton State Park | Intermediate | 10.0 |  |
Hopkinton |
| 54. | Hale Reservation | Beginner | 10.0 | |
Westwood |
| 55. | Georgetown-rowley State Forest | Intermediate | 9.0 | |
Georgetown |
| 56. | Pearl Hill State Park | Beginner | 20.0 | |
Townsend |
| 57. | Franklin State Forest | Intermediate | 7.0 | |
Franklin State Forest |
| 58. | Carolina Hill | Intermediate | 10.0 | |
Marshfield |
| 59. | Dubuque State Forest | Advanced | 16.0 | |
Hawley |
| 60. | Ice Houce (Sawmill Hills Conservation Area) | Advanced | 15 | |
Florence |
| 61. | West Hill Dam | Intermediate | 5.0 | |
Upton |
| 62. | Bald Hill Reservation | Beginner | 10.0 | |
Boxford |
| 63. | Granville Gorge | Intermediate | 8.0 | |
Granville |
| 64. | Ward Reservation | Intermediate | 12.0 | |
Andover |
| 65. | Nickerson State Park | Beginner | 20.0 | |
Brewster |
| 66. | Ashland State Park | Intermediate | 7.0 | |
Ashland |
| 67. | Groton Town Forest | Beginner | 6.0 | |
Leominster |
| 68. | Willow Street Trails | Intermediate | 15.0 | |
Yarmouth |
| 69. | Prospect Hill | Beginner | 10.0 | |
Waltham |
| 70. | Freetown State Forest (Bent Rim Trail) | Intermediate | 4.0 | |
Freetown |
| 71. | Mt toby | Intermediate | 16.0 | |
Sunderland |
| 72. | Upton State Forest | Beginner | 12.0 | |
Upton |
| 73. | Beverly Commons | Advanced | 10 | |
Beverly |
| 74. | Rutland State Forest | Beginner | 6.0 | |
Rutland |
| 75. | Bradley Palmer | Beginner | 11.0 | |
Topsfield |
| 76. | Ames Nowell | Intermediate | 10.0 | |
Abington |
| 77. | Grafton Land Trust | Intermediate | 20.0 | |
Grafton |
| 78. | Mendon Town Forest | Intermediate | 7.0 | |
Mendon |
| 79. | Oak Hill | Advanced | 8.0 | |
Littleton |
| 80. | DAR | Advanced | 16.0 | |
Goshen |
| 81. | Myles Standish Forest | Beginner | 100.0 | |
Plymouth |
| 82. | Rocky Mountain And Highland Park | Beginner | 30.0 | |
Greenfield |
| 83. | Beaver Brook North | Intermediate | 4.0 | |
Belmont |
| 84. | Charles River Loop | Easiest | 15 | |
Boston |
| 85. | Maudslay State Park | Intermediate | 4.0 | |
Newburyport |
| 86. | Vaughn Hill/bower Spring Trail System(s) | Advanced | 4.0 | |
Bolton/harvard |
| 87. | Red Zone (Charlemont trails) | Advanced | 3.0 | |
Charlemont |
| 88. | Sutton Water Works | Intermediate | 5.0 | |
Sutton |
| 89. | Holyoke Range Trails | Intermediate | 15.0 | |
Amherst |
| 90. | Bachelor Street Trails | Advanced | 15.0 | |
Granby |
| 91. | Manhan Rail Trail | 10.0 | |
Easthampton | |
| 92. | Middle Distance Trail | Intermediate | 5.0 | |
Deerfield |
| 93. | Merrimack River Trail | Beginner | 10.0 | |
Andover |
| 94. | Henry S. Hunnewell Town Forest | Intermediate | 1.0 | |
Natick |
| 95. | Wma Trail | Beginner | 3.0 | |
Wilbraham |
| 96. | Boynton Park | Intermediate | 3.0 | |
Worcester |
| 97. | Caryl Park | Beginner | 17.0 | |
Dover |
| 98. | E-stranged Moose | Intermediate | 2.0 | |
Charlemont |
| 99. | Nobscot Mtn. | Intermediate | 15.0 | |
Sudbury |
| 100. | Facing Rocks | Intermediate | 7.0 | |
Ludlow |
