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Best Trails of Monadnock Region, NH

• Day hikes & Rail trails
• 3 to 20 mile trails
• Easy & Medium difficulties
Monadnock Region
• Driving Directions: See trail reviews

Home to the famed mountain of the same name, the region of Monadnock encompasess the banks of the Connecticut River to the west, and towns including Keene, Peterborough, Jaffrey and Hillsborough. The area features several other notable peaks offering great hikes, and is criss-crossed with a number of former railroad routes that can now be explored at will as rail trails.

We list here our favourite trails of the region, summarized below with links to our trail rreviews that feature photography and route maps that you can use on your phone for easy navigation. Did we miss your favorite trail? Let us know and we'll make sure to check it out.

Hiking Trails
Mount Monadnock 5★
Jaffrey - Dublin, NH
3.7 to 7.9 miles, Medium difficulty, Gain 1610 to 1940 feet | Excellent year-round hiking on this incredibly popular mountain. We map & describe several different approaches, including ones that will help you avoid the crowds.

Crotched Mountain 4★
Francestown, NH
3.3 to 6.8 miles, Medium difficulty, Gain 840 to 1410 feet | Named for it's notched shape, Crotched Mountain's southern slopes have several great trails. We feature the shortest route, plus a longer ridgeline ramble for you to choose from.

Fox Forest 4★
Hillsborough, NH
2.8 to 6.2 miles, Easy difficulty, Gain 350 to 1010 feet | Fox Forest is a 1,500 acre quiet woodland nature reserve and forest research station just north of Hillsborough.

Pack & North Pack Monadnock 4★
Greenfield, NH
2.7 to 7.7 miles, Medium difficulty, Gain 810 to 1360 feet | Often overshadowed by its big brother, the neighboring peaks of North Pack and Pack Monadnock shouldn't be overlooked. We're particularly fans of the 5.6 mile Ted & Carolyn Loop.

Rail Trails
Cheshire Rail Trail South 4★
Keene - Fitzwilliam, NH
20.3 miles, Medium difficulty | Relatively smooth hardpack trail with scenic and varied highlights, including the impressive railroad stone arch bridge.
Monadnock Rail Trail 4★
Jaffrey NH - Winchendon MA
8.9 miles, Medium difficulty | Heading south out of Jaffrey and crossing the state line into Massachusetts, is a mostly hardpack trail through forest and offers great views across a number of ponds and lakes.
Mason & Greenville Rail Trails 4★
Mason - Greenville NH
8.6 miles, Medium difficulty | Tranquil and rustic rail trail through woodland and close to the boyhood home of Uncle Sam. This trail gets a little bumpy at times.

Trail Map
    3★  4★  5★  ExpandMap 

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