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Best trails in Littleton

704 Reviews
Looking for a great trail near Littleton, Massachusetts? AllTrails has 8 great hiking trails, walking trails, forest trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Monadnock State Park or Whitehall State Park, we've got you covered. You'll also find some great local park options, like Blue Hills Reservation or Watatic Mountain State Wildlife Area. Just looking to take a quick stroll? We've got 5 easy trails in Littleton ranging from 0.8 to 4.2 miles and from 219 to 396 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Littleton
Top trails (8)
#1 - Oak Hill
Oak Hill Conservation Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(481)
Length: 2.7 mi • Est. 1 h 20 m
Note: Offline map recommended. Users have reported that the trail is not marked well. The yellow boundary trail is 3.3 miles long. It has a few hills and lots of nice, wide flat trails. The biggest obstacles are the rocks and tree roots.Show more
#2 - Prouty Woods
Prouty Woods Community Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(55)
Length: 1.6 mi • Est. 46 m
#3 - Long Lake Park Loop
Long Lake Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(36)
Length: 3.1 mi • Est. 1 h 23 m
NOTE: On the east portion of the hike, there are open fields with bird houses. There are signs that say "NO DOGS, nesting birds". Show more
#4 - Smith Conservation Trails
Smith Conservation Land
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(31)
Length: 4.2 mi • Est. 1 h 43 m
With a new parking area on Whitcomb Avenue in Littleton, and trail loops now open on both sides of the road, Sudbury Valley Trustees' Smith Conservation Land boasts expansive views of both Beaver Brook Marsh and Black Pond Ravine. Chose between blue, red, and yellow trails. Look for tracks and signs of bobcat, porcupine, and even bear along your walk. The yellow trail along the ridge overlooking Black Pond and its stream offers wonderful birding opportunities in the spring. Continue onto additional Town of Harvard Conservation lands for a longer walk or return to the parking area via the blue trail. A red trail departs the yellow trail shortly after its beginning, and will lead you across the road, by an old farm field, and to Beaver Brook Marsh. Look across the marsh for several great blue heron nests, which promise great sights in the springtime nesting season. Look for remains of a glacial esker on your return.Show more
#5 - Sarah Doublet Forest Loop
Littleton, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(35)
Length: 1.7 mi • Est. 50 m
#6 - Hartwell Family Memorial Preserve Loop
Littleton, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(21)
Length: 1.8 mi • Est. 50 m
#7 - Whitetail Woods Loop
Littleton, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(17)
Length: 0.8 mi • Est. 22 m
#8 - Mill Hill Trail
Oak Hill Conservation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarGray Star(7)
Length: 0.9 mi • Est. 25 m