Woodstock, Connecticut
Looking for the best hiking in Woodstock? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Woodstock. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Woodstock
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Simsbury, Connecticut
Hike to the Heublein Tower on Talcott Mountain
4.32.54 mi / 404 ft gainThe Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...Read more -
South Kingstown, Rhode Island
Hike the Osprey Point Loop on Trustom Pond
2 miCareful on the drive in for deer! From the parking lot head right around the Farm Field Loop Trail then continue to your right down Osprey Point Trail (0.8 miles). This is where you will most likely see the deer up close. Continue to your right to the Osprey Point Overlook, which will (on a clear...Read more -
Westerly, Rhode Island
Napatree Point Conservation Area Trail
4.03.19 mi / 82 ft gainNapatree Point Conservation Area Trail is a loop trail that takes you past scenic surroundings located near Westerly, Rhode Island.Read more -
Acton, Massachusetts
Hike the Pratt's Brook Conservation Area Loop
4.01.5 mi / 85 ft gainPark in the small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4545482, -71.4358192. The loop is very diverse wit...Read more -
East Lyme, Connecticut
Hike Rocky Neck State Park Trail
5.02.5 mi / 141 ft gainRocky Neck State Park Trail is a 2.5 mile loop hike where you may see beautiful wild flowers located near East Lyme, Connecticut.Read more -
Middletown, Connecticut
Explore Wadsworth Falls
5.00.25 miWhen it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...Read more -
Granby, Connecticut
Hiking Enders Falls
4.0Enders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut. Enders has a good sized parking lot directly on Route 219. From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...Read more -
Concord, Massachusetts
Hike around Walden Pond
4.51.69 mi / 45 ft gainPark in the lot ($8 for MA residents) by Walden Pond to access the trail, and head out either direction on the loop around the pond. Trail is accessible from April-October.Read more -
Newport, Rhode Island
Take a Stroll on the Newport Cliff Walk
4.63.5 miThe 3.5 mile Cliff Walk is a National Recreation Trail in a National Historic District. I chose to start at the western end of Easton's or First Beach at Memorial Blvd. and walk south. The first two-thirds of the walk is very easy walking conditions. Parts of the southern half of the walk are...Read more -
Deerfield, Massachusetts
South Sugarloaf Trail
1.48 mi / 404 ft gainSouth Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.Read more -
Berlin, Connecticut
Hike the Ragged Mountain Memorial Preserve
4.55.5 mi / 560 ft gainRagged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds. The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...Read more -
Randolph, Massachusetts
Hike the Ponkapoag Pond Trail
4.03.82 mi / 173 ft gainPark at the end of Ponkapoag Trail Road to access the trail. Dog friendly, open year round.Read more -
Milton, Massachusetts
Houghton's Pond Recreation Area
1.2 mi / 79 ft gainHoughton's Pond Recreation Area is a loop trail that takes you by the lake located near Milton, Massachusetts.Read more -
Meriden, Connecticut
Higby Mountain Trail
2.11 mi / 486 ft gainThe popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice! The beginning of the hike is mostly flatter land and an incline w...Read more -
Southington, Connecticut
Hike the Crescent Lake & Metacomet Trail Loop
4.02.4 mi / 269 ft gainThe hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...Read more -
Boston, Massachusetts
Run the Arnold Arboretum Trail
5.02.6 mi / 150 ft gainPark in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and summer is overwhelmingly green. There are dozens of ...Read more