Middlebury, Connecticut
Top Spots in and near Middlebury
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Philipstown, New York
Hike the Osborn Loop
7.6 mi / 850 ft gainThe Osborn Loop trail itself is not a loop. It connects to a 2.5 mile section of the Appalachian Trail. Hiking these together creates the loop. Start at the trail head for the Appalachian Trail on South Mountain Pass Road. There is parking for two or three cars. Walk up the road a short dist...Read more -
Copake, New York
Bash Bish Falls from Taconic State Park
1.53 mi / 167 ft gainBash Bish Falls from Taconic State Park is an out-and-back trail that takes you by a waterfall located near Copake, New York. Swimming is not permitted at Bash Bish Falls.Read more -
Cortlandt, New York
Camp Smith Trail
4.05.92 mi / 1759 ft gainThis approximately 3-hour hike borders the Hudson River, and is one of the best in Westchester County. Start off at the parking area at the Bear Mountain Tollhouse, or at a small parking area farther up Bear Mountain Road, if you want a slightly shorter hike. The trail is fairly steep in places, ...Read more -
Cornwall, New York
Storm King Mountain Loop
4.62.44 mi / 400 ft gainThis is an easy, yet very rewarding hike with a lot of viewpoints on the way up. Technically you scale up two mountains, Butter Hill and Storm King, but most people just describe it as Storm King Mountain. This is a great hike for families with younger kids, those who don't have much time but wan...Read more -
Cornwall, New York
Hike the North Point Loop
6.5 mi / 1400 ft gainThere is three different trailheads to access the North Point Loop. I chose the trailhead that would give me the longest hike. That would be the Butter Hill parking area on Route 9W north. From the parking lot, start on the connector trail designated with white markers. Follow this for about ...Read more -
Briarcliff Manor, New York
Hike Kate Kennard Trail
1.8 mi / 140 ft gainIf you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...Read more -
Philipstown, New York
Anthony's Nose via Appalachian Trail
4.61.95 mi / 682 ft gainParking for the trail runs along both sides of 9D right up until the Bear Mountain Bridge. It can be busy on the weekends so just make sure you're as far off the road as you can and be especially careful unloading kids and dogs. The trailhead is located at approximately 41.322571, -73.975949 and ...Read more -
Cornwall-on-Hudson, New York
Hike the Stillman - Bluebird Loop
5.4 mi / 1200 ft gainThis loop hike starts at the northern trailhead of the park where the Stillman Trail begins. The parking area has enough space for only 6 or 7 cars. Start off on a wide maintained carriage road. After about a half mile, the Stillman Trail (yellow markers) breaks of to the left. However, stay ...Read more -
Pleasantville, New York
Swan Lake Loop
5.01.37 mi / 85 ft gainSwan Lake Loop is a loop trail that takes you by a lake located near Hawthorne, New York.Read more -
Bear Mountain, New York
Hike Bald Mountain, Bear Mountain State Park
4.76.8 mi / 1080 ft gainFrom your starting point at the Bear Mountain Inn, go left along the Cornell Mine Trail. (This part can be a bit confusing, but go past the carousel to a shaded picnic area; that is where the trail starts.) You will go under a bridge and follow the trail until it takes a sharp left and descends t...Read more -
Great Barrington, Massachusetts
Mt. Wilcox and Beartown Mountain Trail Loop
5.09.29 mi / 981 ft gainMt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.Read more -
Highland Falls, New York
Popolopen Torne
4.51.18 mi / 531 ft gainPopolopen Torne is a hidden gem in the Hudson Valley, a surprisingly unknown trail with a beautiful payoff and a far deeper meaning. A short hike to the top puts you at the foot of a memorial to those who have served their country, a pile of painted rocks carried up by those who want to pay their...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 -
Rye, New York
Hike the Marshlands Conservancy Loop
4.01.55 mi / 125 ft gainLocated along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...Read more