Roxbury, Connecticut
Looking for the best running in Roxbury? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Roxbury. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Running Spots in and near Roxbury
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Sharon, Connecticut
Hike the Pine Knob Loop, Housatonic Meadows SP
5.02.5 mi / 770 ft gainThe Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick woods filled with vistas, wild flowers and tons of wild life. You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...Read more -
Pound Ridge, New York
Leatherman's Loop
1.25 mi / 1183 ft gainThis loop trail is moderately rated and reaches a total elevation gain of approximately 1,183 feet. It’s located in the Ward Pound Ridge Reservation, which spans roughly 4,315 acres. It is Westchester County’s largest park and includes roughly 35 plus miles of hiking trails to explore. The Ward...Read more -
Meriden, Connecticut
Hike the Metacomet, Blue, and Yellow Loop
5.04.5 mi / 976 ft gainStart from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...Read more -
Kent, New York
King's Chamber and Moose Hill Loop
3.14 mi / 499 ft gainKing's Chamber and Moose Hill Loop is a loop trail that takes you by a lake located near Carmel, New York.Read more -
Stamford, Connecticut
Hike Cove Island Park Loop Trail
5.01.1 mi / 3 ft gainThis trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...Read more -
Beacon, New York
Explore Long Dock and Dennings Point Parks
4.0Long Dock and Dennings Point are two of the most popular parks in Beacon, that just so happen to be connected by a train track turned trail. Plenty of parking is available at Long Dock, and its a perfect spot to picnic, launch your kayak into the Hudson, or cast your line hoping to reel in the bi...Read more -
Mount Washington, Massachusetts
Mount Frissell and Brace Mountain Loop Trail
5.08 mi / 807 ft gainMount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.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 -
Manchester, Connecticut
Explore Wickham Park
5.0Wickham Park Is open the first weekend in April and closes the last weekend in October. Entrances fees are $5 Monday-Friday and $7 Saturday-Sunday. The park is known for its 250 acres of open fields, wildflowers, gardens, ponds and nature center. There is no where else can you go have a picnic w...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 -
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 -
Yonkers, New York
Run the Old Croton Aqueduct Trail
5.026.5 miThis trail traces the route of the Old Croton Aqueduct, which carried water to New York City between 1842 and 1955. Our recommended route starts near the Greystone Station in Yonkers, NY (Metro-North Hudson Line) and ends by the Scarborough Station, but you can easily modify your route – the enti...Read more -
Gardiner, New York
Lake Minnewaska Loop Trail
2.01 mi / 348 ft gainLake Minnewaska Loop Trail is a loop trail where you may see beautiful wildflowers located near Kerhonkson, New York.Read more