Weston, Connecticut
Looking for the best hiking in Weston? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Weston. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Weston
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Englewood Cliffs, New Jersey
Hike the Dyckman Hill/Carpenter's Grove Loop
4.04 mi / 400 ft gainThis loop hike can be started from several different places. I chose to start from Allison Park which overlooks the Hudson River in Englewood Cliffs, NJ. From the parking area, walk out to the entrance road and travel south to Saint Peter's College. The Long Path Trail, which you join from All...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 -
Dover Plains, New York
Hike Dover's Stone Church
4.5Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...Read more -
New Windsor, New York
Jessup/West Ridge Loop via the Sweet Clover Trail
9.17 mi / 1916 ft gainSchunnemunk Mountain State Park is one of my favorite parks. It offers many trails and possibilities for different loops. The attraction of Schunnemunk Mountain is the long double ridges running parallel to each other and amazing views in all directions. This hike starts at the Taylor Road par...Read more -
Kent, Connecticut
Hike the Ridge Loop Trail, Macedonia Brook SP
3.0For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...Read more -
Kent, Connecticut
Explore Kent Falls
5.00.75 mi / 250 ft gainEvery now and then you need a day to rest those sore muscle from all your recent adventures. The only issue is, you don't want to sit around inside, you want to be outside. Insert a trip to Kent Fall State Park. The perfect rest adventure day.Located 1 hour and 45 minutes north of New York City i...Read more -
Ridgewood, New Jersey
Saddle River Trail
5.0Saddle River Trail is an out-and-back trail that takes you by a lake located near Fair Lawn, New Jersey.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 -
Allendale, New Jersey
Celery Farm Mayor Fitzpatrick Nature Trail
3.01.2 mi / 92 ft gainThe Celery Farm Mayor Fitzpatrick Nature Trail in Allendale, New Jersey, is a peaceful, scenic retreat for birdwatchers, hikers, and nature lovers. This 1-mile loop trail winds through a 107-acre freshwater wetland preserve, offering opportunities to spot over 240 bird species, deer, turtles, a...Read more -
Patchogue, New York
Fire Island's Watch Hill
4.02 miIf departing from NYC, catch the early LIRR train from Penn Station (or Atlantic Terminal) towards Patchogue. You may have to transfer at both Jamaica & Babylon, but it's an easy hop across the platform. Trip will take approximately an hour and a half and cost around $15, Off Peak, each way. ...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 -
New York, New York
Jacqueline Kennedy Onassis Reservoir Running Path
5.01.68 mi / 69 ft gainJacqueline Kennedy Onassis Reservoir Running Path is a loop trail that takes you by a lake located near New York City, New York.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 -
New York, New York
Northwest Central Park Loop
3.63 mi / 164 ft gainThe Northwest Central Park Loop in New York City offers a scenic, family-friendly experience through some of the park’s quieter sections. The loop features well-maintained paths, stunning views of the surrounding nature, and landmarks like the Reservoir. It’s perfect for walking, jogging, or ca...Read more -
Monroe, New York
Hike the Jessup/Highlands/Long Path Trails
7.8 mi / 500 ft gainThis trails starts at a small park in Woodbury called Gonzaga Park. Closed from mid-November to April, you are still able to park just outside the gate if that is the time of year you are hiking. Three different trail names share this path. The Jessup trail starts/end at Gonzaga Park and trave...Read more -
608 Ramapo Valley Road, New Jersey
Hike the Halifax Trail and Ruins in the Ramapo Valley Reservation
8.25 mi / 500 ft gainTo start, I recommend coming in the early morning or afternoon, as the parking lot fills up with people hiking, fishing or going for a walk with their family. I usually get my luckiest before 9. This park is as relaxing or exciting as you want to make it. Here is a good map to use/ print out. We ...Read more