Kent, Connecticut
Looking for the best hiking in Kent? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Kent. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Kent
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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 -
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 -
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 -
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 -
Gardiner, New York
Gertrude's Nose
4.96.97 mi / 919 ft gainIt would be impossible to see all of Minnewaska’s beautiful spots in one day. Gertrude's Nose is, in my opinion, the best view in the entire park. Round trip, the hike is approximately 5 hours, and is a 7.5 mile trip. To get to the trailhead: Drive to the Minnewaska State Park entrance, pass the...Read more -
Gardiner, New York
Millbrook Mountain & Gertrude Nose loop
8.77 mi / 1253 ft gainThis great loop hike starts from the upper parking lot of Lake Minnewaska State Park. Walk towards Lake Minnewaska and once on that carriage road, turn left and follow the road to the to the opposite end of the lake. Along the way are great view points of the lake and several picnic areas for day...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 -
Stockbridge, Massachusetts
Laura's Tower and Ice Glen
5.02.4 mi / 676 ft gainYou will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods. You will reach a split in the trail, a left will take you...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 -
Woodstock, New York
Overlook Mountain Trail
4.53 mi / 1348 ft gainIt is important to know that parking for the head of this trail is great, located on Meads Mountain Rd in Woodstock NY. The trail is clearly a gravel road marked by Red trail markers, on a gradual inline up to the Hotel first, at the 2 mile mark, and then the Fire Tower is 0.5 miles further down...Read more -
Elka Park, New York
Hike to Huckleberry Point
4.54.5 mi / 644 ft gainThis is a 4.5 mile hike that is great for hikers of all skill levels. Because it is short and not overly difficult, beginners will enjoy this hike. There are some steep sections that will get your heart pumping, though, and a stunning payoff is waiting for you at the end.From the trailhead, follo...Read more -
Elka Park, New York
Hike to Plattekill Falls
0.5 mi / 137 ft gainJust outside of Elka Park, New York, Plattekill Falls is accessible from Albany and New York City alike. This is a great hike for families and all skill levels. The falls are spectacular year-round, but the best time to visit is in the spring. From the trailhead, walk left past the red house unt...Read more -
Elka Park, New York
Kaaterskill High Peak Trail
7.85 mi / 1982 ft gainThere are no direct views from the summit, so it is recommended to take the .25 mile shoot-off trail to Hurricane Ledge for beautiful views of the surrounding mountains and valleys. In the spring, wildflowers line the trail. If you look carefully in the brush, you'll find wreckage from two old pl...Read more -
Bridgeport, Connecticut
Stroll around Fayerweather Island
0.5 miParking is at the end of Barnum Road in the Seaside Park. Though the lighthouse grounds are accessible the tower itself is not open to the public. To access the island you must walk across the breakwater. Please use caution as it is uneven footing and at times can be slippery. From the isla...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 -
Elka Park, New York
Hike Indian Head Summit via Jimmy Dolan Notch Overlook
4.9 mi / 1512 ft gainThe view from the summit of this hike is incredible. Bring a sack lunch and a camera - you'll want to stay for a while! This trail is open for use year-round and provides great snowshoeing in the winter and fabulous wildflowers in the spring and summer. This is also a great location for birding!Read more