Stockbridge, Massachusetts
Looking for the best hiking in Stockbridge? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Stockbridge. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Stockbridge
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Williamstown, Massachusetts
Mount Greylock via Money Brook Trail
9.57 mi / 2849.96 ft gainPark in the parking lot on Hopper Rd. Walk to the end of the road where you will find the Hopper Trailhead. Take the right fork. The Money Brook trail will take you to a waterfall, the Mt. Greylock summit, and back to the end of Hopper Rd. The trail is long but worth the hike, exploring parts of ...Read more -
Savoy, Massachusetts
Tannery Falls Loop
0.54 mi / 135 ft gainThe hike to Tannery Falls may be a little confusing, I'll clear it up for you before you even go there! To get to The falls you will travel down a dirt road that isn't very well maintained during the winter. As you keep driving down the dirt road you will notice a pond , which means you are almos...Read more -
North Adams, Massachusetts
The Cascades Trail
4.31.97 mi / 315 ft gainThe Cascades Trail is an out-and-back trail that takes you by a waterfall located near North Adams, Massachusetts.Read more -
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 -
Granby, Connecticut
Enders Falls
4.00.5 mi / 118 ft gainEnders 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 -
Cropseyville, New York
Hike Dickinson Hill Fire Tower
4.53 mi / 200 ft gainOnce you drive onto N. Long Pond Road you will follow it appproximately 1.5 miles to the end. From the parking you can take the short walk back on the road to the start of the trail. The trail is actually a rough Fire Tower Road. You will follow this for about 1.3 miles. Here you will see a se...Read more -
Holyoke, Massachusetts
Whiting Street Reservoir Loop
3.74 mi / 138 ft gainWhiting Street Reservoir Loop is a loop trail that takes you by a lake located near Holyoke, Massachusetts.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 -
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 -
Greene County, United States
Hike to Newman's Ledge
4 mi / 584 ft gainLocated in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...Read more -
Tannersville, New York
North Mountain
4.76.16 mi / 1060 ft gainHave you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills. Par...Read more -
Palenville, New York
Kaaterskill Falls via Laurel House
4.51.67 mi / 360.89 ft gainThis short hike is one of the most popular in the Catskills — and for good reason. From the Laurel House Road Trailhead, it’s less than a mile round trip to reach Kaaterskill Falls, New York’s tallest two-tiered waterfall, with a dramatic 260-foot drop into a rocky amphitheater. The trail itse...Read more -
Elka Park, New York
Layman's Monument and Kaaterskill Falls
3.05 mi / 892 ft gainLayman's Monument and Kaaterskill Falls is an out-and-back trail that takes you to one of New York's tallest waterfalls at 231 feet and to the historical monument for Frank D. Layman, who passed away in 1990 while fighting a forest fire. This trail is located near Haines Falls, New York.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 -
Albany, New York
Blueberry Hill East
1.73 mi / 59 ft gainBlueberry Hill East is a loop trail where you may see beautiful wildflowers located near Albany, New York.Read more -
Tannersville, New York
Kaaterskill Rail Trail + Kaaterskill Falls
5.03.61 mi / 246 ft gainThe Kaaterskill Rail Trail begins near Haines Falls, New York heading toward North and South Lake. The trail is set in a gorgeous forest, and is used for hiking, trail running, and birding trips. The trail provides exceptional views of the surrounding mountains, valleys, forests, and towns.Read more