North Canaan, Connecticut
Looking for the best hiking in North Canaan? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around North Canaan. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near North Canaan
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Washington, Connecticut
Hike the Mount Tom Tower Trail
1.3 mi / 337 ft gainStarting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...Read more -
Hudson, New York
High Falls Conservation Area Loop
1.41 mi / 194 ft gainHigh Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.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 -
Washington, Connecticut
Hike Meeker Trail
3.3 mi / 639 ft gainMeeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.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 -
Simsbury, Connecticut
Hike to the Heublein Tower on Talcott Mountain
4.32.54 mi / 404 ft gainThe Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...Read more -
East Nassau, New York
Kinderhook Creek
5.01.62 mi / 308 ft gainKinderhook Creek is a loop trail that takes you by a river located near Stephentown, New York.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 Fairfield, Connecticut
Hike Squantz Pond Trail
2.2 mi / 321 ft gainThe hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...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 -
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 -
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 -
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 -
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
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 -
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