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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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 -
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 -
New Paltz, New York
Hike Mohonk Preserve's Gatehouse to Skytop Tower
5.09 mi / 1268 ft gainBegin at the intersection of Gatehouse Rd and Mohonk Private Rd. There is a small shoulder to park on here. Begin hiking into the preserve along the gatehouse road. There will be signs stating you need a membership or pass to enter. Don't worry about these, there will be a place on the trail ...Read more -
High Falls, New York
Mohonk Mountain House Labyrinth and Lemon Squeeze Hike
4.5Mohonk Mountain House is a historic resort located just outside the Catskills in the Hudson Valley just 90 miles north of New York City. With 85 miles of winding trails throughout the Mohonk Preserve, you'll have endless hiking options upon your arrival.Parking at the Gatehouse is limited, so be ...Read more -
Danbury, Connecticut
Hike Middle Mountain To Thomas Mountain Loop
3.7 mi / 856 ft gainMiddle Mountain to Thomas Mountain Loop is a 3.7 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.Read more -
Glastonbury, Connecticut
Hike the Cotton Hollow Nature Preserve
5.03 miThere are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...Read more -
Hampden, Massachusetts
Goat Rock Trail
2.67 mi / 659 ft gainGoat Rock Trail is an out-and-back trail where you may see beautiful wildflowers located near Hampden, Massachusetts.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 -
Hamden, Connecticut
Hike the Tower Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...Read more -
Hamden, Connecticut
Hike the Mill River Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSince I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...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 -
Hamden, Connecticut
Boulder & Free Climb off the Blue Trail In Sleeping Giant SP
Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...Read more -
Beacon, New York
Hudson Highlands Overlook Trail
3.29 mi / 1017 ft gainHudson Highlands Overlook Trail is an out-and-back trail that takes you through a nice forest located near Beacon, New York.Read more -
Ridgefield, Connecticut
Hike the Hemlock Hills & Pine Mountain Loop
5.07.5 mi / 1174 ft gainThere are several trailheads for Hemlock Hills But the least crowded is at the intersection of Ned's Mountain road and Bogus Road. I took my 3 year old black lab. There are ton's of little ponds for your dog to jump in and do dog things. For the most part the hike is flat but at some parts it c...Read more -
Beacon, New York
Hike Fishkill Ridge
Fishkill Ridge is a strenuous but rewarding hike, and one of the less known areas in the Hudson Valley. The parking area is at the very end of Sunnyside Road in Beacon, along with the information board at the trailhead. The red trail leaves the lot and will take you up to the first peak on the ri...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