Canaan
Top Spots
Hike Iron Trail
North Canaan, Connecticut
7.6 mi
/ 1 ft gain
Iron Trail is a 7.6 mile out and back hike that takes you by a river located near East Canaan, Connecticut.
Bartholomew's Cobble Trail
Sheffield, Massachusetts
3.6 mi
/ 666 ft gain
Bartholomew's Cobble Trail is a loop trail that takes you by a river located near Sheffield, Massachusetts.
Hike Stone Man Mountain Via Iron Trail
Canaan, Connecticut
2.7 mi
/ 672 ft gain
Stone Man Mountain via Iron Trail is a 2.7 mile out and back hike that takes you past great forest setting located near Falls Village, Connecticut.
Hike to Rand's View
Salisbury, Connecticut
5.3 mi
/ 1395 ft gain
Park at the Upper Falls Village Recreational Area. From the parking lot turn left onto the road. You will then take a right turn in just a moment onto the white-blazed Appalachian Trail. In a few minutes you will emerge into a small clearing. Follow the trail until it leads back into the woods.
Keep following the white blazes of the Appalachian Trail until you reach the summit of Mt. Prospec...
Hike Mount Prospect And Raccoon Hill Via Appalachian Trail
Salisbury, Connecticut
6.3 mi
/ 1 ft gain
Mount Prospect and Raccoon Hill via Appalachian Trail is a 6.3 mile out and back hike that takes you by a waterfall located near Falls Village, Connecticut.
Explore Great Falls
Canaan, Connecticut
3.0
0.5 mi
Stumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.
Hike Appalachian Trail: Bear Mountain To Race Brook Falls
Salisbury, Connecticut
9.2 mi
/ 2 ft gain
Appalachian Trail: Bear Mountain to Race Brook Falls is a 9.2 mile point-to-point hike that takes you past great forest setting located near Salisbury, Connecticut.
Bear Mountain Loop
Salisbury, Connecticut
5.0
6.05 mi
/ 1516 ft gain
At 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summit. It was built in 1885 to mark the highest "ground" in CT. It is the highest peak, but the highest...
Hike Raccoon Hill
Salisbury, Connecticut
3.2 mi
/ 570 ft gain
Raccoon Hill is a 3.2 mile out and back hike that takes you past wildlife located near Salisbury, Connecticut.
Places to stay
New Marlborough, Massachusetts
Echo Hill
This quiet, secluded camp on over 30 acres is a great place to unplug and rewind. There is also plenty to do in the towns nearby!
Echo H...
From $150 / night
Hillsdale, New York
Hillsdale Hideaway
Perched above the historic hamlet of Hillsdale, NY, enjoy your own private mountaintop with panoramic views of the Harlem Valley. Surroun...
From $125 / night
Millerton, New York
Driftways Farm
Stay at the top of a large private field with mountain views at the highest point in Dutchess County! This cozy meadow campsite is easy t...
From $125 / night
Pine Plains, New York
Hudson Valley Hilltop 2
Come soak in the panoramic views of the Catskill Mountains at Hudson Valley Hilltop! One of two private campsites on the property, this t...
From $169 / night
Pine Plains, New York
Hudson Valley Hilltop 1
Come soak in the panoramic views of the Catskill Mountains at Hudson Valley Hilltop! One of two private campsites on the property, this s...
From $169 / night
Litchfield, Connecticut
Meadow Ridge Farm Woods
Meadow Ridge Farm is a 110-acre working dairy farm. But don't be misled, the site is very secluded, located over a quarter a mile away fr...
From $135 / night
Guides and stories
Quick links
- The best hiking trails in Canaan
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- Top adventures in Canaan
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