These pristine roads in the Kent hillside are about as scenic as the New England countryside gets. We’ve mapped a lovely 8-mile loop, skirting Pond Mountain and featuring a tough hill climb. Starting at the Kent School, climb Macedonia Road until the intersection with Macedonia Brook Road and turn RIGHT. At the fork, bear right on Fuller Mountain Road and wrap around Fuller Pond — this is the hilliest section of the route. This stretch is marked by long winding stone walls, saltbox homes, and rolling farmland views. At the next fork, bear RIGHT again on Skiff Mountain Road which winds around Pond Mountain Natural Area to the Housatonic River. Keep west along the river for a flat amble back to the start.
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- 8 mile loop
- 1040 feet
- Kent School
- Route 341
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Other Routes in Litchfield Hills, Connecticut
These long twin bike paths run from the Massachusetts border to Long Island Sound. Access paved routes from Simsbury, Avon, Collinsville, Unionville, Plainville, and Southington. The River Trail branches off the Heritage Trail for 16 miles.
Run the Litchfield Hills charming namesake town through the town green, main strip, residential streets, and the locally famous, leg crushing, Gallows Lane hill. We've mapped 3.6 and 6.8 mile options.
This enormous parcel of conservation land right in Litchfield is the go-to training zone for cross country running, with 39 miles of paths. Nice variety of terrain from forested to open to lakes. Trail running options range all abilities.
Run across the scenic dam and around the reservoir that provides water to Hartford on paved sidewalks and dirt access roads. We've mapped a 3.8 mile out and back run, but there are other trails and roads good for running in the area.
A quiet, small village with elegant homes and lovely town green is featured in this 2 mile tour of Connecticut’s back roads. Options for a longer run on pleasant, quiet side roads
Salmon Kill Road in Salisbury is arguably one of the most scenic roads in Connecticut’s northwest corner. Farmland and creekside sections, with some trail as well. We've mapped out and back or loop options.
A part of the Appalachian Trail that's good for running! We love this ~4 mile stretch of the AT along the Housatonic River between Kent and Cornwall Bridge as a flat and inviting trail run. Optional gravel road alternative/extension.
Lining the banks of the Shepaug River, Washington’s Steep Rock Preserve is trail running heaven. There's something for everyone here. We recommend the Steep Rock Loop trail out to the scenic suspension bridge and railroad tunnel.
10 mile gravel track on a former railroad bed, running through scenic bogs, lakes, and forests just south of our other Litchfield Hills routes. Choose any section of this trail and enjoy!
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