15-20 mile cycle and hike loop in Litchfield County has a bit of it all! It’s hard, it’s easy, it’s up, it’s down!
Start at the top of Weber Road at the edge of Macedonia State Park. Bike along the Brook down to the entrance of the park (about 3 miles on a bit of gravel) on Macedonia Brook Road. You can also start closer to the entrance of the park if using a road bike so you don’t need to navigate the rocks downhill. Make a sharp left onto Fullertown Mountain Road.
Steep climb up the mountain where you can pause at Pond Mountain Trail as well as other entrances to trails in the state park. Only one car did I see on Fullerton Mountain Road.
Make a right onto Shiff Mountain Road and ride with caution down the hill (a few more cars on this road as well). At the bottom make a left onto River Road to the trail head of the Appalachian National Scenic Trail.
About two miles on gravel road to the trail head. Lock up the bike and enjoy a lovely walk along the Housatonic River. It’s 3-5 miles between Kent and Cornwall. Consider however you got to get back to the bike and there’s more to come!
Return to bike along the river to the town of Kent and have lunch! I have stopped at JP Gifford to grab a salad or sandwich and I highly recommend it. A definite uptick from your classic sandwiches using arugula and fresh top of the line ingredients. You can also order take out and they leave it in the box you see in view. Great for bikers and hikers! They prepped my picnic!
Return to Macedonia State park and take a well deserved break! The cascading and babbling Brook is unique at every turn!
Wow! Phew! Success!
Pivot and Pause in New England 
Your photos are fantastic, thank you for sharing.
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Thanks so much! I’m glad the info and the photos are useful to you!
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