Directions: Gaylordsville to Kent
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Depending upon which direction you're coming from there are many ways to start this loop. We're suggesting that you start out in Gaylordsville just south of Kent. At the intersection of Routes 7 and 55 go west onto Route 55. 55 will wind its way over to New York state to the town of Wingdale. (Just before the New York state border is a dirt parking lot leading up to a hiking trail. This is the start of the Appalachian Trial in Connecticut).
A few miles after going into New York you'll come upon Webatuck Village. This is a great place to check out if you find colonial craftsmanship facinating. Blacksmiths, glass-blowing, pottery, and furniture making are open to the public. This is your chance to see up close how things were made hundreds of year ago. There are shops that sell these very unique products and an old style restaurant serving traditional Yankee cuisine.
Keep on Route 55 until you come to your first intersection. (It's here that you will drive over to get on Route 22 north.) Take a left at this first intersection and go about three-tenths of a mile and take a right onto a very short street that takes you between a diner and Wingdale Elementary School. This short street takes you up to Route 22. Take a right onto Route 22 and head north. Go up to Dover Plains and at the intersection of Routes 22 and Route 4, take a right onto Route 4. Follow Route 4 until you come to the intersection of Routes 4 and 3. Go east on Route 3 which turns into Route 341 as you pass over the Connecticut border. 341 takes you right into the town of Kent and meets up with Route 7. Take a right onto Route 7 south and back to Gaylordsville where your trip began.