I drive about 35,000 miles each year on average - almost entirely on back roads, criss-crossing the Taconics and the Litchfield Hills. I'm lucky to live and work in one of the most beautiful parts of the country, and over the past few years I've frequently found myself mapping out road trips for friends anxious to escape the city. With that in mind, I'm hoping to occasionally share some of my favorite routes here. Thankfully Dutchess and Litchfield have really excellent tourism pages, so I'm leaving the hard work (the actual driving directions) to them. But the links I post are all routes that I have driven and enjoyed myself, and I'll offer some annotations, too.
Trip One: Litchfield Hills, "Antiquing Tour II" - featuring two(!) covered bridges. The Northwest CT tourism folks have laid out the itinerary here: http://www.litchfieldhills.com/attractions/options.jsp?oid=444.
Your GPS will probably want you to take I-84 to Route 7 to get to the starting point, but I'd suggest something slightly different. Coming from points south, take I-684 to the end, and then stay on Route 22 North. If you're hungry already, you can stop for a casual bite to eat at the famous Red Rooster Drive In, or a more serious meal at the creative and locally-minded Clocktower Grill - both about 2 miles after the end of the highway. Continue north on Route 22 until you reach Havilland Hollow Road - turn right to head east. Along Havilland Hollow Road you'll pass two important nature preserves - Michael Ciaiola Conservation Area and the newly-formed Great Hollow Nature Preserve. There's more to say about them than can be covered here - both offer excellent hiking and impressive wildlife. At the end of Havilland Hollow Road, turn left to travel north on Route 37. You'll pass through the lovely and tranquil town of Sherman, coveted by weekenders for its bucolic scenery and low taxes. Route 37 continues along, skirting the north edge of Candlewood Lake, until it arrives at Route 7 in New Milford. Turn right to follow the Housatonic towards New Milford's Green, and the intended starting point of the itinerary in the link.
Places to eat along the way:
- New Preston: the most charming miniature Main Street. Grab a sandwich at Nine Main and peruse the eclectic selection of home goods at Privet House.
- Kent: If you don't have time for a full meal at Gifford's, try the takeaway from J.P Gifford around the corner. The grilled brie and pear is worthy of a last meal. If you aren't stuffed yet, wander down to the Coffee and Chocolate Co., which delivers exactly what the name promises.
- West Cornwall: If you'd like to stop somewhere casual, The Wandering Moose is rural and friendly, with a broad menu.
- Litchfield: you'll pass through on your way back, so if it's late enough for dinner consider settling in for a proper meal at the lauded West Street Grill.
- Bantam: If it's not yet dinnertime, stop in at Arethusa Dairy for a truly decadent cup of ice cream; take a block of cheese to go.