Connecticut: Killingworth to Lakeville

Route: A zip through inland Connecticut, with stops in Meriden and West Cornwall; a stay in a Winvian cottage; and a lap around Lime Rock Park. Distance: 85 miles. Car: Subaru BRZ.

The covered bridge spanning the Housatonic River in West Cornwall. 

Photo by Dominic Casserly

As a New Haven County native, I know what outsiders say about Connecticut. They think it’s a do-nothing divider between Red Sox Nation and Yankees fans, a two-hour block splitting New York from Boston. Few people aside from Manhattan train commuters truly “get” Connecticut—like how a top-notch winery can exist just minutes from the interstate. That’s fine, really—because while the masses are bored on I-84, I’m zipping from Killingworth to a racetrack in Lakeville on winding, densely forested roads that remind me of driving through Bavaria in Germany. Appropriate, then, that I’m in the new Subaru BRZ, a minimalist, rear-wheel-drive coupe built for this exact purpose.

I start on Route 148, one of my father’s favorite roads. If police ever closed it to traffic and barred abutters from leaving their homes, this hilly, squiggly stretch could be the stage for a rally race. The little Subaru tackles the curves with the grace of a figure skater—the skinny tires and quick steering almost make it too easy. Past Roast Meat Hill Road, which is an actual name of an actual thoroughfare, the next seven miles are empty. The drive is such fun that, many times through the years, I’ve doubled back and done it again.

In Middlefield, I stop at Lyman Orchards, an eighth–generation family farm that’s so popular it takes phone reservations for pumpkin pie. From there I head west on Route 68. It’s like driving a paved sine wave—you power up the hills and ease down again and again, the engine revving to keep pace. That winery I mentioned? Make a left at the wine-trail sign on 68, stop at Gouveia Vineyards in Wallingford, and prepare for flashbacks of Napa Valley. The barbecue trailer in Donald Washington’s driveway in Meriden is another worthy deviation from 68. He’s open only Thursday through Saturday, because the rest of the week the former Pratt & Whitney engineer is burning hickory and smoking pigs “just like they do in the South,” he says. Customers travel from across New England to sample his pulled pork and sauces.

I divert to Upper Whittemore Road via Route 63 and end up at a deserted intersection with six stop signs and no street names. Heading straight, I catch glimpses of Lake Quassapaug and soon enter the sleepy “Christmas Town” of Bethlehem, where the post office is inundated around the holidays with card senders seeking the holy postmark. Then, out of nowhere, is the gated Winvian resort in Morris. Here, you stay in one of 18 private wooded cottages—each commissioned by a separate architect—like the tree house suspended 34 feet off the ground, or the music house adorned with marimba resonators (there’s also a spa and door-to-cottage room service).

I’ve seen the postcard-perfect center of Litchfield a dozen times, so I press on to Route 45 toward West Cornwall, a tiny town with an enormous covered bridge, a café, and the eclectic Wish House boutique, packed with home accents and funky clothing. From here, arching tree limbs whip over my head on Route 7, the road glistening after a rain shower. Lime Rock Park is ahead, a historical 1.5-mile racetrack that hosts the famous American Le Mans Series (and can host you, too, with a one-day pass to Skip Barber Racing School). But even if you fancy yourself a racecar driver, please don’t crowd my dad’s roads.

Back roads and farmland in Bethlehem.

Photo by Dominic Casserly

Wine tasting with a view at Gouveia Vineyards in Wallingford. 

Photo by Dominic Casserly

Crossing the Cornwall Bridge with the hills of Housatonic Meadows State Park beyond.

Photo by Dominic Casserly

A cow pokes its head out of a barn at Mid Valley Acres in Killingworth.

Photo by Dominic Casserly

Check out all five New England road trip routes in our 2012 Fall Travel Guide.