The Hills Are Alive | Patrick Donegan - October 2019

October 23, 2019

The Hills Are Alive  |  Patrick Donegan - October 2019

The start of autumn whirls in with the same familiar images of amber and crimson leaves, covered bridges, weathered barns, and pumpkin patches. More often than not, the spotlight is on states like Vermont and New Hampshire, and for good reason; these northern states certainly do shine in the few short months of fall. But there’s another New England treasure just a little further south that deserves its fair share of attention – the Litchfield Hills of Connecticut.

Growing up in southern Connecticut, I didn’t have a whole lot of exposure to the great towns in the northwest portion of the state. But as I got older and started to explore more, I simply fell in love with this area located just an hour away from me. Seated at the foot of the Berkshires, the Litchfield Hills are known for their distinct rural scenery, including quaint town greens, historical architecture, and of course, stunning fall foliage. Follow along as I share some highlights from a recent day trip I took to this truly special place.

With a late start to the day, I began my journey upstate and headed up Route 7 to Kent – one of my personal favorite towns in the area. Yankee Magazine named Kent the best town in New England for fall foliage, and it lives up to this distinction. Starting from Bull’s Bridge, one of the town’s two covered bridges, all the way through Main St, I was simply awestruck by how colorful the surrounding hillsides and mountains already were.

After walking past bookstores, antique shops, and a number of restaurants, I continued on my way to the quiet town of Cornwall, known for its red covered bridge. I was greeted at the bridge by a handful of other photographers who had the same idea as me. While most of the foliage around the bridge was still green, it was still a gorgeous sight to see with the Housatonic River running underneath.

From Cornwall, I made my way through the little town of Goshen, known for its annual fair  on Labor Day weekend, drawing some tens of thousands of people each year. Only a few short minutes later, I ended up in the last stop on my trip: Litchfield. Litchfield’s town green, situated between East Street and West Street, is lined with fantastic restaurants and shops (for food, I recommend @ the Corner  and The Village , and for shopping, I recommend R. Derwin Clothiers). No trip to Litchfield is complete without a drive through North Street and South Street to admire the stunning colonial homes and a pit stop at Arethusa Farm, home of some of the best dairy in the state of Connecticut (their ice cream and eggnog is some of the best you’ll ever have).

And just like that, my perfect fall day came to an end. If you ever find yourself in need of the perfect autumn getaway, all you need to do is take a step back and listen – the hills are calling…


Patrick Donegan (@patrickdonegan)


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