Welcome to Kent, CT
Written & photographed by Laura Benys
Note: A version of this story originally appeared in the January 2024 issue of Connecticut Magazine.
Every year, I make a birthday pilgrimage to Kent. And every year, I imagine ways to sneak myself into this small community permanently, perhaps starting a new life as a gallerist or floral designer, or finally buying that giant loom and making bespoke tapestries.
I doubt anyone would raise an eyebrow.
Located in Connecticut’s northwest corner — in the picturesque foothills of the Berkshires, no less — Kent has a long history in farming, and was a major player in the 19th century iron industry. But over the past 50 years, this area has also become a destination for quietly artsy and eclectic living. It’s known for luring fashion designers, diplomats, actors and musicians away from nearby New York in search of the rural life.
Why? How?
Bear in mind, Kent’s village center has exactly one stoplight. But that one stoplight marshals so many of the good things in life. It’s the hub to a scenic stretch of Appalachian Trail, a string of independent shops and galleries, several acclaimed restaurants, and a piano bar. I’ll repeat that last one: piano bar.
I thought I knew everything about this place. But as with any town, no matter how many — or few — stoplights, there’s always more to discover.
SHOP
The fashion designer and long-time Kent resident Oscar de la Renta once told reporters that he couldn’t live without his weekend visits to design and antiques shop RT Facts. Actually, he said it twice. So I start here.
As I approach, Greg Randall is wrangling an impressive display of evergreens to flank the entryway. He and wife Natalie left New York to open RT Facts more than 30 years ago, originally setting up shop in Kent’s town hall. They’ve since relocated to this soaring 7,000-foot showroom, where I’m greeted by Natalie herself and, right behind her, Willa, the Randalls’ scrappy black and white terrier.
Willa keeps an eye on me as I wander the RT Facts showroom, neck craned, feeling a bit like Alice in Wonderland. There is a giant marble bust and an even more giant kinetic wooden gear sculpture, plus mirrors, mirrors, mirrors, and steel and leather accents galore. This mix of unusual antiques with sleek contemporary pieces, many made by an in-house design-build team, has made RT Facts a secret for top interior designers. There are plenty of smaller pieces, too, that casual buyers scoop up.
After I bid farewell to Willa and the Randalls, I set out to some of the other retail and gallery spaces in Kent Barns, an enclave that includes six restored historic barns. At Carol Corey Fine Art, which represents contemporary artists like New Yorker cartoonist Roz Chast, I run into a visiting gallerist from Albuquerque, New Mexico. As we admire the collection, he tells me how much he is enjoying Kent. I beam with pride, as if I have something to do with it.
Kent Barns backs up to Main Street, aka Route 7, peppered with independent shops and restaurants. (The road, which stretches from Norwalk to Massachusetts, is also a fall favorite for leaf peepers.)
I beeline to Woodford’s General Store, which specializes in locally grown and prepared grocery items, plus regional housewares. Owner Terry Crowe Deegan named the store after the Kentucky county where she grew up, and curates its selection with an instinct for Southern comfort.
I slip in amid a stream of cheerful regulars, who are picking up items like homemade pies and sweet chili bacon, and maybe a new wool throw or tea towel while they’re at it. A chandelier-like arrangement of dried hydrangeas dangles above us, created by Fairy Meadows Farm. Let’s all put more flowers on ceilings, please.
Then I swing by the Main Street mainstay Heron, which sells a colorful array of American crafts defined by “wit and whimsy,” everything from glassware to jewelry, clothing and kitchen wares. Mother-daughter team Andrea and Sophie Friedman took over in January 2023, and clearly haven’t missed a step: The place is buzzing with customers and requests. Andrea got into retail as a toy rep, so of course the children’s section is a dream. While I’m here, not one but two Corgi dog stuffed animals fly off the shelves. I’m not sure why, but this feels like an essential detail to include.
Where else should you shop in Kent?
SHOP
For me and many others, a trip to Kent means a trip to the Fife ‘N Drum Restaurant, the legacy of the late, great piano man Dolph Traymon. Back in 1973, when Kent was still the very definition of a sleepy town, Dolph opened the restaurant as a piano bar — to the utter bewilderment of his friends, who protested that Kent was the opposite of a smart place to start such a place. Dolph proved the skeptics wrong, and some 51 years later, daughter Elissa Potts still owns and runs this iconic destination, complete with live music four nights a week.
The Fife ‘N Drum has a tiny lounge area with a bar, as well as several large, fireplace-adorned dining rooms — anchored, of course, by Dolph’s Steinway piano. The menu includes flourishes like a 7,000-bottle wine cellar and a Caesar salad that’s made tableside. Honestly, it’s the little things.
Next, I visit another of my Kent favorites: the modern tavern Swyft, which serves wood-fired pizza, casual bites and inventive cocktails. The fireplace is crackling and the last of the Friday lunch crowd is lingering when I pony up to the white oak bar and ask if, pretty please, could they make me a Fox Hunt — a bourbon-based cocktail from their summer menu, which has taken up permanent lodging in my brain. They accommodate, with a smile. I love this town.
Where else should you eat in Kent?
See & Do
For all my trips to Kent, this is the first time I lay eyes on Bull’s Bridge, the supposed place where George Washington’s horse took a tumble into the Housatonic River.
We believe this because Washington, a stickler for accounting, made a note in his expense book about the cost of retrieving the horse. (Despite my best sleuthing, I cannot confirm the horse’s name, or whether it got back in the proverbial saddle after its tumble. Please write me if you have information.) Once an important crossing on the Continental Army’s supply route, Bull’s Bridge remains one of the very few functional covered bridges in Connecticut, and a prized item to cross off your New England bingo card.
A final item on that bingo card: waterfalls! Lucky you: Kent Falls State Park is home to Connecticut’s largest waterfall.
Measuring in at 250 feet tall, tumbling down more than a dozen cascades and pools along the way, Kent Falls looks like a White Mountains waterfall that up and moved to Connecticut. If you’re not feeling active, you can see it from the parking lot. But if you want to hike to the top, it’s just a quarter mile — and you can skip the gym for the rest of the week.
I choose to hike. I try to keep count of the steps that make up the rustic staircase beside the falls, but get distracted trying to control the volume of my wheezing. Luckily, I have plenty of places to catch my breath under the convenient pretense of “taking in the view,” courtesy of overlook platforms along the way. I linger at the top as the sun begins to set, trying to memorize the sound of rushing water as my moment of Zen.
By the time I trek back down to the reflecting pool at the base of the falls, and then across the little covered bridge that leads to the parking area, it’s almost dark. My hands are numb, my lungs are still tingling, and I couldn’t be happier. Another successful pilgrimage to Kent. Another reminder of the great little towns in our great little state.