July 1, 2025
By Elizabeth Maker
Photographs by Visko Hatfield
It was a wild toss, opening a high-end restaurant in the hinterlands of Litchfield 35 years ago. There were maybe more farm trucks than Ferraris passing through town, and it didn’t seem most folks were drawn to fancy food.
But the Irish-born restaurateur James O’Shea, who then weekended in Warren with his husband, Charlie Kafferman, had a hunch that many with second homes hidden in the hills of the 26-town Litchfield County wanted something more.
“It was a culinary backwater,” he says, sharing memories on West Street Grill’s anniversary this year in May. “Something of a gamble, but it felt right.”
O’Shea, who had run acclaimed eateries in Ireland and New York, quickly attracted a loyal patronage including local luminaries like William Styron, Arthur Miller, Joan Rivers and Richard Widmark. The tables where those late, great legends sat now attract neighboring stars such as Kevin Bacon, Daniel Day-Lewis, and Anderson Cooper. Meryl Streep of Salisbury is a regular, and people like George Clooney, Bill Murray, and Russell Crowe have been known to grace the door.
But celebrity status is universal once you enter through the drapes of the clubby boite overlooking the historic Litchfield Green. “Everyone is treated the same, like you’re the most important, adored person,” says Daniel Glass, CEO of Glassnote Records, who’s been dining at the Grill with his wife, Deborah, since it opened in 1990. Glass, who’s signed some of the biggest names in music, including the Grammy-winning Mumford & Sons, goes to the Grill “whenever possible” when at home in Washington, he says. “We go with our two kids, three grandkids, anyone who’s in town visiting. The freshest fish, the best burgers anywhere, the incredible vegetarian and vegan dishes. It’s absolutely our favorite place.”
The Grill has long been hailed for its healthy, creative cuisine, winning awards nationwide. It was ranked one of America’s top 50 restaurants by Conde Nast Traveler, and voted the No. 1 New American Restaurant by Zagat Survey, which said, “This is the restaurant that changed Connecticut dining forever.”
At a recent dinner there, O’Shea regaled us with cocktails or mocktails, then a multi-course, wine-paired repast that included their signature cheesy charred peasant bread, mussels, Brussells sprouts, cauliflower tempura, mushroom ravioli, braised short ribs, and housemade vegan desserts: a trifecta of fruity sorbets and decadent chocolate mousse cake.
He lifted the glass off of our house-smoked Atlantic salmon, a mystical plume of heat rising above it. “It’s all about the purity and integrity of the freshest ingredients available,” he says. Wild-caught fish is delivered daily, and produce is procured whenever possible from local farms.
O’Shea knew he leaned vegan as a child growing up at his family’s seaside farm in Kenmare. “My father said, ‘James! You’re eating all the vegetables! I’m going to have to throw you over the hill with the rabbits, and you can nibble on lettuce all the day long!’”
Now, the Grill has an ever-growing cadre of younger community fans, like Litchfield financier Abraham Joseph, who goes almost every Friday after his kids’ sports practices at Rumsey Hall School in Washington. “The boys basically have a standing order for the lava cake,” he says. “The quality and execution of the food is perfection. And, sophisticated as it is, you feel like you’re home.”—weststreetgrill.com
