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West Street Grill

One of America’s Top 50 Restaurants – in Litchfield

They are the perfect couple to run a restaurant. James O’Shea, renowned Irish chef, is in charge of creating the sensational fare offered at the West Street Grill. Charlie Kafferman, whose career was in the fashion business, is the consummate host, inviting and charming each diner with his smile and his jokes. Together they have made their restaurant a home away from home for locals and visitors for almost 30 years.

O’Shea came from Ireland in 1978 and was eager to be part of the burgeoning food world in America. “My family was very involved in the food industry in Ireland,” he explains. “My grandmother grew up in a large country store; my great aunt had a grocery store; my mother’s family had an inn and a butcher shop; and my father had two small farms. We were essentially the town’s grocery service people.”

O’Shea and Kafferman met through mutual friends—appropriately in a restaurant. They rented a house on Lake Waramaug in 1979 and got acquainted with Litchfield County. O’Shea kept feeling that the area needed a really good restaurant. At that time New York City was in the throes of the new American cooking wave and good food and fine restaurants had become a favorite pastime.

“The Litchfield Green, at the time, was very quiet and there was talk that people who were tired of the Hamptons might start looking at places in Litchfield County,” says O’Shea. “There was a restaurant in this space, but it was more of a diner. When the space became available, we decided we should go for it. I wanted to do simple food but with the highest quality amazing ingredients: the best hamburger on a homemade bun, with homemade pickles and handmade fries. We opened for lunch on May 14, 1990, and for dinner on Memorial Day two weeks later.”

And, as they say, the rest is history. The Grill was discovered by the locals and weekenders alike. The restaurant was more formal than it is today and people loved getting dressed up and going out for dinner. It became the place to go and it was an incredible eclectic mix of people.

“We were discovered early on by Alexander Liberman, who was editorial director at Vogue, and his wife Tatiana, who lived in Warren. At the time the area was popular with many writers and artists who frequented the Grill; William Styron was a mainstay, as was Arthur Miller, Philip Roth, David McCullough, Stuart Woods, Alexander Calder, Richard Widmark, Mia Farrow. The BBC filmed a piece on Arthur Miller in the restaurant. They liked coming here because they could hang out, get good food, nice wines, and nobody would bother them. The other clientele respected their privacy.”

Over the years the restaurant has garnered rave reviews and was named one of America’s top 50 restaurants by Condé Nast Traveler and voted the number one New American Restaurant in Connecticut by Zagat Survey. O’Shea himself got an award from the governor for changing the way Connecticut dines.

West Street Grill is a mainstay on the Litchfield green and an integral part of its makeup.

The restaurant is more casual now and the young people who have recently settled here have quickly discovered it. They want simpler things, but with excellent ingredients and masterfully prepared. And they can find it here. “Litchfield is a charming, well planned village,” says O’Shea, “one of the most beautiful you can find. It represents a great history and character, and a great cross section of people.”

But, best of all, it has the West Street Grill.



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