A restaurateur’s view of Litchfield

Restaurateur James O’Shea buys his garden flowers from White Flower Farm in Litchfield.
Restaurateur James O’Shea buys his garden flowers from White Flower Farm in Litchfield.

To say that James O’Shea loves food is like saying a salmon loves the sea: It is not a mere enjoyment, it’s his habitat. Which is why, while gazing at hundreds of baby tomato plants displayed at White Flower Farm, a well-known mail-order nursery, his thoughts leaped to “a lovely tomato salad” prepared at the West Street Grill.

Jane Roy Brown for The Boston Globe
James O’Shea, who buys his garden flowers at White Flower Farm, posed with nursery manager Barbara Pierson.

O’Shea owns the restaurant, which occupies an old factory building opposite the Litchfield town green, with Charles Kafferman, his business partner. Now in its 23d year, the establishment became a destination for summering New York glitterati almost the day it opened, in 1990. Celebs including Kevin Bacon, Michael J. Fox, Diane Sawyer, and George Clooney have dined here. Writer Philip Roth is a patron, as was the late William Styron, who came every day. As host to the bon vivant set, O’Shea, a native of Ireland, agreed to extend this role beyond the restaurant for a day, touching down on his favorite local places in his adopted hometown.

His first stop was an errand at the studio of artist Susan Wakeen, who had completed a pair of paintings he had commissioned for the restaurant’s dining room. He had seen the works in progress, and now they were finished. The dark-haired painter stood beside O’Shea as he took in the whimsical scenes of monkeys frolicking in a park-like landscape. A golden temple glowed on a distant hilltop in the background. “I think of it as Monkey Heaven,” Wakeen explained. O’Shea pulled at his chin, head cocked, eyes flicking over the surfaces. Abruptly, he nodded. “Well done — I like them,” he announced. Wakeen beamed, and they made delivery arrangements.

Jane Roy Brown for The Boston Globe
Inside the West Street Grill, diners basked in warm light.

Then it was off to White Flower Farm, O’Shea’s source for the seasonal flowering plants that decorate the classically styled restaurant. Though technically in the town of Morris, the renowned nursery lies only 3½ miles south of Litchfield’s green. Stone walls trace the gentle roll of the old pastures in between. At the nursery “Tomato Mania” was underway, and shoppers milled outdoors between tables displaying dozens of heirloom varieties. O’Shea exchanged a hug with nursery manager Barbara Pierson, who was fielding questions from customers, but he returned to his car unburdened, having just planted his home garden, where he grows herbs and greens for the restaurant.

Get The Weekender in your inbox:
The Globe's top picks for what to see and do each weekend, in Boston and beyond.
Thank you for signing up! Sign up for more newsletters here

He needed to check on his dog, so he went by his house, a fine, rambling wood-frame antique. Built in 1785, it was “falling down” when he bought it more than 200 years later. O’Shea has spent the last 20 years restoring it. With original paneling, fireplaces, floors, and hardware, the interior is a window into affluent 18th-century life — except for the modern fixtures in the kitchen, where cookbooks overflow their shelves. Outside, behind the house, ancient trees partially shade a deep backyard, leaving a sunny opening for O’Shea’s tidy herb garden.

When he was growing up in Kenmare, County Kerry, in the late ’50s and ’60s, “everyone had a garden,” O’Shea recalled. “My parents and grandparents were into food and cooking. Everything was fresh and healthy, because it was naturally grown with farmyard manures. Irish food is about total, absolute freshness.”

Jane Roy Brown for The Boston Globe
Organic Irish salmon, cucumbers and dill piled atop potato pancakes.

The West Street Grill serves modern American cuisine — including vegetarian and vegan dishes — with French, Italian, and Asian influences. Executive chef James Cosgriff, who has presided in the kitchen for the past eight years, uses organic ingredients, fresh and locally grown or raised. O’Shea acts a sort of maestro, orchestrating the entire dining experience, from the food concept to the decor.

By late morning, O’Shea, a dedicated walker, was eager to stretch his legs. “This corner of Connecticut is famous for its walking and hiking trails,” he said. He drove 2 miles west of town to the White Memorial Foundation, a 4,000-acre conservation area on Bantam Lake, choosing a boardwalk loop that meanders through a freshwater marsh. “That’s Irish luxury, the road before you,” he quipped, gazing down the open path. He set off at a fast clip. The walk wound through reeds that rustled with unseen birds. “This place is a big draw for birders,” he said, pointing out an observation tower. In another part of the conservation area, rustic campsites stretched out along the lakeshore.


Lodging of all kinds gets stretched to capacity in July and August, when the season ramps up. Among the attractions are music, theater, and film at the restored Art Deco-style Warner Theater, in Torrington, and the three-day Litchfield Jazz Festival in Goshen, a few miles north, in August. “There is so much to do here in the summer,” said O’Shea — who, in this high season, mainly does the restaurant.

Jane Roy Brown for The Boston Globe
Across from the town green, West Street is the retail center of Litchfield.

It was well into lunchtime and O’Shea was eager to check in. Inside the West Street Grill, warm light bounced off pale yellow walls, and the buzz of conversation drifted on the breeze wafting through the open door. Kafferman spotted O’Shea and waved him over to his booth. “This is where Clooney sat,” said Kafferman. He raised a finger and a server swooped in. Soon the first of several dishes arrived: Parmesan aioli toast, the cheese browned to a crisp on top. Next, a hot soup of pureed pear and beet with a zing of ginger. A big bowl of onion rings, or “frizzled onions,” light as lace, arrived for the table. Then a plate of grilled Gulf shrimp with a salad of avocado and green beans, garnished with shaved fennel, red onion, and orange. And another specialty, house-smoked organic Irish salmon, served atop little potato pancakes with cucumber, dill, and crème fraîche.

O’Shea’s hand danced in the air, and another server leaned in close. He returned shortly, bearing little cups of homemade ice creams and sorbets on a narrow tray. “Quick,” chided Kafferman, “they’re melting.” Finally, the fabulous food stopped coming. “Come on,” O’Shea said, standing. “It’s time for another walk.”

Fortunately for the overfed, it was a stroll through West Street’s retail shops. Litchfield, long famous for its antiques and Americana, boasts several museum-quality antiques stores, several clustered around the central green, where the four main streets (North, South, East, and West) come together. This crossroads, plus its location midway between Boston and New York, gave Litchfield strategic importance during the American Revolution, when it served as an arms depot for the Continental Army. The busy times built many a local fortune. After the war, the China trade and two local schools — the Litchfield Female Academy and the country’s first law school at attorney Tapping Reeve’s residence — kept the economy humming. The signs of this early wealth remain in the form of the town’s grand 18th- and 19th-century houses, many, like O’Shea’s, now splendidly restored. The elegant Litchfield History Museum also displays art and objects from daily life during these earlier times.

O’Shea stopped in front of R. Derwin Clothiers Ladies Store, a high-end shop with two floors of casual clothing in luxe fabrics, from cashmere and leather to silk and fine cottons. Derwin’s Mens Clothing and Haberdashery, just up the street, takes the same sensibility to men’s lines. O’Shea is a customer, and here, he entered, gazed around, and said, “I love this place.”

Jane Roy Brown can be reached at