West Street Grill: A New American Gem in Litchfield For 30 Years

On a weeknight some years ago, a hungry Bill Murray wandered into the West Street Grill on the Green in historic Litchfield. 

The “Ghostbusters” actor greeted co-owners James O’Shea and Charles Kafferman with a line like, “We heard this was the place for good food,” asking if they had a table for him and a couple friends. 

They did, and the friends turned out to be filmmaker Wes Anderson and actor George Clooney. Celebrity sightings aren’t uncommon at the Grill. In 2010, when Vanity Fair invited Philip Roth for an “Out to Lunch” interview, he chose his favorite dining spot, West Street Grill.

From the moment in May 1990 when West Street introduced urbane fine dining to well-heeled locals in Connecticut’s hilly rural paradise found—delighting sophisticated New Yorkers with country retreats—the Grill has been a haven for the affluent, famous, successful and talented. 

So it remains—but burnished by maturity and a culinary egalitarianism that has evolved naturally over the years. These days, West Street Grill draws from near and far its broadest and most diverse clientele ever.

Guests come for the stylish but comfortable setting, and for a democratized menu in which reasonably-priced upscale comfort food mingles with dishes sporting more haute flourishes—and as high summer ripens into glorious autumn in a town filled with nature preserves, antiques, shopping and other attractions, they come because word is out that the Grill is having one of those moments when everything is aligned.

Trained as a chef, the Irish-born O’Shea is a culinary impresario with panache and a knack for owning culinary moments in guiding and inspiring his kitchen. As a result, the Grill has a tradition of featuring talented chefs on the rise, rather than marquee names. Some stretches are better than others, and this is one of those.

Chef Jonathan Lobert, who helped launch the highly rated Willows restaurant at the Doubletree by Hilton near ESPN’s headquarters in Bristol, is turning out dishes that wonderfully celebrate fresh local ingredients and highlight their essential flavors without the heavy hand of showy elaboration. The purity and integrity of the tastes in each bite is welcome and refreshing.

A recent mini tasting dinner on a Sunday evening was pure delight, and a follow-up lunch on Labor Day featuring more gastro bar-style dishes was just right. On both occasions the Grill welcomed a mistral of walk-ins, and rose to the challenge without a hiccup.

Here’s a taste of some of the highlights:

The Grill’s Parmesan Aioli Peasant Bread starter is legendary, a classic since 1990 that never leaves the menu by popular demand. If you come with children as we did, this is your magic wand. Give them slices of crusty bread topped with garlic aioli and roasted Parmesan cheese and they’ll be the perfect guests for as long as you want to linger.

Almost as iconic is the heirloom tomato salad, bursting with varieties that come in many colors and offer a rainbow of subtly varying flavors. The late summer batch was from Tara Farm in Watertown, embellished with only fresh basil, extra virgin olive oil (EVOO), sea salt, and a balsamic reduction.

The local corn salad is equally simple, fresh and delicious, with the kernels, shaved from the cob, embellished by piquillo peppers, fresh basil, heirloom tomatoes, Maldon sea salt, sherry gastrique and EVOO.

Corn risotto is a standout dish for its pure concentrated flavors and wisp of inventiveness. The sweet corn is charred and the corn silk is deep fried, giving it an almost caramelized vibe. The dish is finished with Manchego and parsley.

You’ll notice there hasn’t been any meat so far in this procession, and that’s notable. O’Shea is a vegan, and the menu has lots of vegan and vegetarian dishes, though there’s no shortage of meatier choices. Still, you might be converted by dishes like the seasonal ratatouille that followed the corn risotto. Eggplant, zucchini, golden squash, local tomatoes, fresh basil, EVOO and garlic confit combined in a symphony of harmonious individual flavors. 

Our entrée in this impromptu tasting menu was a (subtle) show-stopper: day boat striped bass with pickled candy cane beets, haricot vert, cherry tomato confit, fingerling potatoes and beurre noisette. I’m not normally a fan of beets but loved these—and the fish was spectacular.

Our son dug into the Grill’s hangar steak & frites and rhapsodized about how great it was, along with the housemade frites, while our daughter destroyed the homemade ravioli with San Marzano tomato sauce. 

When three of us returned for a late lunch on Labor Day, we enjoyed the Grill’s gastro bar fare—a wonderful seared organic salmon burger & frites with lemon caper remoulade and fennel slaw, and the light and delicious fish-and-chips (Georges Bank cod, lemon aioli, bread-and-butter pickles, lemon & frites).

Glasses of rosé were perfect with both dishes. 

Our daughter, meanwhile, had a heavenly frittata.

Whether you go for dinner or lunch, make sure to save room for dessert. The vegan chocolate cake is popular, and the Grill’s crème brûlée a classic. Look especially for desserts that reflect O’Shea’s Irish heritage, which are often based on family recipes. The standout at the moment is the lemon posset, a rich lemon cream, like a light, fresh deconstructed cheesecake on the palate, topped with a lemon glaze. It’s simple and sensational.

Fall foliage season is the perfect time to venture north from Fairfield County—or come from anywhere else—and discover West Street Grill. If you’re a couple and it promises to be a warm afternoon or evening, try to snag one of the tables on the mini sidewalk patio. You never know who you might see arriving for lunch or dinner from this perch.

West Street Grill is open for lunch only Monday and Tuesday, and lunch and dinner Wednesday through Sunday. The wine list is quite nice and offers good whites, reds and bubbles by the glass. The number for reservations is 860-567-3885 and the website is weststreetgrill.com.

West Street Grill 43 West Street, Litchfield, CT 06759