CHESTER Restaurant opened on May 12, 1998 and was located in an 1840’s Greek- Revival captain’s house in Provincetown’s East End arts’ district.  CHESTER was the creation of John F. Guerra and Jay Coburn, refugees from the Washington, D.C. political scene.   With absolutely no restaurant experience other than as frequent diners, Jay & John created CHESTER from their love of exquisite food and wine as well as their love of throwing dinner parties for friends.  Prior to moving to Provincetown in 1997, John was in the U.S. Foreign Service and Jay served as a lobbyist for community-based AIDS organizations.   After nine glorious seasons, CHESTER closed its doors on October 29, 2006.  CHESTER was named after Jay and John’s beloved Airedale Terrier who died at age 14 in June of 2003. 

Chef-owned CHESTER Restaurant set new standards for gourmet dining on Cape Cod and, at its pinnacle, was the finest restaurant on the Outer Cape.   CHESTER received the highest food and service ratings for Cape Cod restaurants in the nationally-recognized Zagat Survey from 2002 to 2006.  Further, in 2004 & 2006, CHESTER and was named “Best Restaurant on the Cape for General Excellence” by Boston Magazine.

CHESTER emphasized fresh, carefully prepared food, accompanied by an extensive selection of intriguing wines. The seasonally-changing American menu and weekly specials featured the finest in locally and regionally procured products, including locally grown organic produce, Chatham cod, Cape Cod scallops, Provincetown lobster, Vermont quail and grass fed beef and farmstead cheeses from small New England producers.  Chef Jay and his talented team, which included Lenny Berner and Steven Kacmarcik, combined these great ingredients with classic techniques to produce delicious and artfully- presented dishes. Desserts were made in-house by pastry chef Jacqueline Hunter, and included an array of seasonal ice creams, sorbets and tarts, as well as a signature molten bittersweet chocolate cake.

CHESTER’s list of over 200 wines was the largest on the Outer Cape and garnered several  Wine Spectator Awards of Excellence starting in 1999. CHESTER was the only restaurant on the Outer Cape to age its wines in a temperature and humidity controlled cellar.  The list featured selections from the world’s major wine-producing regions and included many smaller producers not commonly seen elsewhere on the Cape.  Jay & John spent time at many of the wineries, and John was particularly generous in sharing the personality of the people and places who made many of the wines on the list. John enthusiastically shared his extensive knowledge and experience with these wines, helping guests enjoy intriguing pairings of food and wine.

The candle-lit dining room, with its ochre-hued walls (FYI:  the color was Benjamin Moore 313) and banquette seating, offered an elegantly relaxed experience not unlike a dinner party with special friends. A lovely out door garden was added in 2000. The attentive service at Chester was modeled on the service of New York City’s famed restaurants Union Square Café and Gramercy Tavern.  Fortunately for CHESTER guests, an extraordinary group of gracious and enthusiastic, servers worked at the restaurant over the years.  Guests’ favorites included Jimmy Broussard (now manager at Abbicci in Yarmouthport), Audrey Mostaghim (now a sommelier at Topper’s at the Wauwinet on Nantucket), Dylan Bertram (also now at the Wauwinet), Robert Worster (now at Mohegan Sun), our fantastic bartender Dan “Large Marge” Coburn, and, last but never least our extraordinary red-headed muse, Dianna Cavalieri.

In the fall of 2005, Jay and John reached the conclusion that they had taken CHESTER as far as they could.  The time had come to turn CHESTER over to new owners, or failing that, to exit at the top of their game.  After a final, memorable season, John and Jay decided that it was best to go out on top.  Sunday, October 29th 2006 was the final night at CHESTER and it featured a ten course gala menu enjoyed my many of the restaurant’s loyal fans.  The former home of CHESTER Restaurant at 404 Commercial Street continues as a restaurant (as it has since the 1950s), under new ownership and with a different name.

John and Jay now enjoy a much more relaxed pace with Airedales Harrison (Chester’s son) and Adelaide.  John enjoys reading, writing, travel and tending to his family business interests in the Rio Grande Valley of Texas. Jay is a ski instructor at Stowe Mountain Resort during the winter months.  In the summer, however, CHESTER lives on through CHESTER at Home, Jay’s private chef business.  As time permits, Jay and John continue their tradition of dinner parties for friends in their home in South Truro.