120 North Road    Highland, NY 12528    (845) 691-9883
Tuesday - Saturday 
for Dinner
Open at 5:00

Sunday & Monday
for Private Parties
Patio Dining
Fireside Dining

120 North Road, Highland
 New York 12528
Meet the Owners
Claire & Debra
Since 1994, both Claire Winslow & Debra Dooley have combined their skills and talents, turning The Would into unique culinary eatery; the two have brought a dining experience unlike anything else seen in the Hudson Valley.
Claire Winslow 

Claire Winslow was born to be a chef.

Spending much of her childhood in the Would's kitchen with her mother and previous owner of The Would, Doris Wildrick, Claire began cooking at the age of ten. She never thought about doing anything else. She attended the Culinary Institute of America in Hyde Park, New York, participating with James Beard's Meals on Wheels program and training under world renown chefs, Bradley Ogden and Charlie Trotter. Claire's creative flair in the kitchen as won her kudos and respect from food columnists, peers, and the growing number of guests who return to the restaurant to experience her dishes.
Her take on New American Cuisine, with a touch of French flair, has earned her the title of "The Flavor Queen" by many of her colleagues. This respect and glowing admiriation has transcended the bounds of her own restaurant, winning her awards and favorable reviews from publications such as The New York Times and also being sought after to assist in such events as the Julia Child Cookbook Awards.
Claire's desire and dedication toward creating new and delicious dishes has only grown throughout years, and she isn't going to let it quit anytime soon.
Debra L. Dooley

Who better to run an incredibly seasoned restaurant than by someone who is incredibly seasoned in all shapes of life?   

Debra Dooley was born and raised in California. She moved to this area to complete college and set her career in a new, unfamliar area. Within a short period of time, Debra became the first woman ever accepted into the International Brotherhood of Electrical Workers Local 631 of Newburgh, New York, in 1979. Desiring to learn more with a hands on approach, she became involved in Construction and Property Management, which soon led her to the grounds of The Would Restaraunt. After taking over the restaurant with Claire Winslow, Debra quickly transformed The Would into a world of its own. With local artists' works on the walls and a warm glow in the dining room, Debra has created what many call the epitome of "casual elegance."

Debra has had an assertive handle on every aspect of the restaurant. Her relationship with her staff has created a family-type setting, where each member feels more at home at the end of the night than anything else. When she hostesses she greets guests with a smile and takes time to sit and chat with them while they eat. Her dedication to each facet of the restaurant even goes into The Would's Wine Cellar, which, with over 150 wines, has won the Wine Spectator Magazine's Award of Excellence every year, since 1994. And her own words: "I've developed a passion for the business...I want to learn all that I can," shows that Debra will continue to commit her efforts to The Would, so that it can bring her guests an amazing dining experience.