Into The Would

Delicious fare at the Would

If you went to the Would in Highland, it would feel like time travel with a quirky retro setting and a simple modern menu based on quality local ingredients. You would turn into a steep driveway off a side road off Route 9W, climbing up toward imposing red brick structures that were once upon a time the Hotel di Prima, a resort for New York City Italians. Opening in 1926, it offered them a country retreat through the next few decades to play bocce, ping-pong and shuffleboard and enjoy swimming, dances, socials and camaraderie. Fifty-nine rooms boasted running water, and the main salon had conditioning; there was no heat, as it was a summer-only resort.

Claire Winslow, who has co-owned the Would with Debra Dooley since 1994, recalls summers as a child resting in what is now the main dining area, because she had asthma and it was the only part that was air-conditioned. She would gaze up at the distinctive high ceiling with oblong cutout coffers that date to the ’40s. Then the backgrounds were tile, now a shiny foil. Billowy cloth is planned to replace it.

In the winter you can dine by a crackling fire with white tablecloths and candles; in warmer weather the outdoors beckons, with outdoor seating that includes the porch, as well as a pavilion where the bocce court once was.

Winslow cooked alongside her mother in the Would’s kitchen as a child. Now she is a Culinary Institute of America-trained chef who moonlights doing corporate recipe development, and plans and executes the menu with her chef Fred Kormann, also a CIA grad, who has been there 14 years, since he came for his externship and never left. “Fred or I develop the dishes,” says Winslow. “We discuss, we taste.”

“I don’t have it all boxed in,” she adds. “I’m always trying to make it better for our guests and our staff.”

She brings back ideas for new dishes from her travels around the country: to Miami, San Francisco, Virginia, DC. “Travel always inspires me,” she says.

“Our food is with the season,” she adds. “In summer we have lots of veggies…we keep it real simple…we always try to do healthy, and we buy the best products.”

They focus on the best of what’s local. Inspiration comes from farmers’ markets like the Heart of the Hudson Valley farm market in Milton on Saturdays from 9 a.m. to 2 p.m. At the Would they serve chicken from Northwind Farms in Tivoli and produce from Hepworth Farms, an organic woman-owned farm in Milton. “And we buy the best-quality beef that we can buy,” she says.

The Would’s New American menu is an eclectic mix of simple comfort food and modern classics, ranging from mac-and-cheese to foie gras pâté on challah croustade with a fig balsamic chutney. The Would has won a gold American Culinary Federation medal and three silver ones.

At the Would you would start with a tuna Napoleon of spicy ahi tuna tartare layered with crispy gyoza and cucumber ($14), braised beef sliders with caramelized onions and a garlic rosemary aïoli ($14), Hepworth Farm kale tossed with beets, walnuts, aged goat cheese and a lemon vinaigrette ($12) or a half rack of barbecue ribs ($12). Then perhaps you would move on to pan-seared shrimp with broccoli rabe, oven-roasted tomatoes and roasted garlic tossed with linguine ($22), mushroom strudel with sautéed spinach in a roasted red pepper sauce ($22), braised beef short rib over creamy polenta ($26) or pan-seared duck breast with a raspberry gastrique ($26).

Bread is baked on-site, and desserts include, for example, chocolate peanut butter dream bar and raspberry chocolate brûlée.

A $21 prix fixe option currently offers a choice of soup, salad or calamari, followed by chicken paprikash over spaetzle, grilled mahi mahi with mango salsa or grilled hangar steak with blue cheese compound butter. This bargain includes dessert: fruit crisp, vanilla ice cream or almond cake with whipped cream and berry compote.

Or you would maybe feel like listening to soft jazz as you linger over the original long bar for cocktails or a selection from a variety of wines from a cellar of 150. The Would also offers parties and weddings on- or off-premises. Outdoor events begin the end of May.

Why “the Would”? “So people would ask questions,” Winslow answers, smiling. The resort, when owned by her parents, was named the Inn at Applewood, and customers in the 1970s dubbed the restaurant the “Wood” for short. Hence wood became would, and the Would became known for fresh, locally and naturally grown or raised ingredients, prepared simply in its own style.

The Would opens at 5 p.m. for dinner Tuesday through Saturday, and Sunday and Monday for private parties. Find it at 120 North Road in Highland, or (845) 691-9883. Read more about local cuisine and learn about new restaurants on Ulster Publishing’s or



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