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Photo by Victoria Saint Martin / Courtesy of City Winery

5 Orange County Eateries to Dine at During Hudson Valley Restaurant Week


Are you ready for the return of Hudson Valley Restaurant Week? This May 10-23, the region’s premier dining event kicks off with new restaurants, new menus, and socially distant dining options available for everyone. In Orange County, local restaurants turn up the heat with fresh ingredients, innovative offerings, and tempting specials. So what are you waiting for? Browse through some of our top picks in Orange County, then browse our full list of participating restaurants here.

Café Pitti

40 Front Street, Newburgh

Can’t get enough of Italian cuisine? Café Pitti is the spot for you this Hudson Valley Restaurant Week. Stop by the eatery during lunch or dinner to take in the views from the Newburgh waterfront while dining on wood-fired pizzas and Italian classics alongside a velvety glass of wine. While Café Pitti hasn’t unveiled its full HVRW menu yet, get excited for authentic Italian bites from start to finish. If dishes like scamorza pizza with cremini mushrooms and stuffed focaccia with robiola and white truffle oil on the regular menu are any indication, then this Newburgh hotspot is sure to be a can’t-miss destination during Restaurant Week.

The Chianti Cow
Photo courtesy of The Chianti Cow Restaurant

The Chianti Cow Restaurant

1483 Route 6, Port Jervis

A favorite for fine family dining in Port Jervis, this Orange County eatery specializes in American cuisine made with the freshest ingredients around. For Hudson Valley Restaurant Week, it pulls out all the stops with bites like pan-fried Brussels sprouts tossed with roasted garlic and seafood arancini stuffed with shrimp and calamari. And that’s just to start! Moving onto mains, the harvest chicken with roasted garlic polenta and the pan-seared salmon are both worthwhile entrees. The Chianti Cow serves its HVRW menu during dinner throughout the week, with a special lunch menu available on the weekends as well.

City Winery
Courtesy of City Winery

City Winery

23 Factory Street, Montgomery

If you haven’t stopped by Orange County’s hottest new winery yet, make Hudson Valley Restaurant Week your chance to do so. The Mongomery winery and restaurant serves its menu for lunch on Saturday and Sunday and for dinner on Thursday and Friday, so book reservations in advance for dine-in or outdoor seating. On the dinner menu, diners can hop from starters like chilled gazpacho and summer salads to mains like margherita flatbreads and grilled flatiron steaks to desserts like lemon bars and strawberry biscuit shortcakes. Plus, since this is City Winery, it only makes sense to order the recommended $15 wine flight, which includes seyval blanc, Chardonnay, Rhone-style red blend, and merlot.

J's Place
Courtesy of J’s Place

J’s Place

39 W Main Street, Middletown

With a Hudson Valley Restaurant Week dinner menu available Wednesday through Monday, J’s Place is a great pick for anyone who wants to dine outside this May. The Middletown eatery does HVRW right with a starting spread that includes spring berry salad and lemony chicken soup. The second course is all about the meat, with options ranging from beef carbonara to chicken saltimbocca to Mediterranean shrimp with risotto. By the time dessert arrives, diners will have a hard time choosing between a chocolate raspberry mouse topped with whipped cream and a coconut custard tart that’s finished with a chocolate drizzle.

Oak & Reed

45-53 North Street, Middletown

Not ready to dine out quite yet? Oak & Reed gets it, which is why it offers its Restaurant Week menu for both dine-in and takeout. Speaking of the menu, the Middletown restaurant serves its HVRW menu for lunch on Wednesday through Friday, giving locals the perfect excuse to make the most of their lunch break. Go for appetizers like the Korean fried broccoli or cream of asparagus soup before moving onto jerked pork belly or spring pea risotto for the main. When it’s time for dessert, the carrot cake with cream cheese frosting and walnuts is a surefire hit.

Hudson Valley Restaurant Week is back this April 8-21!