Orange County Wine Trips

Itineraries to help you explore Hudson Valley wine country.

Every visit to Hudson Valley Wine Country should include a stop at Brotherhood Winery in Washingtonville, America’s oldest continuously operating winery since 1839. Take the tour and go down into the cellars, where you will see on display historic winemaking equipment and learn about the history of the winery. Brotherhood has a complete line of sparkling wines, varietal wines, red, white, rosé, and hard cider. It also hosts many festivals during the year, including its end-of-summer grape stomping weekends, wine and sangria pig roast, and Halloween party.

Palaia Winery
Palaia Winery Photo by Jan Palaggi

A 15-minute drive will take you back in time, to when it was all about peace, love, and rock ’n’ roll. At Palaia Winery in Highland Mills — known as the Hudson Valley’s “hippie” winery — you’ll find a relaxed atmosphere, with picnic areas on the grounds and a fantastic outdoor stage for live music every Friday through Sunday. Tasting fees are $5 for six wines. This year the winery is introducing some new wines to its portfolio: the “Smooth Criminal,” which is a dry red blend with a nice middle-mouth feel and a bit of spice on the finish, and a line of five varieties of mead, otherwise known as honey wine. Look for their Magical Mead and Smead Mead (Strawberry Mead). Palaia hosts many festivals throughout the year, including the Woodstock Festival on August 4 and the Grape Jam Music Festival for Maria Fareri Children’s Hospital on August 25. In September, bring the family to the Fall Festival, which includes wagon rides, pumpkin-picking, and games for the kids.  If you forget your picnic lunch, no worries — Palaia has a weekend café with light fare to pair with their wines.

Brotherhood Winery
Preserving a Legacy: Winemaker Bob Barrow and Vice President Philip Dunsmore work hard to honor Brotherhood Winery’s 179-year-old history. Photo courtesy of Brotherhood Winery.

Side Trips

Bellvale farms Creamery

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Nothing like a stop for some homemade ice cream, especially from what TripAdvisor picked as the second-best place to have homemade ice cream in the nation. Select from 25 flavors that rotate seasonally.

Orange County Distillery at Brown Barn Farms

New Hampton

Relax with an adult beverage and live music at this tasting room.

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Harness Racing Museum & Hall of Fame


At this Hudson Valley hidden gem, you’ll see artifacts relating to the greatest steeds in harness racing history, plus learn the story of harness racing, and view films and exhibits.

Clearview Vineyard
Clearview Vineyard Photo by Frank and Karen Graessi

A half-hour drive southwest will take you to Clearview Vineyard in Warwick, which was ranked No. 14 on Travel + Leisure’s list of Top 25 Vineyards All Around the U.S. Producing since 2008, Frank and Karen Graessle’s wines started out great (winning a gold award for their first wine in the amateur competition of the Hudson Valley Wine and Grape Association) and keep getting better and better. Last year, their Estate Noiret won a Double Gold Medal in the Hudson Valley Wine & Spirits Competition. Wine tastings are $8 and include six samples of wine and a 12.75-oz embossed wine glass. They also carry local draft hard cider and beer. While there, take a self-guided tour through their vineyard and hike to the top, where you’ll have a 15-mile view. So relax, take in the scenery, and sample some wine.

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