The Hudson Valley Wine & Food Festival is not a quick lap around a few tasting tables. It is a full weekend in Rhinebeck built for people who want to discover what is actually in the glass, meet the people behind it, and leave with a new bottle obsession.

Fifty-two September 2026 events North of NYC throughout the Hudson Valley and beyond—from balloons and jazz to wine, art, garlic and giant pumpkins.

One lucky winner will receive the ultimate Westchester getaway, valued at more than $1,700, including a two-night stay at Sonesta White Plains Downtown, four tickets to Caramoor with a private Rosen House tour, four tickets to the Pleasantville Music Festival to see Ok Go, Old 97's, The Fixx, Yola, and more live, dinner for two at Freebird Kitchen & Bar, and dinner for two at Hudson Grille.