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.

There are easier foods to build a guide around. Pizza has categories. Tacos have categories. Coffee shops have categories. Burgers are chaos. Some are smashed paper-thin with crispy edges. Some are thick enough to require a strategy before the first bite. Some come loaded with ingredients that barely fit between the bun. Others rely on nothing more than great beef, melted cheese, and confidence.

The Hudson Valley has no shortage of places to get a cup of coffee. What it has, if you know where to look, is a handful of shops doing something worth going out of your way for. Not just good espresso, but places with a point of view, a reason they exist, and a room that makes you want to stay longer than you planned.

Two stamps down, appetite wide open. At Harvest on Hudson and Half Moon, dinner isn’t merely plated — it’s charted, stamped, and story-driven. Your Passport becomes the thread that ties each journey together: every evening earns a mark, every dish becomes a memory, and every return visit unlocks a new layer of the adventure.

Every fall, when the harvest moon rises high and the nights start to cool, millions gather around the world to honor one of Asia’s oldest...

Hudson NY's Swoon Kitchenbar, Hudson Valley’s first farm-to-plate restaurant, is celebrating 20 years in business.