Community Spotlights

Rhinebeck is full of annual events and special celebrations. Please visit the respective websites of these fine events for dates and more information. Some highlights include these top attractions – please visit our Chamber Calendar or Community Calendar pages for more.
photo of ferris wheel at Dutchess County Fair

Photo: Maureen Gates

The Dutchess County Fair

Every third week in August the fairgrounds celebrate its premier event, the Dutchess County Fair – the second largest agricultural fair in New York. With rides, arts, crafts, arcades, family-fun, food galore, and so much more, it is the beloved destination for visitors from all over the country. The fairgrounds present other flagship events, including the NYS Sheep & Wool Family Festival, Country Living Fair and an array of other exciting festivals and special events. The site can see crowds of over half-million people yearly.

photo of ballons at Dutchess County Balloonfest

Hudson Valley Hot-Air Balloon Festival

This eye-popping event hosts balloonists and vendors from all over the country at select locations in Dutchess County each summer. A Hudson Valley tradition, it has grown into a full weekend of activities, including vendors, rides, games and more, drawing tens of thousands of visitors from all over the world. Festival favorites include evening moon-glow illuminations, tethered rides, and traditional rides throughout the weekend. Also find helicopter rides, hayrides, live music, and family activities. Each July.

Hudson Valley Wine Festival Wine Servers

The Hudson Valley Wine & Food Festival

The Hudson Valley Wine & Food Festival celebrates the bounty of wine, food and fun in the heart of Rhinebeck. Get ready to experience hundreds of wineries, cideries, distilleries, craft beers, food trucks, gourmet foods, seminars and more. A spectacular variety of vendors from far and wide appear for this vibrant event. Held each September, the weekend after Labor Day.

photo of lamb and two ewes

Sheep and Wool Family Festival

The New York State Sheep and Wool Festival is one of the largest annual gatherings of fiber-arts enthusiasts in the United States. Held at the Dutchess County Fairgrounds, it is attended by the masses from all over the country. A highly popular and celebrated event for the entire family, the festival boats live animals, workshops, demos, activities, talks, supplies and, of course, shopping. Always the third weekend in October.

photo of Sinterklaas celebration


The tradition of Sinterklaas comes all the way from the Netherlands, brought by Dutch settlers who arrived in Rhinebeck over 300 years ago. Sinterklaas, the patron of children and sailors, finds a welcoming community in the Mid-Hudson Valley as the event re-creates the story through the lens of modern-day America. This is a spirited family event featuring live music, street fare, abundant costumes and a parade. Always the first Saturday in December in the center of Rhinebeck village.