Festivals and Events


Olde Rhinebeck Inn

Despite the fact we are in the country, there is a lot going on out there, it would be impossible to offer a fully comprehensive list, so here are some of the biggies, please consult Dutchess Tourism and Ulster Almanac offerings closer to your travel dates.

May 3, 2019 – May 5, 2019

Rhinebeck Antique Car Show & Swap Meet

Dutchess County Fairgrounds
Swap meet, hot rods, antique and custom car show

Dutchess County Fairgrounds

May 31, 2019 – June 2, 2019

Country Living Fair at The Dutchess County Fairgrounds

Country Living magazine style come to life! Antiques, Artisans, Home, Garden, Specialty Foods and more!

June 22, 2019 – June 23, 2019

Rhinebeck Crafts Festival

Thoughtfully curated celebration of all things handmade, featuring 200 Ameirican makers.

June 29 – August 18, 2019


Bard SummerScape festival features 7 weeks of world-class opera, theater, dance, cabaret, film, and music, including the 30th annual Bard Music Festival.

July 12, 2019 – July 14, 2019

28th Annual Hudson Valley Hot Air Balloon Festival

A 100 colorful balloons launched over Rhinebeck, balloon rides, spectacular Moon glow, live music and family activities

August 20, 2019 – August 25, 2019

174th Dutchess County Fair

Farm animals, horticultural exhibits, rides, concerts, food and fun

The 20th Annual Ramble will take place on August 31, September 1, 7-8, 14-15, 21-22, and 28-29 of 2019!

Hudson Valley Ramble

Walk,Hike, Bike, Paddle celebrate the rich natural resources, landscapes and communities and trails throughtout the region.

September 7, 2019 – September 8, 2019

Hudson Valley Wine & Food Festival

Wineries, Cideries, Distilleries, Craft Beers, Food Trucks and Gourmet Foods.

This festival brings together the handcrafted, artisanal and agricultural with a abundance of harvest attractions, beer and German specialties.

October 12, 2019 – October 13, 2019

Barn Star Antiques at Rhinebeck

Showcasing 120 + exhibitors a high quality and sophisticated presentation of antiques of many styles and periods.

October 19, 2019 – October 20, 2019

NYS Sheep & Wool Family Festival

Anything and everything that has to do with the fiber arts, yarn, and handmade items, workshops, demos, livestock.

Be preparred to partake in a Pickle eating or pickle toss contest, 100 vendors, crafts and food

Saturday, December 7, 2019

Sinterklaas Festival Day, Rhinebeck, New York

One of a kind magical holiday tradition, musical performances, children’s Illuminated evening parade.

"Rhinebeck is a terrific area with rich deep history, great eateries, galleries, assorted shops, and antiques emporiums, awesome estates up and down river."
"It is well-located if you want to tour the Hudson River Valley area, near many of the major sites. "
Book Now - Olde Rhinebeck Inn