Handcrafted Octoberfest at Rhinebeck: A Family Harvest Celebration

Get ready for an unforgettable fall weekend as Handcrafted Octoberfest: A Family Harvest Celebration returns to the Dutchess County Fairgrounds in Rhinebeck! Now in its sixth year, this one-of-a-kind festival blends the best of Oktoberfest traditions with the charm of a juried craft show—perfect for art lovers, families, and everyone in between.

Promoted by Quail Hollow Events, a nationally recognized craft promotion company with decades of experience, Handcrafted Octoberfest is a two-day juried show held in charming Rhinebeck, NY, a historically significant and hip destination in the heart of the Hudson Valley, known for its classic fairgrounds, picturesque Market Street, and vibrant creative community. This festival reimagines the traditional Oktoberfest through an artistic lens, celebrating the spirit of the season by highlighting all things handmade.

Launched in 2019, the event quickly earned a reputation as a fall favorite, drawing thousands of visitors each year and becoming a seasonal highlight in the booming Hudson Valley, now widely recognized as an artistic hotspot. With over 100 juried exhibitors showcasing work across ten media categories, the festival brings together the handcrafted, the artisanal, and the agricultural, from fine art and crafts to craft brews, regional wine and spirits, specialty foods, and abundant harvest fun.

Visitors can sip, eat and unwind in the beer garden and entertainment tent, and enjoy an eclectic lineup of live entertainment throughout the weekend. On Saturday, don’t miss The Lucky Losers, a San Francisco-based touring duo whose award-winning blend of blues, soul, and American roots delivers a high-energy, vintage-tinged set full of chemistry and heart. Fronted by dynamic vocalists Cathy Lemons and Phil Berkowitz, they’ve been hailed as one of the best blues acts touring today, known for their retro sounds and storytelling.

Sunday brings the return of Roadhouse, a lively 1960s cover band beloved throughout the region. Featuring Tom, Steve, Mike, and Richie, Roadhouse delivers a nostalgic and danceable set packed with your favorite top ten hits—perfect for grooving, singing along, or just soaking up the good vibes after shopping rows of one-of-a-kind handmade goods.

Returning for the second year is Witches Along the Hudson, a joyful and spirited dance troupe dedicated to fundraising for the Greene County Animal Alliance. The all-volunteer dance group hopes to open a much-needed animal shelter in the region. Their uplifting, witchy and fun performances are impossible to miss, and add a touch of playful magic to the festival. Don’t forget to stop by their booth to shop handmade brooms and learn more about their cause.

Families will love the dedicated kids’ craft tent, where children can paint pumpkins, engage in artistic free play, or complete a seasonal art project.

Around the fairgrounds, guests will enjoy ongoing demos from woodworkers, fiber spinners, leathersmiths, jewelers, and even a master pumpkin carver. For even more fall magic, visitors can hop on a horse-drawn carriage ride, visit the petting zoo, or witness the weigh-off of giant pumpkins!