Do you like wine? How about horses? If you answered yes to either of those questions, then the Penns Woods' Derby at the Vineyard events are calling your name!  

The vineyard’s annual Derby Day celebrations commence  on May 20th and 21st from 10:00 a.m. - 6:00 p.m. Enjoy the festivities of a Hunter Derby mixed with beautiful views of the Penns Woods grounds and their award-winning wines to top off your experience. What exactly is a Hunter Derby you may be asking... A Hunter Derby is a two-round horse jumping competition in which both rounds include natural fences reminiscent of the hunt field, such as stone walls, logs, brush jumps, white board fences, post-and-rail jumps, gates or coops. 

Enjoy this spectacular horse jumping event in the vineyard with wine, local beer & cider, live music all day long, food trucks, and artisan vendors, plus a chance for the kids to get up close to the stars of the show at the meet & greet station! Kick off the morning with brunchy bites from local food trucks & enjoy bottomless mimosas from 10 a.m. - noon. Attendees are also encouraged to put on their best derby day attire (think big hats & bright colors!) for a chance to win prizes for "Best Dressed.  

Music Line Up 


11:00-2:00 p.m.: Paul Wilkinson and 2:30 - 5:30 .p.m: Greg Jones 


11:00 - 2:00 p.m.: Bill Hake and 2:30 - 5:30 p.m.: Jason Ager 

Food Trucks


8:30 - 3:00 p.m.: Waffle 'n Joe and 10:00 - 5:00 p.m.: The Grateful Gourmet, On the Roll 


8:30 - 11:00 a.m.: Cinnamon Bun Exchange and 10:00 - 5:00 p.m.: The Grateful Gourmet, On the Roll 

Local Vendors 

11:00 - 4:00 p.m.: Northern Belle Hat Co., Sow & Sew Boutique, Traditional Greek Sweets, The Minimalist Boutique, Urban Essence Salon & Spa, The D3lco Efect, KC Esstentials, Love Leigh Craft Co. 

Penns Woods Winery

Penns Woods' acclaimed wines are the star of the show but they're not the only reason to visit. The winery is a local favorite for fun events…

If you can’t make Derby Weekend, be sure to check out the Penns Woods other events or book yourself a tasting with friends! Learn more at