Great Pumpkin Roll Ride 2026

Experience the 15th anniversary of the Great Pumpkin Roll Ride on September 26, 2026. This annual cycling extravaganza is Brookville's biggest celebration and promises an unforgettable journey through the picturesque fall landscapes.
Cyclists can choose from three exciting routes: a scenic 34-mile ride starting at Third Place in Brookville, a challenging 50-mile medium route, or the metric century 63.6-mile challenge that will take you on a memorable adventure through time and nature.
The ride offers fully supported rest stops with plenty of refreshments, including Infinit Nutrition hydration stations to keep you fueled throughout your journey. On-route support ensures that every cyclist is well taken care of, while GPS route maps are available for download before the event or during pre-ride preparations at Third Place Tavern & Event Center.
Start your adventure early with a pre-ride breakfast from Schmidt Bakery in Batesville, featuring fresh pumpkin rolls and complimentary coffee and juice. The ride concludes with a delicious post-ride meal prepared by the talented chefs at Third Place Tavern & Event Center, included in registration fees.
Explore the charming Village of Spires in Oldenburg, visit Ertel's winery for a taste of local flavors, or marvel at the historic covered bridge in Enochsburg. The event also coincides with Brookville’s German Fest and Antique Machinery Show, making it an ideal weekend getaway to experience both cultural festivities.
Register early to secure your spot at one of these prices: $55 for earlybird registration (March 30 - June 29), $60 from July 1 - August 30, or $75 on the day of the event. Last chance to pre-order a custom jersey is July 20, 2026.
Proceeds from this year's ride will benefit the Whitewater Canal Trail, TRAM Food Pantry, and Cincinnati Cycle Club Philanthropy Foundation.
Join us for an event that combines breathtaking scenery with community spirit and friendly competition. Whether you're a seasoned cyclist or just starting out, there’s something here to challenge and inspire you.