Great Pumpkin Roll Gran Fondo

The Great Pumpkin Roll Gran Fondo is an annual cycling event held in Brookville, Indiana, featuring scenic rolling terrain on rural roads in southeastern Indiana. The 2025 event takes place on Saturday, September 27, starting and finishing at the Third Place Tavern and Event Center (734 Main St, Brookville, IN). It offers three route options: a 34-mile ride starting at 9:30 a.m., a 50-mile medium route, and a 63-mile metric century route that start together at 8:30 a.m. The event benefits the Whitewater Canal Trail and the Cincinnati Cycle Club Philanthropy Foundation.

The vibe of the event is community-focused and festive, with a post-ride celebration at Third Place Tavern during their Germanfest Weekend, featuring German food, drinks, and live music. There is live music on both Friday and Saturday evenings at 7 p.m., creating a fun and lively atmosphere.

Activities and features include:

• Three scenic cycling routes on low-traffic rural roads (34, 50, 63 miles).
• Early packet pickup on Friday, September 26, from 6 to 8 p.m. at Third Place Tavern.
• Day-of registration opens at 7 a.m.
• Pre-ride refreshments including donuts, coffee, and pumpkin rolls on Saturday morning.
• Rider packets including Great Pumpkin Roll socks (if registered before September 1).
• Fully stocked rest stops with hydration (Infinit Nutrition) and support vehicles.
• Hot post-ride meal at finish line.
• Live music on Friday and Saturday evenings starting at 7 p.m.
• Opportunity to purchase coordinating event jerseys.

Typical event schedule:

• Friday, September 26: Early packet pickup, 6–8 p.m. at Third Place Tavern, live music at 7 p.m.
• Saturday, September 27: Day-of registration from 7 a.m.; 50 and 63-mile rides mass start at 8:30 a.m.; 34-mile ride starts at 9:30 a.m.; refreshments before ride; fully supported rest stops; ride finishes at Third Place Tavern for Germanfest food, drinks, and music.

The event is in its 14th year as of 2025 and is known as Brookville’s biggest annual ride, embracing the fall pumpkin theme and rural Indiana scenery. It emphasizes camaraderie, charitable benefit, and a festive post-ride atmosphere.

The location, Third Place Tavern, is notable as both start and finish line and hosts the Germanfest Weekend concurrently with the ride, adding an additional cultural and celebration element to the event. The area is rural southeastern Indiana with scenic rolling roads, making the ride enjoyable yet challenging.

The event is accessible (handicapped accessible) and requires an admission fee. Contact information is provided via phone and website, and the event actively promotes cycling community support and philanthropy.