Event Date
Saturday, September 27, 2025, 8:30am
Third Place, 734 Main St., Brookville, IN 47012
Join us for the 14th anniversary Great Pumpkin Roll Ride!
This is the Brookville’s BIGGEST ANNUAL RIDE, and we roll out the orange (fall) carpet!
Check out all the pictures on Facebook from the SOLD OUT past events! We have hosted cyclists from 12 states, plus Ontario Canada and everyone loved the routes and amazing fresh finish line food made by Third Place Tavern & Event Center.
Make a weekend of it!
Cyclists can take part in routes ranging from 34 to 63 miles that begin and end at Third Place in Brookville. From the fall colors that decorate the region to the historic Village of Spires in Oldenburg, Ertel’s winery stop, and even the covered bridge in Enochsburg, we are so excited to welcome everyone to enjoy our event. Stay post ride for a super tasty freshly made hot post ride meal included in your registration!
It’s a perfect weekend getaway as it’s also Brookville’s German Fest as well as the Antique Machinery Show that weekend. The ride is fully supported with three super-stocked rest stops. After the ride, dig into a hot post ride meal included in your registration.
There are three ride distances of 34 mile, 50 mile medium and a 63 miles metric century route. Our ride features rolling scenic terrain over low traveled rural southeastern Indiana roads.
Event Proceeds benefit the Whitewater Canal Trail and the Cincinnati Cycle Club Philanthropy Foundation
Ride with GPS route maps:
34 MILE ROUTE – https://ridewithgps.com/routes/48493047
50 MILE MEDIUM ROUTE – https://ridewithgps.com/routes/48493170
63 MILE METRIC CENTURY – https://ridewithgps.com/routes/48493286
Day-of registration opens 7:00 am
The 50 and 63 mile metric century routes roll mass start at 8:30am.
The start for the 34-mile ride is at 9:30am.
Early Packet Pickup
Friday, September 26, 2025 from 6 to 8
Third Place Tavern and Event Center
734 Main St., Brookville, IN 47012
What You Get
- Great Pumpkin Roll Ride socks (if registering before September 1)
- Donuts, coffee, and Pumpkin Rolls pre-ride Saturday morning
- Stuffed rider packets
- Fully stocked rest stops
- Infinit Nutrition hydration at all rest stops
- On route support (SAG)
- Hot post ride meal!
- Ride with GPS route downloads
- Three scenic low traffic routes to choose from
- Live music in the evening Friday and Saturday nights at 7pm
Check out the super cool redesigned jerseys for 2025! Jerseys will coordinate with the event cycling socks. Order early to guarantee your jersey. 