Join us for the 14th anniversary Great Pumpkin Roll Ride!
This is the Queen City’s BIGGEST ANNUAL RIDE and we roll out the orange (fall) carpet!
Last year's event featured cyclists from 12 states! Fantastic routes and amazing finish line food were a big hit.
In 2025 the friendly Town of Brookville will welcome us again for the 2025 Great Pumpkin Roll Ride. The ride will start and finish at Third Place Tavern and Event Center our finish line partner and host. There are three beautiful scenic routes and lots of sights to see and many photo opportunities. Make sure to enter the ride photo contest! Stay post ride for a super tasty hot post ride meal included in your registration!
Make a weekend of it!
Third Place and Whitewater Publications has teamed up with the Cincinnati Cycle Club to host the 14th annual Great Pumpkin Roll Ride which welcomes cyclists to tour the scenic routes and rural communities on September 27, 2025.
Cyclists can take part in routes ranging from 30 to 63 miles that begin and end at Third Place in Brookville.
The ride will go through the St. Mary's, into Oldenburg, through Enochsburg, past Ertel's Winery and into St. Peters before returning to Brookville.
It's a perfect weekend getaway as it's also Brookville's Germanfest 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.
Our ride features rolling scenic terrain over low traveled rural southeastern Indiana roads.
There are three ride distances of 30 mile, 50 mile, and a 63 mile metric century route.
- cool rider packets at registration
- Fully stocked rest stops
- Infinit Nutrition hydration at all rest stops
- On route support (SAG)
- Event cycling socks (if registering before September 1)
- Fabulous catered post ride meal by Third Place Tavern and Event Center
- Ride with GPS route downloads
- Three fantastic routes in 2023
- Strava Segments
- Live music in the evening Friday and Saturday evening.
- bike through the beautiful Village of Spires in Oldenburg
- rest stop at the oldest Bar in Indiana
- covered bridge in Enochsburg
- make it a weekend and enjoy Brookville’s Germanfest weekend and the Antique Machinery Show
Event Proceeds benefit the Whitewater Canal Trail and the Cincinnati Cycle Club Philanthropy Foundation
Register early! There is a rider limit of 500 and in 2023 and we anticipate a sellout.
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
Early Packet pickup
Friday, September 26, 2025 from 6 to 8 pm
at Third Place Tavern and Event Center
734 Main St., Brookville, IN 47012
All registrations include fully stocked rest stops, SAG, route markings and maps and a wonderful post ride meal.
Register by Aug 31st to get your FREE Great Pumpkin Roll Ride socks!
Register on BikeReg
Day of ride details:
Registration and packet pickup opens at 7 am
Ride start for the 45 and 65 miles at 8:30 am
Ride start for the 30 miles at 9:30 am
post ride meal at finish line from 11 – 4 pm.
Live music at 7pm
Ride Pricing
Early Bird until March 31 $55 (includes Great Pumpkin Roll Ride cycling Socks)
March 31 - June 30 $60 (includes Great Pumpkin Roll Ride cycling Socks)
July 1 – August 31 $70 (includes Great Pumpkin Roll Ride cycling Socks)
September 1 – September 26 $75
Day of Registration $85
Check out these stunningly beautiful 2025 jerseys!
