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!

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

Date: September 27, 2025
Distances: 34, 50, 63 miles
City, State: Brookville, Indiana
Start Location: Third Place, 734 Main St
Start Time: 8:30 am
Online Information: https://greatpumpkinrollride.com/
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