Join us for the 15th anniversary Great Pumpkin Roll Ride! This is the Brookville's BIGGEST ANNUAL RIDE, and we roll out the orange (fall) carpet!
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.
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.
What You Get
- Great Pumpkin Roll Ride socks (if registering before September 24)
- 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!
- Live music in the evening Friday and Saturday nights at 7pm
Date: September 26, 2026
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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