1 cycling event in Brookville, Indiana

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Ride Presented by

Cincinnati Cycle Club Foundation

Join us for the 15th anniversary Great Pumpkin Roll Ride on September 26, 2026

This is the Brookville’s BIGGEST ANNUAL RIDE, and we roll out the orange (fall) carpet!

In 2025 We hosted cyclists from 12 states, plus Ontario Canada and everyone loved the routes and amazing fresh homemade finish line food made by Third Place Tavern & Event Center.

Make a weekend of it!

Cyclists can take part in routes ranging from 30 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 30 mile, 50 miles, and a 63-mile metric route.

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• free Great Pumpkin Roll Ride cycling socks for registered participants.

• cool rider packets at registration

• Fully stocked rest stops

• Infinit Nutrition hydration at all rest stops

• On route support (SAG)

• Ride with GPS route downloads

• Pre-ride fresh pumpkin rolls from Schmidt Bakery in Batesville, coffee, and juice

• Fabulous hot freshly made catered post ride meal by Third Place Tavern and Event Center

• bike through the beautiful Village of Spires in Oldenburg

• pedal past 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, TRAM Food Pantry, and the Cincinnati Cycle Club Philanthropy Foundation

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Ride with GPS route maps:

34.7 Mile Route – https://ridewithgps.com/routes/48493047

50 Mile Medium Route – https://ridewithgps.com/routes/48493170

63.6 Mile Metric Century Route – 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 25, 2026 from 6 to 8 pm

Third Place Tavern and Event Center

734 Main St., Brookville, IN 47012

Ride Pricing

Earlybird registration $55

March 30 - June 29 $60

June 30 – August 30 $70

August 31 – September 26 $75

Day of Registration $85

We will design new super cool new Great Pumpkin Roll Ride jerseys for 2026! Last day to pre-order a jersey is July 20, 2026. (2025 jersey shown)

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Some Fun Pictures from a previous ride!

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Thank you to our wonderful ride sponsors.

Platinum Sponsor

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Gold Sponsors

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Bronze Sponsors

Cincy Builders Services LLC