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HomeRide CalendarGreat Pumpkin Roll Gran Fondo 2023

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Great Pumpkin Roll Gran Fondo 2023

Ride Presenters



Join us for the 12th anniversary Great Pumpkin Roll Gran Fondo!

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 2022 and received tons of compliments. Our event will sell out in 2023.

In 2023 the friendly Town of Brookville will welcome us again for the 2023 Great Pumpkin Roll Gran Fondo. The ride will start and finish at Third Place Tavern and Event Center our finish line partner and host. There are three beautiful scenic Gran Fondo 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 12th annual Great Pumpkin Roll Gran Fondo which welcomes cyclists to tour the scenic routes and rural communities on September 30, 2023.

Cyclists can take part in routes ranging from 30 to 65 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 (Picolo), 47 mile (Medio) and a 60 miles Gran Fondo route.

  • cool rider packets at registration
  • Fully stocked rest stops
  • Infinit Nutrition hydration at all rest stops
  • On route support (SAG)
  • Event t-shirt (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:




Early Packet pickup

Friday, September 29, 2023 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 August 31  to score a cool Great Pumpkin Roll Gran Fondo T-shirt

Register Here 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

Photo Contest

There are so many cool things to see on our ride. Stop and take pictures and have some fun. The top 5 photo entries will win cool prizes.  Post ride send photos to to enter

Ride Pricing

Early Bird until December 31   $50 ( includes ride t-shirt) 

Jan 1 to March 5   $55 (includes ride t-shirt)

March 6 – May 31     $60 (includes ride t-shirt) 

June 1 – August 31   $65  (includes ride t-shirt) 

September 1 – September 28    $70

Day of Registration    $80 for everyone on September 30

Register Here on BikeReg

Check out these stunningly beautiful 2023 jerseys!






Saturday, September 30, 2023, 7:30 AM until 4:00 PM
Third Place
734 Main St
Brookville, IN  47012

(765) 547-1700
Club Event Rides
Registration is not Required
Payment In Full In Advance Only
Helmet is required.

Registration is required on BikeReg at