Great Pumpkin Roll Gran Fondo

September 30 2023
Brookville, IN
Date Confirmed
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Distances: 30, 45, 65 miles
Difficulty: Gently rolling terrain with one or two short hills
Limited to: 500 Participants

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!

Our event was a big hit in 2022 and featured cyclists from 12 states! Fantastic routes and amazing finish line food were a big hit and received tons of compliments. Our event will sell out in 2023.

Register early!  There is a rider limit of 500 and 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.

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
- Live Music Friday and Saturday evening at Third Place!
- bike past the beautiful Village of Spires in Oldenburg
- Strava segments
- Indiana's oldest stone bridge dating pre-civil war
- rest stop at the oldest Bar in Indiana
- covered bridge in Enochsburg
- 17 Hoosier Heritage Farms
- fabulous catered post ride meal by Third Place Tavern and Event Center
- Infinit Nutrition Hyrdation Formula at all rest stops
- make it a weekend and enjoy Brookville's Germanfest weekend and the Antique Machinery Show

Ride with GPS route maps:


Register early!  There is a rider limit of 500 and in 2023.

Great Pumpkin Roll Gran Fondo


Start Located At: 734 Main St, Brookville, IN 47012
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Day of ride details:

Registration opens at 7 am
Ride start for the 45 and 65 miles at 8:30 am
Ride start for the 25 miles at 9:30 am
post ride meal at finish line and live music from 11 – 4 pm.

Registration Fees

Ride Pricing

Early Bird until February 28   $50 ( includes ride t-shirt) 

March 1 – June 30     $55 (includes ride t-shirt) 

July 1 – August 31   $60  (includes ride t-shirt) 

September 1 – September 24    $65

Day of Registration    $70 for everyone on September 24


Stuffed rider packets
Fully stocked rest stops
Infinit Nutrition hydration at all rest stops
Event t-shirt (if registering before deadline)
Hot post ride meal!
Route GPS downloads
On route support (SAG)
Live music in the evening Friday and Saturday nights


Packet Pickups

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

Day of Packet Pickup

at Third Place Tavern and Event Center

734 Main St., Brookville, IN 47012

Saturday, September 30 @ 7 AM

Adequate Car Parking
Changing Rooms
Registration On the Day
Pre-Packet Pickups
Support for Participants
Route Signposted
First Aid
Emergency Contact No
SAG Wagon
Mechanical Support at Rest Stops
After Party
Downloadable GPS files
Finish Line Chute
Feed / Aid Stations
Post Event Meal(s) Provided As Part of Entry
Number of Aid Stations: 4
Number of Timed Hill Climbs
3 Hill Climbs