Great Pumpkin Roll Gran Fondo

About the Event

Imagine pedaling through Southeast Indiana's vibrant fall foliage on quiet rural roads, where every turn reveals golden hills, historic bridges, and charming villages—then crossing the finish line to cheers, hearty German fare, and lively tunes. The Great Pumpkin Roll Gran Fondo is Brookville's biggest annual cycling celebration, a one-of-a-kind gran fondo blending challenging rides with festive community spirit on September 26, 2026. What makes it special? Three scenic routes (34, 50, or 63 miles) showcase rolling terrain perfect for all levels, fully supported with stocked rest stops, SAG wagons, and perks like pumpkin rolls, donuts, and a hot post-ride meal. Riders from across states and beyond flock here for the camaraderie, stunning autumn views, and the unbeatable finish at Third Place during Germanfest Weekend—pure joy on two wheels that leaves you energized and eager for more. ## The Surrounding Area
Nestled in Franklin County, Brookville is a hidden gem of small-town charm in Southeast Indiana, where the Whitewater River winds through hills dotted with historic sites and lush forests. Known as the "Village of Spires" nearby in Oldenburg, this area boasts over 30 steeples piercing the sky, a testament to its rich German Catholic heritage. Visitors love the Enochsburg covered bridge, a picturesque 19th-century icon perfect for photos, and nearby attractions like the Whitewater Canal State Historic Site with its canal boats and pioneer history. Dining shines at Third Place Tavern & Event Center, serving up fresh, flavorful meals, while Germanfest brings bratwurst, pretzels, and brews. Extend your stay for the Antique Machinery Show—steam engines chugging amid harvest vibes. It's an inviting escape blending outdoor adventure, heritage, and warm Midwestern hospitality that makes every visitor feel like family. ## Activities & Attractions
This gran fondo packs adventure and festivity into one unforgettable day:

• Scenic Cycling Routes: Choose your challenge—34 miles for a relaxed spin, 50 miles for steady rolling hills, or 63-mile metric century for epic vistas. All wind through low-traffic roads highlighting fall colors, Oldenburg's spires, Ertel’s Winery stop, and Enochsburg's covered bridge.
• Pre-Ride Fuel: Donuts, coffee, and signature pumpkin rolls to kick off your ride.
• On-Course Support: Three fully stocked rest stops with Infinit Nutrition hydration, plus SAG support for peace of mind.
• Finish Line Feast: A hot, freshly made meal awaits every rider, paired with the Germanfest Weekend vibes—think German food, local drinks, and endless cheer.
• Germanfest Integration: Dive into authentic eats, beers, and cultural fun right at Third Place.
• Live Music: Catch performances Friday and Saturday evenings at 7pm, with dancing under the stars.
• Rider Swag: Exclusive socks (early birds), stuffed packets, Ride with GPS maps, and optional redesigned jerseys.
  Tie it all together with the Antique Machinery Show nearby for a full weekend of wholesome excitement. ## Schedule & Logistics
  Mark your calendar for Saturday, September 26, 2026, at Third Place, 734 Main St., Brookville, IN 47012—day-of registration opens at 7:00am. The 50- and 63-mile routes mass start at 8:30am, with the 34-mile ride rolling out at 9:30am. Prep ahead with early packet pickup on Friday, September 25, from 6-8pm at the same spot. Parking is ample at Third Place; rides are fully supported, so focus on the fun. Admission is via registration (limited to 500 riders—book early!), including all meals, swag, and support. Expect a seamless day ending with evening live music—easy logistics for a stress-free adventure. ## History & Heritage
  Launched over a decade ago, the Great Pumpkin Roll Ride hits its 15th anniversary in 2026, evolving from a local cycling gem into Brookville's premier annual event, drawing riders from 12 states and Canada. Founded by passionate locals tied to the Cincinnati Cycle Club, it celebrates Southeast Indiana's rural beauty while supporting the Whitewater Canal Trail and philanthropy foundations—pumping proceeds back into community trails. What started as a fall foliage spin has grown into a sold-out tradition, blending gran fondo rigor with Germanfest heritage, fostering rider bonds and boosting Brookville's spirit. It's more than a ride; it's a heartfelt tribute to the area's cycling culture and pioneer past, growing stronger each year with fresh routes and festive flair.