Breaking Away Trail, Morgan-Monroe State Forest

The Hilly Hundred Loop offers a challenging road cycling adventure through southern Indiana's picturesque rural landscape. You'll navigate rolling country roads, passing through charming settlements and alongside dense woods, with the terrain constantly shifting between steep climbs and exhilarating descents. The route is particularly stunning in early October, when the fall foliage around places like Mt. Tabor creates a vibrant backdrop for your ride.

This difficult 64.1-mile (103.2 km) loop, with its substantial 2657 feet (810 metres) of elevation gain, typically takes around 5 hours and 25 minutes to complete. While it's famous as an organized event, you can tackle it independently. Plan your ride for early October to experience the most vibrant autumn colors, and be prepared for a demanding workout that requires strong climbing ability.

Beyond its challenging hills and beautiful scenery, the Hilly Hundred is nationally recognized as one of the "Best Rides in America." Founded in 1968, it's one of Indiana's longest-running cycling events, attracting thousands of riders annually. Even when ridden solo, the route carries the legacy of this festive atmosphere and its reputation as a significant test for cyclists.

If you're after a road cycling adventure that truly tests your legs, the State Forest loop delivers with its varied terrain and scenic rewards. This moderate 49.9-mile (80.3 km) route winds through the tranquil wooded areas and mixed hardwood forests of the Morgan-Monroe State Forest, offering a journey across rolling hills and steep ridges. You'll encounter both well-paved sections and some unpaved or loose gravel segments, making it a dynamic ride that keeps you engaged for its typical duration of 4 hours and 1 minutes.

Planning your ride means being ready for a significant challenge, as the loop includes 2070 feet (631 metres) of elevation gain. While much of the route is on paved roads, a suitable racebike is recommended to handle any unpaved sections. The historic town of Ellettsville provides a convenient stop for refreshments, and the fall season is particularly recommended for its stunning foliage.

One of the unique aspects of this loop is the inclusion of the Morgan Monroe Hike-Bike Trail, also known as the "Breaking Away Trail." This 5-mile paved section adds a touch of cinematic history, named after the 1979 movie *Breaking Away* which centered on the Little 500 bicycle race at Indiana University. It's a route that combines natural beauty, a good workout, and a nod to cycling culture.