4.7
(8400)
8,401
riders
05:25
103km
810m
Road cycling
Prepare for a challenging road cycling adventure on the Hilly Hundred Loop, a difficult route spanning 64.1 miles (103.2 km) with a significant 2657 feet (810 metres) of elevation gain. This ride, estimated to take around 5 hours and 25 minutes, winds through rolling country roads in the rural landscapes…
Last updated: April 23, 2026
Waypoints
Start point
Parking
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59.6 km
Highlight (Segment) • Trail
Tip by
102 km
Highlight • Settlement
Tip by
103 km
End point
Parking
Way Types & Surfaces
Way Types
60.4 km
29.1 km
13.6 km
130 m
123 m
Surfaces
70.7 km
31.9 km
600 m
123 m
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Elevation
Highest point (270 m)
Lowest point (170 m)
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Weather
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Today
Thursday 7 May
17°C
2°C
0 %
Additional weather tips
Max wind speed: 14.0 km/h
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This route was planned by komoot.
The Hilly Hundred Loop is a renowned two-day, non-competitive bicycle tour in south-central Indiana, primarily traversing Monroe, Owen, and Morgan counties. It's a significant event for road cyclists, attracting thousands of participants annually, known for its challenging terrain and picturesque fall scenery.
As the name suggests, the terrain is notably hilly, featuring rolling country roads with both steep climbs and descents. Over the course of the approximately 100 miles (split into two 50-mile days during the event), cyclists can expect to climb over 5,600 feet of elevation. The routes generally utilize scenic back roads, avoiding busy state highways.
While the route is considered 'difficult' with significant elevation gain, the Hilly Hundred event is designed for touring bicyclists of varying abilities, not just racers. Each day offers multiple route options, including shorter 30-plus-mile alternatives, to accommodate different fitness levels. Riders are advised to pace themselves due to the steep, though not necessarily long, hills.
The Hilly Hundred event typically takes place in early October, which is celebrated for its picturesque scenery, showcasing the vibrant fall foliage of southern Indiana. This makes early autumn an ideal time to experience the route's natural beauty.
For the official Hilly Hundred event, parking arrangements are typically organized by the Central Indiana Bicycling Association (CIBA). Key locations like Ellettsville are often central to the event's logistics, including parking. Specific details are usually provided closer to the event date by the organizers.
If you are participating in the official Hilly Hundred event, there is a registration fee to cover event support, food, and amenities. If you are cycling the route independently outside of the event, there are no specific permits or entrance fees required as it primarily uses public roads. However, a small portion of the route passes through Morgan-Monroe State Forest, which may have its own regulations or entrance fees for vehicles, though cycling through is generally unrestricted.
Given that the Hilly Hundred is a road cycling event on public roads, it is generally not suitable for dogs to accompany cyclists on the route, especially during the organized event with thousands of participants. If you are cycling the route independently, dogs are typically allowed in public areas and on roads, but always ensure they are leashed and that you adhere to local regulations, particularly within areas like Morgan-Monroe State Forest.
The route is celebrated for its picturesque rural landscapes and vibrant fall foliage. Notable points include sections within Morgan-Monroe State Forest, and the town of Ellettsville. The event is also known for its festive atmosphere, camaraderie, and live music at rest stops.
Yes, the route briefly intersects with or runs alongside several other paths. These include small sections of the Three Lakes Trail, Heritage Trail, and the Morgan-Monroe Hike Bike Trail.
Beyond the cycling challenge, the Hilly Hundred is known for its festive atmosphere, camaraderie, and comprehensive support. Rest stops along the routes offer free food, drinks, and live music. The tour is fully SAG (Support and Gear)-supported, with mechanics available at rest stops for unexpected repairs, ensuring a well-organized and enjoyable experience. It's one of Indiana's longest-running and most popular cycling events.
For this challenging route, especially if cycling independently, you should bring a well-maintained road bike, appropriate cycling attire, a helmet, plenty of water and snacks, a repair kit (spare tube, pump, tire levers), and navigation tools. If participating in the event, many amenities are provided, but personal essentials remain important.