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Routes
Road cycling routes
United States
Indiana
Monroe County
Ellettsville

Hilly Hundred Loop

Hard

4.7

(8400)

8,401

riders

Hilly Hundred Loop

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

A

Start point

Parking

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1

59.6 km

Breaking Away Trail, Morgan-Monroe State Forest

Highlight (Segment) • Trail

Affectionately referred to as the “Breaking Away Trail” based on the 1979 movie about the Little 500 bicycle race held annually at Indiana University. The 5 mile long paved trail …

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2

102 km

Ellettsville

Highlight • Settlement

Founded in 1837 Ellettsville is a historic town 7 miles west of Bloomington. Along with its historic buildings it's a great place to stop for a cup of coffee or something to eat on your ride.

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103 km

End point

Parking

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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 %

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Max wind speed: 14.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the Hilly Hundred Loop?

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.

What is the terrain like on this route?

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.

Is the Hilly Hundred Loop suitable for beginners?

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.

What is the best time of year to cycle this route?

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.

Where can I park for the Hilly Hundred event?

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.

Are there any permits or entrance fees required to cycle the Hilly Hundred Loop?

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.

Is the Hilly Hundred Loop dog-friendly?

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.

What can I see along the route?

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.

Does the route intersect other well-known paths?

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.

What makes the Hilly Hundred event unique?

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.

What should I bring for a ride on the Hilly Hundred Loop?

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.

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