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Road cycling routes
United States
Indiana
Monroe County
Bloomington

Bloomington to Harrodsburg loop

Moderate

4.9

(5520)

15,155

riders

Bloomington to Harrodsburg loop

02:28

51.5km

420m

Road cycling

This moderate 32.0 miles (51.5 km) road cycling loop from Bloomington to Harrodsburg features rolling hills and historic districts.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

28.1 km

Harrodsburg Historic District

Highlight • Historical Site

Harrodsburg is a small southern Indiana town of 656 people. It has a Historic District with a number of buildings from the 1800's including the post office which has been in operation since 1840.

Tip by

2

51.3 km

Bloomington Courthouse Square

Highlight • Historical Site

Centered around the Monroe County Courthouse, the Square is downtown Bloomington's most popular areas. With numerous eateries and cafes, it's a great place to start, end, or or pass through on a ride.

Tip by

B

51.5 km

End point

Parking

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Way Types & Surfaces

Way Types

40.5 km

8.74 km

1.79 km

444 m

Surfaces

29.4 km

22.1 km

< 100 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 (280 m)

Lowest point (150 m)

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Weather

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Today

Wednesday 15 July

33°C

21°C

12 %

Additional weather tips

Max wind speed: 7.0 km/h

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Frequently Asked Questions

What is the terrain like on the Bloomington to Harrodsburg loop?

The terrain on this loop is characterized by challenging rolling hills, ridges, and ravines, often featuring 'mean little climbs.' It's a demanding ride, comparable to hilly areas in North Carolina or Georgia, requiring good fitness. Expect significant elevation changes, especially when leaving Bloomington.

Is the Bloomington to Harrodsburg loop suitable for beginners?

Given its 'moderate' difficulty and the presence of challenging rolling hills and steep climbs, this loop is generally not recommended for beginners. Cyclists should have good fitness and experience with varied terrain to comfortably enjoy this route.

What can I see along the route?

The loop offers scenic views of wooded areas, fields, and farm life. You'll pass through the historic town of Harrodsburg, where you can explore the Harrodsburg Historic District. In Bloomington, the route is near the Bloomington Courthouse Square. You may also catch glimpses of limestone quarries and unique farm animals.

Where can I park to access the loop?

While specific parking for this exact loop isn't detailed, Bloomington is a cycling hub with various public parking options. For general cycling access in Bloomington, you can find public parking downtown or near parks that connect to local trail systems. Check local resources like Visit Bloomington for up-to-date parking information.

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

The best time to cycle this loop is typically during spring and fall when temperatures are milder. Summer can be enjoyable, but be prepared for warmer conditions. The area's challenging topography means you'll want to avoid icy conditions in winter.

Is the Bloomington to Harrodsburg loop dog-friendly?

This route is primarily a road cycling loop. While dogs are generally not suitable for being on a racebike with you, if you plan to stop at parks or natural areas along the way, check specific regulations for those locations regarding dogs. Always keep dogs on a leash where permitted.

Do I need a permit or pay any entrance fees for this route?

No, there are no specific permits or entrance fees required to cycle the public roads that make up the Bloomington to Harrodsburg loop. However, if you venture into state parks or forests nearby, separate fees or permits might apply for those specific areas.

Does the loop intersect other well-known paths?

Yes, the route passes through sections of several local paths, including the B-Line Trail, Bloomington Rail Trail, and Limestone Greenway. You may also encounter parts of the Clear Creek Trail and the 7th Street Greenway.

Are there any cafes or amenities along the route?

Bloomington, being a larger town, offers numerous cafes, restaurants, and amenities. Harrodsburg is a smaller community, but you may find local establishments there. It's advisable to carry sufficient water and snacks, especially for the more rural sections between the towns.

What should I know about the elevation profile of the loop?

The loop features a total elevation gain of approximately 418 meters. You should expect a ride with frequent ups and downs, as the area is known for its 'rolling hills' and 'hard-earned climbs.' Be prepared for some steep sections, particularly when starting or returning to Bloomington, which is situated on a ridge.

Is there a strategic way to approach the climbs on this route?

Given that leaving Bloomington generally involves steep climbs, consider your starting direction. If you prefer to tackle the most significant ascents early, starting from Bloomington and heading out might suit you. Alternatively, if you prefer a more gradual warm-up, plan your route accordingly, but be aware that challenging climbs are inherent to the area's topography regardless of direction.

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