Scott County, IL Gravel Loop

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Winchester, Illinois
Date Published:
June 15, 2022
Gravel Ratio:
55% G / 45% P
Difficulty Rating:
Enjoyability Rating:
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This route is brought to you by Anne Schroll one of our 2022 Route Ambassadors and gravel biking enthusiast from Springfield, Illinois.
Photo Credits: Anne Schroll


This is a really nice ride that starts from Rural Cyclery Bike Shop in Winchester, Illinois and rolls south out of town. The first few miles are mostly downhill as you work your way into the Illinois river bottoms, where the route winds through pancake flat farmland before crossing under Interstate 72 via a tunnel. (There’s a healthy population of cliff swallows living in the tunnel that will swoop down and seem to be chasing you, but not to worry – they are only after insects stirred up by cyclists.)

At mile 30, you leave the river bottoms and have a short but punchy climb up to the top of the bluffs. The terrain changes from farmground to mostly forests and fields and presents some incredible views.

Rattlesnake Hollow Road at mile 32 is particularly scenic and has a fast, fun downhill to a creek valley. It’s unclear how this road got its name, as Illinois isn’t a particular mecca for rattlesnakes, but be on the lookout just in case.


Be careful of the potential for large trucks on IL 100. Luckily, you will only be on the road for half a mile.

Almost all the climbing is in the last half. (Riding the route in reverse would make for an easier ride.)

If it’s a windy day, the open sections in the river bottoms can be challenging.

Do this ride if you are looking for a low-traffic, beginner-friendly ride in Scott County, Illinois with a pretty even split of pavement to gravel.

Other Notes:

The roads are generally in good shape and the gravel is packed and fast. During spring planting and harvest season, there can be some sections of deep fresh gravel to accommodate the farm vehicles.

Panaracer Gravel King SK 38 tires worked well but a slightly wider tire might be a better choice for the areas of deep gravel.

Park at the Rural Cyclery bike shop and stop in to say hi before starting your ride. This shop is run by a great couple who are very knowledgeable about the community. The shop offers a coffee bar and also has several varieties of adult beverages for after your ride.
There is plenty of parking on Main Street right near the bike shop

There are a number of local eateries where you could grab a meal afterwards.

Restrooms and refueling opportunities:
The route will pass through the town of Naples which lies right on the Illinois River (at approximately mile 25). There are no convenient stores but Evandy’s Boatel is a popular restaurant where you could stop in if necessary. This place often has live music on the weekends and is definitely worth stopping after your ride if time permits. Be aware that they are NOT open Monday-Wednesday.
A second option for rest stop and refueling is the Fast Stop convenience store in the town of Bluffs. At mile 34, you can turn left and ride about a mile to the town. There’s also a little ice cream shop in that area.

Driving Directions

Route Contributor

2022 Ambassador: Anne Schroll

Like so many others, I rode a bike as a kid but abandoned the hobby for years, picking it up again in my 40s. Rediscovering and developing a love for cycling started when my husband bought me a used Cannondale road bike, which served me well for a very long time. In 2016, I discovered gravel riding and the rest is history.  My passion is navigating and exploring the backroads of central Illinois with fellow cyclists. My husband, Steve, and I participate in numerous organized gravel events each year. I also enjoy mountain biking, doing it poorly but with great enthusiasm, and can still be seen occasionally on a road bike.

I retired in 2020 after 30 years as a graphics technician at an engineering company and keep busy volunteering as Marketing Coordinator for the Springfield Bicycle Club, a 300+member club based in Springfield, Illinois.

My favorite place to ride is Pike County in western Illinois. It is a beautiful and largely unpopulated area bordered by the Illinois River on the east and the Mississippi River to the west. The hilly, forested area is famous for world-class whitetail deer hunting, and many of the roads are navigable only by 4-wheel drive (or gravel bike!). A perfect day of gravel riding in this area would consist of parking at the courthouse square in Pittsfield and heading out into the countryside on the numerous gravel roads that crisscross the land.

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