The Top 20 Attractions around Winchester
There are plenty of places to see and visit around Winchester. Whether you love hiking or cycling, Winchester is a region where 20
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: December 9, 2025
Meramec Greenway Trail – Eastern Section
Highlight (Segment) • Trail
Neat trail close to the Meramec. Good surface, but lots of turns (can’t go too fast).
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Lone Wolf Trail
Highlight (Segment) • Viewpoint
The Lone Wolf Trail is right in the heart of Castlewood State Park. The trail shares a path with the Riverscene Trail very briefly near an observation deck and also …
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Meramec Greenway Trail
Highlight (Segment) • Trail
The Meramec Greenway Trail is a scenic route that connects riders to the Meramec River and many parks in the region as it winds along the river and limestone bluffs through woodlands and several communities.
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Forest 44 Conservation Area
Highlight • Forest
The Forest 44 Conservation Area directly borders Lone Elk County Park and is just across the street from Castlewood State Park. There are a handful of grassy trails on the …
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Al Foster Trail
Highlight (Segment) • Trail
The Al Foster Trail is a long point-to-point trail passing through parts of Sherman Beach Park and Castlewood State Park. The path is mostly packed gravel and smooth dirt, but …
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Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:
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