The Top 4 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 4
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: October 26, 2025
Fort Hill Recreational Trail
Highlight (Segment) • Trail
The Fort Hill Recreational Trail is a 9-mile long multiuse trail that is built along the old Boston and Maine Railroad. The surface is crushed stone and gravel, so it is not suitable for road bikes.
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Mount Grace State Forest
Highlight • Forest
Fragrant trees, colorful wildflowers and quiet trails await you at Mount Grace State Forest. It's especially beautiful from spring through fall, when winter takes a break. Atop the 1,621-foot summit is a fire tower with prime views.
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Hubbard Hill Trail
Highlight (Segment) • Trail
The trail here is wide and easy, perfect for a peaceful forest walk. Be sure to check out Hubbard Hill Vista on the way to Baker Pond.
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Lily Pond Trail
Highlight (Segment) • Trail
The Lily Pond trail takes you on a beautiful pond walk that is especially stunning in the autumn. Keep an eye out for beaver dams!
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