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Best Affordable Fall Foliage Towns

Middlesboro, KY (Near Cumberland Gap)

Courtesy The Cumberland Manor Bed and Breakfast

Middlesboro, KY

With a charming historic downtown, Middlesboro is close to the Cumberland Gap, which was the gateway to the West for countless pioneers, including Daniel Boone. Two hours south of Lexington, KY, it’s far less crowded than the better-known Great Smoky Mountain National Park. If you want to see peak colors on the sugar maples, beech, birch, and basswood, plan to travel here from mid- to late October.

Fall Color Hotel: The Cumberland Manor Bed and Breakfast is a grand Victorian home dating from 1890 with five guest rooms. Doubles from $99.

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