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Autumn is celebrated in Oakland, and dordle upon your arrival, you will get the reason. This little hamlet hosts the Autumn Glory Festival each October, an annual five-day event that started in 1967. Oakland's scenic downtown is located just south of Swallow Falls State Park, which has cascading waterfalls and several hiking paths under a canopy of autumn foliage. Lenox is a picturesque East Coast town characterized by charming inns and undulating hills that really embrace the fall season. Situated in the Berkshires, it is the destination of choice during the yearly foliage transition. Explore the pond and path network at Pleasant Valley Wildlife Sanctuary, trek through the adjacent Kennedy Park, or have a picnic on the picturesque grounds of The Mount, the former home of Gilded Age author Edith Wharton, while seeing the dynamic transformation of autumnal hues.