Hancock, Maryland
Hancock bills itself as a "Trail Town Community," and I must say, it works hard to live up to that reputation. It has not one, but two major trails running through it, and local businesses work hard to cater to trail users.
C & O Bicycle is a one stop shop for bikers coming from the C & O trail and the Western Maryland Rail Trail. They provide food, gear, rentals, and even showers. If you are there in late summer or fall, they have the best apples under the sun.