As far as Kentucky, there's the Red River Gorge and Mammoth Cave National Park; relatively small elevation gains and losses, but pretty. The Smokies, Virginia's Grayson Highlands, and West Virginia's Dolly Sods are a bit further, and have some more challenging terrain, but are very pretty.

Don't overlook southern Ohio - Zaleski in particular; also some other spots in the same area.

And about the same distance north, don't overlook Isle Royale NP and Pictured Rocks.

None of these places are Montana, but you can get to them easier and more often, and you'll find that they have their own particular brand of charm.