Start in Bozeman [1], which has decent air service and is a good place to transition from the rest of the world to Montana. Use it as a place to decompress, but don’t make it your sole destination in this spectacular region.
While you’re settling in, visit the Museum of the Rockies [2] and spend an afternoon just wandering up and down Bozeman’s bustling Main Street. If you have a week to spend in this region, devote the first day to Bozeman.
Those with even a peripheral interest in the Lewis and Clark Expedition should plan to head to Three Forks [3] for day 2. Visit the Missouri Headwaters State Park [4], and make a side trip to the Madison Buffalo Jump, where Native Americans herded bison over the edge of a cliff. The Sacajawea Hotel [5] is downtown Three Forks’s biggest landmark and a fine place to spend the night.
On day 3, head south up the Madison River [6], around the corner at West Yellowstone (don’t bother to stop here unless you’re heading into the park), then down (north) the Gallatin River to the Big Sky [7] area. Either the 320 Ranch [8] or Buck’s T-4 make a good resting place. Stop and fish or hike.
Continue down the Gallatin back to Bozeman on day 4, head east, and spend the night in Livingston [9], maybe right downtown at the Murray Hotel [10].
Ramble around downtown Livingston’s galleries [11] in the morning of day 5, then head south to Chico Hot Springs [12] for the night.
Hike around Chico on day 6, then drive about 25 miles south to Gardiner [13] or Mammoth. Explore the extrahot hot springs in that part of Yellowstone.
On day seven, get up just before dawn and drive to Cooke City [14]. As the sun rises, keep your eyes open for wolves in Yellowstone’s Lamar Valley. Continue on the Beartooth Highway to Red Lodge [15]. If you’re continuing your journey to the east, spend the night in Red Lodge or Billings [16]. Otherwise, make it a long day by returning to Bozeman.
Links:
[1] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/bozeman
[2] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/bozeman/museums/museum-the-rockies
[3] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/three-forks-and-the-madison-river/three-forks
[4] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/three-forks-and-the-madison-river-/missouri-headw
[5] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/three-forks-and-the-madison-river-/accommodation-0
[6] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/three-forks-and-the-madison-river-valley/e/fishing-the-ma
[7] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/big-sky-and-the-gallatin-valley
[8] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/big-sky-and-the-gallatin-valley/accommodat/guest-ranches
[9] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/livingston-and-the-paradise-valley/livingston
[10] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/livingston-and-the-paradise-valley/livings/accommodations
[11] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/livingston-and-the-paradise-valley/arts
[12] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/livingston-and-the-paradise-valley/paradis/chico-hot-spri
[13] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/livingston-and-the-paradise-valley/gardiner
[14] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/absaroka-beartooth-wilderness/cooke-city-and-silver-gate
[15] http://www.moon.com/destinations/montana/the-missouri-headwaters-and-south-central-montana/absaroka-beartooth-wilderness/red-lodge
[16] http://www.moon.com/destinations/montana/billings/billings