It's hard to believe that Whitefish, Montana, was once called a swampy marsh. Its main drag, Central Avenue, is lined with boutiques and galleries, and tony inns dot the town. Before the railroad arrived in 1904, Whitefish was "full of green frogs, lizards, and other creeping things," according to an early account.
Whitefish's colorful history is detailed at the Whitefish Museum (in the Amtrak station; 406/862-0067). You'll learn how workers cut down so many trees to make way for the railroad that Whitefish was nicknamed Stumptown.
Walk north along Whitefish's three-block Central Avenue commercial district. Try on cowboy hats at the Toggery (122 Central Ave.; 406/862-2271). Bear Mountain Mercantile (237 Central; 406/862-8382) features bears carved, stuffed, glazed―and on boxer shorts. You can also rent a bike at Glacier Cyclery (326 Second St. E; 406/862-6446) and tool around the wide side streets dotted with flower-filled gardens.
Good stops for food are: Tupelo Grille (17 Central; 406/862-6136) for Cajun duck gumbo or Buffalo Cafe (514 Third St. E; 406/862-2833), famous for ham and eggs and local gossip.
Whitefish Mountain Resort (800/858-4157 or http://skiwhitefish.com/the-glory/), started in the 1940s by and for locals, is one of the Rockies' biggest resorts. Hike the 3.6-mile Danny On Memorial Trail up through huckleberries to the 6,817-foot summit or ride the gondola (and take your mountain bike for the trip down). Up top, allow time to visit the Summit Nature Center; you'll see a wildflower and wildlife exhibit and a display detailing the vistas (including Glacier National Park peaks).
If you want more time to explore the area, check in at Grouse Mountain Lodge (from $115; off U.S. 93; 877/862-1505), a 145-room cedar-log resort. For a cozier experience, there's the Garden Wall Inn (from $155; 504 Spokane Ave.; 888/530-1700); it's famous for its huckleberry-pear crêpes.
The perfect spot to wind up your visit is back in town at the Great Northern Brewing Company (closed Sun-Mon; 2 Central; 406/863-1000). You can sip a Buckin' Horse Pilsner, gaze out the window, and see the rail yards where the story of Whitefish began. And continues.