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Image: Elle Michalka

Everything about the train ride from Portland to Whitefish, Montana—a tiny, postcard-perfect lakeside burg surrounded by the trailing peaks of the Rocky Mountains—feels like a vintage journey, in the grandest sense.

At Union Station, you board the Empire Builder, an overnight, Chicago-bound behemoth whose name recalls a national destiny not yet manifest. The gentle rocking of your compact sleeper car, the quiet formality of the dining room, and yes, the conductors wearing classic cylindrical hats—these are the flux capacitors powering this time-traveling machine. As the sun sets, the route glides you along the Washington side of the Gorge, until the Columbia River bends to the north. After Spokane, rugged forests and peaks take over. Open your compartment window’s curtains at night, and you’ll take in deep-blue, moonlit vistas of the Kootenai National Forest as the train carves a winding, lonely path through Idaho and Big Sky Country.

With just enough time to grab a coffee from the lounge car, you pull into Whitefish right along with the sun. Situated at the western edge of Glacier National Park, the tiny alpine town of 6,400 is an amalgam of cosmopolitanism (for Montana, that is) and a bygone brand of outdoorsy ruggedness. Come springtime, the winter thaw reveals a recreational paradise in blossom.

But the real key to unlocking this patch of Montana lies about 30 miles to the east, in the heart of Glacier National Park. There, more than a million acres of pristine wilderness beckon, including 700 miles of hiking trails, nearly 800 lakes, and countless species of birds and other animals. Adventurers who want to skip the quaint comforts of Whitefish can also take the Empire Builder straight to East Glacier, where the summer-only Glacier Park Lodge acts as a base station for exploration. If that doesn’t make you feel like a pioneer, nothing will.

Wonders of Whitefish

Hole up just west of town by the golf course at Grouse Mountain Lodge, a beautifully renovated chalet adorned in the local style: river-rock fireplaces and giant moose heads.

Start the day at Buffalo Café with a veggie and cheese–topped “buffalo pie” (hash browns form the crust), or deeply invigorating eggs and chiles rellenos.

Dive into one of the bubbliest, crunchiest, most thrilling bowls of mac and cheese you’ll find anywhere at Tupelo Grille, the “fanciest” restaurant in town. (Translation: don your best Patagonia for martini-sipping.)

Locals agree: Whitefish is having a real Moscow mule moment. For the best mule in town, the copper mug of vodka and ginger beer at Casey’s is unbeatable.

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