Arrive in the postcard-worthy town of Red Lodge and explore the local shops, galleries and eateries on Main Street. Visit some of the furred and feathered residents of town with a tour at Yellowstone Wildlife Sanctuary. For dinner, there are enticing options galore: PREROGATIvE Kitchen (a James Beard nominee), Piccola Cucina at Ox Pasture, Black Canyon Bistro, Red Lodge Pizza Co., Carbon County Steakhouse, Bogart’s and more. Settle in for the night at the historic Pollard Hotel.

Grab breakfast at The Pollard — don’t miss their house-made doughnuts — then hit the slopes at Red Lodge Mountain. Ski bragworthy snow on 1,635 acres with an impressive 2,400 vertical, not to mention views from the top of the Grizzly chair that stretch all the way from the Beartooth Mountains to Wyoming. Take a break for lunch on the mountain, and before you call it a day, make sure to hop on the Palisades lift to see the famed Palisades rocks. Head back into Red Lodge for dinner and another cozy overnight. 

Awake early in Red Lodge and get a good breakfast at The Wild Table, Prindy’s Place or Café Regis — you’ve got a four-hour, hopefully snowy drive to the Anaconda/Philipsburg area ahead. You can always break up the trip with stops in Big Timber, Livingston, Bozeman, Three Forks or Butte. Once in Anaconda, don’t miss a visit to Anaconda Stack State Park to see the old Anaconda Copper Mining Company smelter stack, the town’s iconic landmark and one of the tallest free-standing brick structures in the world. Warm up at Smelter City Brewing and enjoy dinner at O’Bella! or Barclay II Supper Club. Overnight in Anaconda at Sugar Loaf Lodge & Cabins (for an off-the-grid experience), The Forge Hotel or the boutique Copperhead Lodge.

After a hearty breakfast in Anaconda at The Hangout Café, head up the mountain for a day at Discovery Ski Area. “Disco,” as it’s locally known, is the most expansive hometown mountain you’ll ever ski. With 2,200 acres, it has nearly as much swagger as a big ski resort, but local vibes prevail. Don’t miss the shortbread chocolate chip cookies at the base lodge.  After your runs, enjoy some local flavor at Philipsburg Brewing Company and then grab a “pizza with pizzazz” from Friday Night Pizza (Thursday-Sunday, takeout only) or head to Bunkhouse Whiskey for dinner. Overnight at the Broadway Hotel, the Kaiser House Hotel or the Inn at Philipsburg. If your family's in tow, be sure to visit the local gem shops and candy store.

Fuel up on breakfast in Philipsburg at your hotel or at the go-to Sunshine Station Tavern before your two-hour drive to Helena, Montana’s capital city. Explore downtown shops, galleries and eateries — popular spots include the walking mall and Reeder’s Alley. Then head to Broadwater Hot Springs, just 10 minutes from downtown, for a relaxing soak. Come dinnertime, enjoy brews and bites at Mt. Ascension Brewing Co. or a casual meal at The Hopper on the walking mall. Local-favorite eateries also include On Broadway and the Silver Star Steak Company. Stay overnight in Helena at Lamplighter Cabins & Suites, The Great Northern (the only Best Western Premier hotel in Montana) or at a local B&B, like The Carolina.

Eat breakfast in Helena before heading out to Great Divide, a locally owned ski hill. This powder playground boasts 1,500 acres across three peaks, with more than 100 runs. Grab lunch on the mountain at the Base Lodge Grill or pizza at Huggin’s Lodge and stick around — when the night skiing lights turn on the slopes are a blast. When you’re done skiing for the day (or the evening — there’s night skiing on Fridays and in January on Saturdays too), enjoy dinner and another overnight in Helena. (Note that Great Divide is closed on Mondays and Tuesdays but open on holidays that fall on Monday.)
 

Grab coffee and breakfast in Helena at Fire Tower Coffee, the Creperie or No Sweat Café (bring cash if you opt for this Helena institution). Take your time and enjoy three-hour drive through the stunning landscapes of the Rocky Mountain Front. Stop in Augusta for a bite to eat at Lazy B Bar and Café or Allen’s Manix Store, where you can pick up Made in Montana huckleberry items or a delicious maple bar made by “Papa Steve,” one of the owners. Then make your way to Choteau and explore this charming little community. Grab dinner at the Wagon Wheel Bar and Grill or the Livery Saloon and overnight at the Stage Stop Inn, perhaps relaxing with a dip in the indoor heated pool or a soak in the hot tub before turning in for the night. 

Stop into the Log Cabin Café, Outpost Deli, Copper Creek Coffee or John Henry’s for breakfast in Choteau and then head up the mountain to Teton Pass for a day on the slopes. This hidden gem has some of the most stunning views, diverse terrain and pristine snow of any ski hill around. Teton Pass covers 400 acres and has 43 downhill runs, with incredible access to backcountry skiing and boarding for those who like to shred the way back. Eat lunch on the mountain (the soup is excellent) and plan to enjoy dinner and a second overnight in Choteau. 
 

Get your fill of breakfast in Choteau before the scenic four-hour drive to Flathead Lake via U.S. highways 89 and 2. Once in the Flathead Lake area, explore the charming town of Lakeside. Sit down to dinner in Lakeside at Harbor Grille or Tamarack Brewing Company, then settle in with an overnight in Lakeside at Whispering Pines Cabins or drive the extra miles to spend the night in Kalispell at the historic Kalispell Grand Hotel. 

Enjoy breakfast in Lakeside or Kalispell before enjoying some family-friendly downhill skiing overlooking Flathead Lake. Blacktail boasts epic powder all winter long. It’s unique in these parts because the parking lot is at the top, with unparalleled views of Flathead Lake and Glacier National Park. Three chairlifts and a surface lift access 1,000 acres of powdery tree skiing, along with beginner and intermediate terrain. Grab dinner in the lakefront town of Bigfork at the Split Rock Restaurant or Flathead Lake Brewing Co., and if you’re staying another night, keep your after-dinner trip short by overnighting in Bigfork too, at the Mountain Lake Lodge or the Islander Inn.