5-Day Big Sky Winter Itinerary

Big Sky Vacation Rentals offer a hand-picked selection of over 125 luxury vacation rentals in prime locations throughout Big Sky. We’ll find you the perfect home to suit your Big Sky vacation itinerary and assist with vacation planning to ensure your 5-day getaway to Big Sky is a special experience.

To help you plan your stay, our local team has put together the best of Big Sky from dining, après-ski to the best activities! Here are our suggestions for unique ways to experience the best of Big Sky in 5 days.

Day 1: Stay Local In Big Sky

Slope Side Breakfast: Day 1 deserves a slope side breakfast at Big Sky Resort to get your bearings and switch slowly to mountain time. Vista Hall is Big Sky’s newly renovated food court with views of the ski runs, inviting fireplaces and a delicious European style café & bakery with fresh roasted coffee and breakfast pastries to start your day.

Ski Big Sky Resort: Big Sky Ski Resort boasts 5,850 acres of terrain with over 400 inches of the greatest snow on earth, groomed runs for every skiers and snowboarder in your group and extreme off-piste skiing for the adventurous. With 39 lifts and over 300 named runs ranging from wide-open groomers to challenging steeps, we suggest you plan your day on the slopes in advance!

Lunch: If the conditions are good and the adrenaline is rushing, make a quick pit stop at Yeti Dogs in Mountain Village for quick service and the best hot dogs in Big Sky or ski-in to warm up at The Exchange. The Vista Hall food-court has plenty of options for you to enjoy.

A Local Big Sky Dinner: Big Sky Town Center and Meadow Village have many enticing eateries ranging from wood-fired pizza at Ousel & Spur to traditional Asian and Thai cuisine at Blue Buddha or Lotus Pad and elegant fine dining. Whether you’re visiting Big Sky with kids, friends or your beloved beau, you’ll find the perfect dining experience locally in Big Sky.

Late Night Drinks: Save space for dessert and after dinner drinks at The Standard, Big Sky’s best cocktail lounge in the heart of Big Sky’s Mountain Village. The Standard is Big Sky’s hottest new après ski spot with a selection of local beer and wine, over 50 hand-crafted cocktails, warm, spiked after dinner drinks, and a delicious dessert bar.

Day 2: Big Sky Backcountry

Breakfast in Meadow Village: Start your day with a hearty and nourishing organic breakfast at Acre Kitchen, a trendy eatery in Meadow Village. Acre offers a fun and flavorful farm-to-fork experience with all you need to fuel your day of adventures in Big Sky’s beautiful backcountry.

Snowmobiling: Snowmobiling in Big Sky is a must-do experience and is geared for the whole family. Play in the powder fields and open meadows of Gallatin Canyon on a Big Sky snowmobiling adventure or take it full throttle and book a guided snowmobile tour of Yellowstone National Park surrounded by majestic mountain peaks, frozen waterfalls and winter wildlife.

Fireside Après Ski: Let the spirit of adventure continue at Copper Whiskey Bar in Big Sky’s Wilson Hotel. Lounge by the fire with an old-fashioned or sip spicy margaritas, share ski stores with friends round the outdoor firepit and warm up for a night of more Big Sky adventures at one of the best après ski spots in Big Sky.

Dinner in a Yurt: It’s not often you get to ride a snow cat to dinner, sled by torch light with the kids, sing along to acoustic tunes and enjoy a candlelit dinner in a secret Yurt on the slopes of Lone Peak! The Montana Dinner Yurt offers the most unique dining experience in the backcountry of Big Sky. Be sure to book ahead!

Day 3: Unique Big Sky Experiences

Breakfast: You’ve only scraped the surface of Big Sky’s endless terrain so it’s time to get back on the slopes. Plan your ski day with breakfast at home or gather the crew and start your day slopeside with pancakes or a hearty omelet at the Carabiner Lounge in Mountain Village.

Ski Big Sky Resort: Sharpen your skills at Big Sky’s seven terrain parks or ride the Lone Peak Tram to discover the terrain at the summit of Lone Mountain. While the easiest run off Lone Peak is a steep black diamond, the journey is worth it for the 360-degree views of 3 states, 2 national parks and the spectacular peaks surrounding Big Sky Resort.

Slope Side Lunch: It’s time to take a break to refuel. Mountain Village has lots of ski-in eateries for a quick lunch break (dine in or to-go!) or make your way to the Madison Village Base Area on the Moonlight side of Big Sky for lunch on the slopes at Headwaters Grille.

Sick of Skiing? Explore the beautiful scenery on over 85 kilometers and 2,200 vertical feet of groomed cross country ski trails right out of Big Sky. Lone Mountain Ranch was voted #1 Nordic ski destination in North America in Cross Country Skier magazine and certified instructors available, they invite skiers of all abilities to venture out on the trails.

Big Sky Brewery Experience: Quench your thirst with a cold craft brew at Beehive Basin Brewery, Big Sky’s newest brewery. Beehive Basin is a seven barrel microbrewery and taproom with a rotating selection of seasonal brews, Big Sky mountain views and a fun ski-town vibe.

Dinner on the Ranch: From a star studded dinner in a yurt to fine dining in a historic Montana ranch lodge! Lone Mountain Ranch offers an authentic Montana culinary experience at the authentic saloon bar and the intimate Horn & Cantle Restaurant. Savor the best of the west, paired with signature cocktails, local Montana beers and an impressive wine list.

Day 4: Discover yellowstone's natural wonders

Sunrise Breakfast: With a full day of adventures ahead, it’s an early start! Pick up a quick coffee and breakfast pastry at Caliber Coffee Roasters or a grab-n-go breakfast on your way out of town at Café 191 in Big Sky Canyon Village.

Yellowstone Park Winter Tour: Yellowstone is a natural wonderland that is even more beautiful under a blanket of snow. Only a one-hour drive from Big Sky, Yellowstone is easily accessible and an experience not to be missed. You’re welcomed by vast snow-covered plateaus with free roaming elk, wolves and moose, frozen waterfalls, thermal pools, erupting geysers and spectacular natural wonders.

Take a self-guided tour or book a winter tour of Yellowstone from Big Sky. Yellowstone Guidelines offer snowshoe, cross-country ski and wildlife tours throughout the winter or book a guided Yellowstone tour from Big Sky Meadow Village with Yellowstone Scenic Tours.

Not looking to drive that far or looking for something for young children? Consider a dog sled adventure through beautiful Moonlight Basin or a traditional horse-drawn sleigh ride and family-style dinner at Lone Mountain Ranch.

Dinner on the Gallatin River: The Riverhouse is a Big Sky attraction and locals favorite! Located just outside of Big Sky (and conveniently on the way home from Yellowstone) on the banks of the Gallatin River, the Riverhouse serves up authentic Texas BBQ with a Montana twist. As they say, “it’s a smokin’ good time” at Riverhouse BBQ.

Day 5: create lasting big sky memories

Breakfast in Bed: You’re exhausted, we get it! There’s so much to do in Big Sky but today it’s breakfast in bed, a soothing hot tub and slow start at home. BSVR kitchens are well-equipped (and pre-stocked if you choose) to whip up a home-cooked meal any time of the day! If you’ve got ski-in/ski-out access to Big Sky there’s no rush at all!

Breathe in the Crisp Mountain Air: It’s your final day in Big Sky so be sure to get outdoors and breathe in the crisp mountain air! This may mean heading back to your favorite ski runs or terrain park, fly-fishing on the Gallatin River, heading off the trails on a backcountry snowshoe hike or early après ski on a sunny outdoor patio. Savor the day and make lifelong memories in Big Sky.

Lunch at the Summit: Wherever you roam, we suggest reserving a table for lunch at Everett’s 8,800 for a Big Sky mountain-top dining experience at the summit of Andesite Mountain. This beautiful timber lodge boasts unbeatable Lone Peak views from the indoor dining area and outdoor deck with roaring fireplaces, exceptional alpine cuisine and an elevated dining experience.

Après Ski: Soak up the Big Sky après-ski scene with one last drink on the mountain. Grab a snack from the Vista Hall food court, enjoy a cocktail or cold brew and get a final picture perfect shot of Lone Peak at the Vista Bar in the Mountain Village Exchange.

Dinner on the Mountain: Enjoy cozy and casual fine dining at the Cabin Bar and Grill, overlooking the ski runs in the heart of Big Sky’s Mountain Village. Delectable Rocky Mountain cuisine, a full bar and extensive wine list, Big Sky views and take-out if you’d prefer to dine in the comfort of your luxury Big Sky vacation rental.

5-Day Big Sky Winter Itinerary

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