• Skip to main content
  • Skip to footer
  • facebook icon
  • instagram icon
  • LinkedIn
  • Guest Portal
  • Owner Portal
  • 406-995-2299
  • 406-995-2299

Two Pines Vacation Rentals

There's adventure between every Two Pines

  • Book now
    • All Big Sky Vacation Rentals
    • Properties by Location
    • Neighborhoods
    • 2 Bedroom
    • 3 Bedroom
    • 4 Bedroom
    • 5 Bedroom
    • 6 Bedroom
    • Ski In Ski Out Rentals
    • Tiny Homes
    • Single Family
    • Townhomes
    • Condo Rentals
  • SPECIALS
  • Join Our Catalog
  • logo
  • PLAN YOUR ADVENTURE
    • Attractions and Activities in Big Sky
    • Winter Activities
    • Summer Activities
    • Local Area Guide
    • Area Map
    • How to Get Here
    • Blog
  • ABOUT US
    • About
    • Meet the Team
    • Testimonials
    • Frequently Asked Questions
    • Terms and Conditions
    • Careers
  • facebook icon
  • instagram icon
  • Contact Us

Big Sky Winter Activities

Dec 13 2024

Winter Wonderland Awaits: Can’t-Miss Big Sky Winter Events

Snow encrusted peaks and squeals of delight from the ski runs. Twinkling fairy lights from frosted pine branches and cozy storefronts with smiling faces welcoming you home. Crisp mountain breezes and the smokey tang of a woodburning fireplace in the air. Sounds like a scene from a Hallmark film or a holiday card, right?

What if we told you that you could experience this and so much more in real life? 

These scenes are just whispers of the vibrant winter wonderland known as Big Sky, Montana.

During the snowy months from December to February (and often beyond), Big Sky is the “it” place to be to enjoy the picture-perfect winter. A tiny mountain town nestled just north of Yellowstone National Park, Big Sky is an exclusive hub for solo travelers and families seeking the ideal winter getaway. From snow-filled adventures and cozy nights in to quirky local traditions and classic winter activities, there are Big Sky winter events for all ages to enjoy. 

Looking for a winter adventure or maybe a relaxing snowscape to gaze at as you cozily sip hot cocoa? Big Sky can offer that and so much more! Keep reading to view our exclusive guide to winter activities in Big Sky. If you’re looking for the perfect base to call “home” while your exploring Big Sky’s many events, Two Pines Properties has the best local property rentals available. 

The Best Big Sky Winter Events 

Big Sky, Montana, comes alive in the winter months, offering a mix of festive celebrations, thrilling competitions, and unique cultural experiences that make it a must-visit destination. From late December through February, the beautiful town and surrounding areas host an array of events that showcase the spirit of this mountain community. Whether you’re looking to revel in holiday cheer, enjoy the thrill of winter sports, or take in world-class performances, there’s no shortage of ways to make your Big Sky winter getaway unforgettable.

We’ll explore the magic of Big Sky’s holiday events, the excitement of outdoor winter activities, and other fun-filled experiences waiting for you in this snowy paradise.

Big Sky Holiday Events

Riding your sleigh into Big Sky for the holidays? You’ve chosen the perfect place to experience the merriest time of year! Big Sky offers a wide range of holiday activities to help you make the season bright and ring in the new year. Let’s take a peek at the presents Big Sky has to offer for holiday activities:

1. Enchanted Forest Lighting Ceremony

Kick off the holiday season with the illumination of the Enchanted Forest on Andesite Mountain. This special lighting ceremony marks the opening of a winter wonderland, inviting guests to explore beautifully lit trails and festive decorations. 

When: December 11, 2024
Learn more: Bigskyresort.com/events/enchanted-forest-lighting-ceremony 

2. Christmas Stroll

Join the Big Sky community for the annual Christmas Stroll, a cherished tradition featuring tree lighting ceremonies, photos with Santa, illuminated cross-country ski and fat bike trails, sleigh rides, classic holiday films, carolers, and fireworks. The festivities span multiple locations—including the Big Sky Town Center, Nordic Center, and Meadow Village—so you can experience the best and brightest of Big Sky in a single night.  

When: : December 13-15, 2024
Learn more: Bigskyresort.com/events/christmas/christmas-stroll 

3. The Nutcracker Ballet

Experience the timeless magic of “The Nutcracker” performed by the Montana Ballet Company at the Warren Miller Performing Arts Center. Set to Tchaikovsky’s beloved score, this production is a holiday favorite for all ages. 

When: December 15, 2024
Learn more: Warrenmillerpac.org/event/nutcracker-montana-ballet/ 

4. Reindeer Visits

Meet Santa’s delightful reindeer at the Mountain Village Plaza. Learn about these majestic creatures before they journey back to the North Pole. 

When: December 20 and 23, 2024, 5:00pm to 7:00pm
Learn more: Bigskyresort.com/events/christmas/reindeer 

5. Pictures with Santa Claus

Capture cherished memories with Santa at the Mountain Village Plaza. Bring your wishlist and enjoy a festive photo opportunity. 

When: December 21 and 23, 2024, between 12:00 and 4:00 pm
Learn more: Bigskyresort.com/events/christmas/pictures-with-santa 

6. Holiday Cookie Decorating Class

Unleash your creativity at an all-ages cookie decorating class in the Cheyenne Room, Huntley Lodge. Registration is required for this festive activity. 

When: December 21 and 28, 2024, 4:00 pm to 5:30 pm

Learn more: Bigskyresort.com/events/christmas/cookie-decorating-dec-21 

7. Holiday Cocktail Creation

Join expert mixologists for a holiday cocktail creation class, where you’ll learn to craft festive beverages. This class is for guests 21 and over.

When: December 22, 27, and 30, 2024, 8:00 pm to 9:00 pm
Learn more: Bigskyresort.com/events/christmas/holiday-cocktail-class-dec-27 

8. Holiday Trivia

Test your festive knowledge at Westward Social. Enjoy a spirited game of trivia alongside delicious dinner and drinks. 

When: December 23, 26, 29, and January 1, 2025
Learn more: Bigskyresort.com/events/christmas/holiday-trivia 

9. Fireworks & Torchlight Parade

Marvel at a stream of lights descending Andesite Mountain during the torchlight parade, followed by a spectacular fireworks display visible from Mountain Village. 

When: on December 24, 2024, 8:30 pm
Learn more: Bigskyresort.com/events/christmas/fireworks-and-torchlight-parade 

10. Skiing with Santa

Hit the slopes with Santa Claus, Mrs. Claus, and the elves! Catch them on the mountain and in the base areas, adding a festive touch to your skiing experience. 

When: December 24 and 25, 2024
Learn more: Bigskyresort.com/events/christmas/skiing-with-santa 

11. New Year’s Eve Fireworks

Ring in the New Year with a dazzling fireworks display at Big Sky Resort. The festivities include gourmet dining, live music, and family-friendly activities, culminating in a vibrant celebration. 

When: December 31, 2024, 9:00 pm
Learn more: Bigskyresort.com/events/new-years-eve/fireworks 

12. New Year’s Eve Party

Dance the night away at Montana Jack’s New Year’s Eve Party. Enjoy music, dancing, and celebration as we bid farewell to 2024 and welcome 2025. This event is for guests aged 21 and over; tickets are required.

When: December 31, 2024, 9:30 pm
Learn more: Bigskyresort.com/events/new-years-eve/new-years-eve-party 

13. New Year’s Eve Masquerade Ball

Celebrate in style at The Waypoint’s Masquerade Ball with live music, drink specials, and a champagne toast. Dress to impress for the Best Dressed Contest!

When: December 31, 2024
Learn more: Visitbigsky.com/event/nye-masquerade-ball/1522/ 

Big Sky Winter Outdoor Activities 

In the winter, Big Sky transforms into a playground of wonder, offering an array of activities that immerse you in its stunning snowy landscape. Whether you’re carving down world-class ski slopes, exploring peaceful snow-covered trails, or experiencing the thrill of dogsledding or snowmobiling, every moment in Big Sky is a chance to create unforgettable memories.

1. Snow Sports 

  • Skiing & Snowboarding: Experience the “Biggest Skiing in America” at Big Sky Resort, boasting over 5,850 acres of skiable terrain suitable for all skill levels. Whether you’re a novice or an expert, the resort offers diverse runs to match your abilities. 

    Learn more: Bigskyresort.com 
  • Skiing & Snowboarding Lessons: Enhance your skills with professional instruction available for both skiing and snowboarding, ensuring a safe and enjoyable experience for all ages. 

    Learn more: Bigskyresort.com/lessons 
  • Nordic Skiing & Snowshoeing: Lone Mountain Ranch boasts 80 kilometers of world-renowned groomed cross-country ski trails, offering an unforgettable Nordic skiing experience. Voted the #1 Nordic Ski Resort in North America by Cross Country Skier magazine, the ranch caters to every type of skier and snowshoer.

    Learn more: Lonemountainranch.com/perfect-ski-trip-big-sky/ 

2. Outdoor Adventures

  • Snowmobiling: Embark on thrilling snowmobile tours through the Gallatin Canyon or venture into Yellowstone National Park to witness iconic landmarks like Old Faithful. These guided adventures cater to both beginners and seasoned riders, offering an exhilarating way to explore the winter landscape. 

    When: Available throughout the winter months. Check listings for availability.
    Learn more: Backcountry-adventures.com/ 
  • Dogsledding: Your guides will provide hands-on instruction and expert tips, allowing you to experience the exhilarating thrill of driving your own sled dog team. Picture yourself gliding through a snowy wonderland, surrounded by Montana’s majestic mountains, as a team of spirited Alaskan huskies leads the way. Their high spirits and lovable personalities are sure to capture your heart in no time.

    When: Available throughout the winter months. Check listing for availability.
    Learn more: Huskypower.com 
  • Snowcoach Tours: Discover the winter wonders of Yellowstone National Park aboard a heated snowcoach, offering comfortable access to geothermal features and wildlife sightings amidst the snowy backdrop. These tours are ideal for families and groups seeking a relaxed yet immersive experience.

    When: Available throughout the winter months. Check listing for availability. 
    Learn more: Backcountry-adventures.com

Local-Favorite Winter Events

1. Warren Miller’s Performance Arts Center

MPAC hosts a diverse lineup of world-class performances throughout the winter season, including music, theater, and dance, enriching Big Sky’s cultural scene. One of the amazing events they host is International Guitar Night. Scheduled for February 20, 2025, this event features a captivating evening with renowned acoustic guitarists from around the globe, offering a unique musical experience.

Learn more: Warrenmillerpac.org/ 

2. Best In The West Showdown

Witness the excitement of skijoring—a unique sport where a skier is pulled by a horse through a course of jumps and obstacles. This family-friendly event also features live entertainment and festivities, capturing the adventurous spirit of Big Sky.

When: February 8-9, 2025
Learn more: Bigskytowncenter.com/annual-events/ 

3. Winter Farmers Market

Explore local crafts, produce, and artisanal goods at the Big Sky Winter Farmers Market. It’s a delightful way to engage with the community and find unique souvenirs. 

When: Available throughout the winter months. Check listing for availability.
Learn more: Bigskytowncenter.com/farmers-market/ 

4. Country Dance Nights

Put on your dancing boots and join the locals for an evening of country dancing. These events are filled with lively music and are a fantastic way to experience Big Sky’s vibrant community spirit.

When: Recurring weekly on Wednesday
Learn more: Visitbigsky.com/event/country-dance-nights/1185/ 

5. Montana Dinner Yurt

Discover the enchantment of dining under Montana’s Big Sky at the Montana Dinner Yurt. Begin your adventure with an exciting ride through the picturesque backcountry in a rugged army truck, leading to a cozy yurt nestled amidst breathtaking views. Inside, indulge in a hearty, three-course meal crafted with care and bursting with flavor. Whether you’re marking a special occasion or simply looking for a one-of-a-kind dining experience, a night at the Montana Dinner Yurt promises unforgettable moments and cherished memories.

When: Availability throughout the winter months. Check listing for reservations.
Learn more: Bigskyyurt.com 

6. Sleigh Ride Dinner

Take a magical 20-minute sleigh ride through snowy trails under a sparkling night sky to the historic North Fork Cabin. Inside, savor a three-course, family-style meal of mouthwatering dishes, such as \ prime rib slow-cooked on a century-old stove, mashed potatoes, and huckleberry cobbler. Cowboy singer-storytellers add charm with songs and tales, creating an unforgettable evening.

When: December through April
Learn more: Lonemountainranch.com/sleigh-ride-dinner/ 

Why Stay with Two Pines Properties

When it comes to experiencing the best of Big Sky in winter, Two Pines Properties is your trusted partner. Our vacation rentals are strategically located to provide easy access to the area’s most exciting winter activities and events, from the thrill of skijoring to serene snowshoeing trails. Whether you’re here for family fun, a romantic getaway, or an adventurous retreat, our homes put you right in the heart of the action.

What sets Two Pines apart is our personalized service and local expertise. We’re more than hosts. We’re your local guides, ready to help craft a seamless and unforgettable winter itinerary. Our team’s insider knowledge ensures you’ll discover hidden gems and make the most of your time in Big Sky.

After a day filled with snowy adventures, return to the comfort and warmth of a Two Pines property. From cozy fireplaces and luxurious hot tubs to fully equipped kitchens for family meals, our amenities are designed for relaxation and connection. Here, you’ll find all the comforts of home—and then some.

Plan Your Winter Escape with Two Pines

Big Sky is calling, and winter is the perfect time to answer. With its dazzling array of events, world-class outdoor activities, and breathtaking mountain scenery, this destination offers something for everyone. Two Pines Properties is your key to experiencing it all with ease and style.

Ready to experience the best of Big Sky this winter? Explore our vacation rentals today and start planning your unforgettable getaway!

Written by Drew Schug · Categorized: Big Sky Events, Things to Do in Big Sky, Montana Winter · Tagged: Big Sky Winter Activities

Oct 09 2023

Embrace Winter on a Montana Getaway in Big Sky

Big Sky is the perfect destination for anyone looking to spend as much time outdoors as possible. No matter the time of year, there is always something to do that will surround you with Mother Nature’s beauty. This is especially true during the winter. Get the most out of your Montana winter escape by reserving a vacation rental from Two Pines Properties. 

Our cozy Big Sky rentals put you close to some of the best things to do. They’re also the perfect place to rest up after a long day out in the snow. To help you have the best time possible, our team has put together a list of memorable activities. Because our team is made up of those who call Big Sky home, we have tried many of these things to do ourselves. We feel confident you’ll love them as much as we did! If you plan on bringing your own equipment, check out Ship Skis, which offers our guests door-to-door shipment.

7 Top Big Sky Winter Activities

  1. Big Sky is a top destination for skiers. Read our post about how to plan for a ski vacation, which includes all the tips you need to make the most of your time at Big Sky Resort.
  2. Explore the snow-covered landscape on an outing with Spirit of the North Dog Sled Adventures. Your outing will take you through Moonlight Basin.
  3. Make your reservation for a Sleigh Ride Dinner at Lone Mountain Ranch. The horse-drawn sleigh will bring you to a cabin where you’ll enjoy a family-style prime rib dinner.
  4. Another popular activity at Lone Mountain Ranch is cross-country skiing, also referred to as Nordic skiing. With more than 50 miles worth of trails, there are paths for skiers of all skill levels.
  5. See what Yellowstone National Park looks like when blanketed with snow on an outing with Back Country Adventure. In addition to snowmobile tours, they also offer snowcoach tours.
  6. In addition to beautiful nature, the national park is also home to countless animals. Reserve your spot on a winter wildlife safari with Backcountry Safaris to see how many of these majestic creatures you can see.
  7. For another unique dining experience, check out the Montana Dinner Yurt. Enjoy a three-course meal inside a cozy yurt, complete with a crackling wood fire stove and live music.

Stay Cozy at Your Two Pines Rental

The bedroom of a Big Sky vacation rental to stay in on a Montana winter vacation.

After a long day out in the snow, there’s nothing better than curling up with a big cup of hot cocoa and your favorite movie. By staying at a Two Pines rental for your Montana winter vacation, you can do just that and more. Each of our Big Sky rentals has all the comforts of home, making the perfect home base for everyone from families to couples.

If you’re staying with us over the winter, we highly recommend checking out our ski-in, ski-out rentals. To learn more about these properties or other Big Sky accommodations, call 406-995-2299. When you’re ready to book your stay, check out our special offers for ways to save.

Written by SEO Atlas · Categorized: Big Sky Rentals, Big Sky Montana Vacation Rentals, Skiing in Big Sky Montana, Things to Do in Big Sky, Montana Winter · Tagged: Big Sky Rentals, Montana Vacation Rentals, Montana Winter, Lodging in Big Sky Montana, Big Sky Lodging Ski In Ski Out, Big Sky Winter Activities

Footer

  • Guest Reviews
  • Contact Us
  • Join Our Catalog
  • Owner Login
icon facebookicon instagram icon linkedIn

Explore Our Properties

Two Pines Properties, LLC.

99 Lone Peak Drive

Big Sky, Montana 59716

Local: 406-995-2299

[email protected]

© 2025 Two Pines Properties, LLC. All rights reserved.

  • Terms of Use
  • Privacy Policy
  • Sitemap
  • Owner Login

Powered by