No matter the time of year, there’s always something to do in Big Sky. From going on a snowmobile tour through a winter wonderland to experiencing the beautiful fall colors, there’s adventure all around you. In addition to countless activities, Big Sky also hosts endless events throughout the year. When booking your vacation rental from Two Pines Properties, take a look to see if any of the memorable happenings line up with your getaway.
From sporting events to live music, the Big Sky calendar of events is filled with things that appeal to a wide range of interests. Keep reading to learn about seven popular options.
7 Things on the Calendar to Check Out
- One of the most anticipated winter events is the Best in the West Showdown. Taking place in February, the event combines horseback riding and skiing into one action-packed competition.
- From June through September, Music in the Mountains takes over Center Stage at Town Center. The weekly free concert series features the best up-and-coming musicians and more recognizable names.
- Stock your vacation rental with the freshest ingredients possible by shopping at the Big Sky Farmers Market. The open-air market takes place on Wednesdays from June through August and is filled with local farmers, artists, and community organizations.
- If you have any foodies in your group, you need to experience Savor Big Sky at least once. At the end of June, this celebration allows visitors to taste food, wine, and spirits from world-renowned companies.
- Mountain bikers take over town during Big Sky Biggie in August. With three distances to choose from, riders of all skill levels can take in breathtaking scenery. Proceeds from the event benefit the mountain bike trails committee.
- Big Sky Town Center goes all out for Halloween with the Haunted Peaks Halloween Festival. The three-day festival includes activities for all ages, including a costume block party, trick or treating, a haunted house, and more.
- There are plenty of things to do during the holiday season. The annual Christmas Stroll features sleigh rides, classic holiday movies, photos with Santa, and an illuminated walkway. There are also several events taking place at Big Sky Resort, like the Enchanted Forest.
Reserve Your Big Sky Rental from Two Pines

Some of the events above attract large crowds to Big Sky, so booking your vacation rental as soon as possible is important. Find your perfect home base by turning to the professionals at Two Pines. We can help you decide which of our Big Sky home or condo rentals fits within your budget. We can also explain how you can save on your stay with Two Pines Perks or other special offers. To learn more, call 406-995-2299.