Located roughly halfway between Bozeman and Yellowstone, Big Sky is a popular year-round destination for outdoor enthusiasts. However, I think winter in the region might be the best time to visit, especially if you are a skier or snowboarder. Big Sky is known to have some of the best powder conditions in the US. With 5,850 skiable acres and 4,350 vertical feet, on an average day, there is more than an acre of terrain for every skier. Furthermore, over the past decade, a lot of investment has been poured into both the resort and the main town with new shops, restaurants, and activities popping up every year. It is easy to spend anywhere from a long weekend to a couple of weeks in the region! Below is a 4-day winter itinerary that can be used as a long weekend getaway or in conjunction with a longer Yellowstone, Bozeman, or Jackson Hole itinerary - all three regions are within driving distance from Big Sky.
The best way to get around the region is by car. If you are flying into Bozeman, rent a car at the airport. In the winter, it is important that your car have 4WD or AWD (and perhaps even access to snow chains) as the road conditions can be unpredictable. If you hope to save costs on transportation, you may consider checking with your accommodation provider to see if they have shuttles from the airport and mountain village.
If you are skiing, I recommend staying in the Big Sky Mountain Village. It is pretty convenient to get around by foot. Shoshone Condominium Hotel, Huntley Lodge, Summit at Big Sky, and Big Sky Resort are very centrally located. There are also several rental homes available in the village that would make great options for larger groups or families. If you choose to stay in the Meadow Village (town), Lone Mountain Ranch and the Wilson Hotel are great options. I believe both of these places offer a shuttle service to the resort about 15 minutes away.
If staying in an Airbnb, rental home, or condominium, you will likely be doing some cooking. I recommend getting groceries in Bozeman, since it will have a much larger selection than Big Sky. We probably went to every grocery store in Big Sky to find what we were looking for (my friends had requested I make them a special meal). Below is my take on the three grocery stores in the region.
If you do not plan on cooking all meals, below you will find some good café, bar, and restaurant options in both the town and in the resort. You can find a list of more dining options on Big Sky Resort's website, including hours of operations and the ability to make advance reservations if necessary.
Big Sky's trail maps, including winter ski runs, can be found here. Our group consisted of pretty solid intermediate skiers that can comfortable ski all blues and some (to most) blacks. Our favorite runs included Freemont's Forest, Ambush Glades, Congo (through the trees), Big Horn (long cruiser) off of the Ramcharger chairlift and The Bowl and Steep & Deep off of the Powder Seeker chairlift. We spent a lot of time on Powder Seeker as the conditions were great that day. If you are up for you, you should also try the blacks (and double/triple blacks) off of Lone Peak Tram.
If you not a big skier or snowboarder, or are looking for other winter activities, Lone Mountain Ranch is a great place to check out and even stay. The ranch offers several winter activities like snowshoeing, Nordic skiing, and winter fly fishing, Yellowstone day tours, and dogsledding. Some of these activities require you to be staying at the ranch. You can book many of them through independent operators as well (i.e. dogsledding through Spirit of the North). Horn & Cantle is a restaurant located at Lone Mountain Ranch and is a great option for lunch, saloon (happy hour), or dinner. In the winter, they offer a sleigh ride dinner package that seems to be pretty popular.