A Festive Weekend in Billings: Your 48-hour Itinerary this Holiday Season

November 11, 2025

Traveling to Billings this holiday season? We sure hope you are—it’s an amazing time of year to visit. Festive traditions, wintertime activities, and Santa-approved sweets are plentiful, and you only need a few days to warm up your holiday spirit!  Check out this itinerary to find inspiration for your next stay. Whether you want to brave the frosty weather or warm up next to the fireplace, we’ve got you covered. 

Morning (1st Day) – Bundle Up for a Bite

There’s something about fresh bakery bites, especially this time of year. Kick off your first morning with a visit to a local favorite and fuel up for the day ahead. Stella’s, Black Dog Coffee House x 10th Ave, Flours Bakery, and the Caramel Cookie Waffle are all tasty bets! 

Local Tip: If you’re visiting on a weekday, add Veronika’s Pastry Shop to the recommendations above. Just plan to get there early—she’s known to sell out by midmorning! 

Stellas

Midday (1st Day) – Explore Downtown Billings

Downtown Billings is always fun to explore, but it feels more magical when the temperature drops and holiday decorations are on display. 

Enjoy the scenery, warm up at a local coffee house, and shop locally for your friends and family (or yourself, we won’t tell anyone…). 

Local Tip: The downtown Billings Holiday Stroll starts at 5pm on December 5th. This annual event is a fun evening for couples and families. Don’t forget to get your picture taken with Santa! 

Christmas Santa Stroll

Evening (1st Day) – Enjoy a Show at the Theater

This year, the creative team at Billings Studio Theater will delight audiences with Rudolph the Red-nosed Reindeer, and the NOVA Center for the Performing Arts is offering a festive mash-up with their seasonal play, A Seussified Christmas Carol. 

If you’d prefer a night with the silver screen, the Art House Cinema & Pub is open seven days a week, and you can always count on a great movie with concessions that won’t break the bank. 

Arthouse Cinema

Morning (2nd Day) – A Short Drive for the Great Outdoors

Start your second day in Billings by enjoying some time outdoors! A refreshing walk with stellar views is always an option at Swords Park or Zimmerman Park.

If you’re feeling more adventurous, and there’s fresh snow, Riverfront Park is a great location for snowshoeing or cross country skiing, or you can race downhill on a sled at Pioneer Park. 

Midday (2nd Day) – Find Stocking Stuffers & Sip on Something Warm

After your morning outing, shop at a few stores to find gifts and stocking stuffers, and continue to enjoy Billings’ food scene! 

A visit to Gainan’s Flowers, Made for Home, and Scheels will help you tackle wishlists. 

Shopping Downtown

Don’t forget to treat yourself either! Find something sweet to nibble on at Brockel’s Chocolates or Candy Town, and you can sip on something delicious next to the fireplace at Last Chance Pub & Cider Mill

Local Tip: Some of Billings’ best holiday shopping can be found at pop-up shops and holiday markets. If you’re visiting in early December, check out the Yellowstone Art Museum’s WinterFair

Last Chance Pub & Cider Mill Flight

Evening (2nd Day) – See the Sights? See the Lights! 

Wrap up your time in Billings by taking in the sights and holiday lights! 

There are multiple neighborhoods known for their extravagant displays, and you can always plan to visit Holiday Nights at ZooMontana this time of year.

ZooMontana Lights Dome 

Whether you’re traveling to Billings for the holidays or enjoying a staycation to find some quiet during the busy season, we hope you enjoy your time here. Happy holidays!