Decisions, Decisions: Pick Your Holiday Weekend in Billings

October 27, 2026

Billings’ holiday calendar is filling up fast, with festive events, twinkling lights, live music, holiday shopping, and even a little Western flair. With so much happening across the city, the question isn’t whether you should visit Montana’s largest city this holiday season, but when?

That’s where we come in. We’ve rounded up four holiday weekends, each with its own lineup of events and local favorites to help you plan your trip and make the most of your stay. Think of it like a choose-your-own adventure, holiday edition. No wrong answers here, just plenty of ways to get into the holiday spirit. Now, the only decision left is which weekend to pick.

Weekend 1: For the Early Starters

Thursday, November 12 – Sunday, November 15 (3 nights)

This is for those who believe it’s never too early to get a head start on the holiday season (we see you)!The Main Events:

How We’d Do It:

Kick things off Thursday with dinner at Montana Brewing Company in Downtown Billings for all the festive vibes before catching A Celtic Christmas at Alberta Bair Theater.

Spend Friday exploring Billings at your own pace, whether that means checking out the exhibits at the Yellowstone Art Museum, grabbing lunch at The Granary, or taking in the views from the Rimrocks before cheering on the Cattle Punchers for an evening of hockey at Signal Peak Energy Arena.

Saturday is all about browsing the Holiday Food & Gift Festival, the biggest shopping market of the season with more than 200 vendors! Round out the weekend with a cozy dinner at City Vineyard, a stop at a brewery on The Billings Brew Trail, or a leisurely Sunday brunch at Sophie’s Kitchen before heading home.

Weekend 2: For the Nostalgia Seekers

Friday, November 27 – Sunday, November 29 (2 nights)

For many of us, Thanksgiving weekend means one thing: the holidays have officially arrived! Bring on the candy cane flavors, Christmas carols, and questionable decisions about how many gifts we can fit in the car. In Billings, that means holiday shopping, a downtown parade, and classic seasonal traditions.The Main Events:

How We’d Do It:

Start Black Friday with a little retail therapy on Billings’ West End at Shiloh Crossing or Rimrock Mall. When you’re ready to refuel, head to The Windmill for a bite to eat before heading downtown for the Annual Holiday Parade.

On Saturday, the shopping continues downtown, popping into local shops and stopping for a nice Italian dinner at Ciao Mambo. Save the evening for a holiday movie on the big screen at the historic Babcock Theatre, with Home Alone being a particularly fitting pick.

Wrap up the weekend Sunday afternoon with a timeless favorite, The Nutcracker Ballet, before heading home with your holiday spirit fully activated (and hopefully a few gifts checked off the list).

Weekend 3: For the Holiday Maximalists

Friday, December 4 – Sunday, December 6 (2 nights)

Feel up for a challenge? How about two days packed full of as much festive fun as possible (plus 15 million twinkling lights for good measure)?The Main Events:

How We’d Do It:

Start Friday by tracking down the best peppermint mocha in town (may we suggest a seasonal creation from Black Dog Coffee House or Big Sky Coffee Roasters?) before heading downtown that evening for the annual Holiday Stroll. Browse for gifts, explore local shops, and soak up the festive atmosphere as you walk the streets of Downtown Billings. P.S. – Make time for WinterFair at Yellowstone Art Museum, happening just a few blocks away!

Then comes the big decision: keep the holiday festivities going downtown or head to MetraPark for Styx. Yup, you read that right – Styx is in the house!

On Saturday, take part in the Festival of Trees, featuring rows of creatively decorated trees and live entertainment. Refuel with lunch or dinner by the fireplace at Copper Onion before bundling up for Holiday Nights at ZooMontana, where millions of lights transform the zoo into a festive nighttime experience.

And if you’ve made it this far, you’ve earned that hot cocoa and cinnamon roll at Stella’s Kitchen and Bakery on Sunday morning.

Weekend 4: For the Country Christmas Crowd

Thursday, December 17 – Sunday, December 20 (3 nights)

Trade the Christmas sweater for your favorite boots. This weekend brings together country music, holiday lights, western history, and the kind of rodeo action that makes for a very Billings way to celebrate the season.The Main Events:

How We’d Do It:

Kick off Thursday with country music as Chancey Williams takes the stage. Friday afternoon, tour the Moss Mansion, where the historic home gets dressed up for the holidays with festive décor and Christmas trees throughout. Keep the holiday magic going Friday night with a visit to Holiday Nights at ZooMontana with over 15 million lights on display.

On Saturday, lean into Billings’ historic side with a visit to the Western Heritage Center for Holiday Playapalooza. This free event invites children and families to explore Billings’ holiday traditions and history, along with the center’s current exhibits. Then, grab a hearty meal at Jake’s Downtown before heading to MetraPark for the main event: the Chase Hawks Rough Stock Rodeo, featuring top PRCA cowboys and some of the toughest bucking stock around.

Found your weekend? Now it’s time to make it happen. Start planning your trip at www.visitbillings.com.