The Art of the Stroll

November 2026

Article by Hannah Olson

Photos courtesy of Artwalk & DBA 

For more than three decades, the first Friday of every other month has given Billings a reason to wander downtown, step through a gallery door, meet an artist, or discover something unexpected. ArtWalk Downtown Billings began in 1994 to showcase the growing community of downtown artists and galleries. Now in its 32nd year, it includes 33 season members, with more artists, galleries, and businesses joining individual ArtWalks throughout the year, especially around the holidays. 

The final ArtWalk of 2026 may be the easiest one to experience it all. On Friday, December 4, ArtWalk joins the Downtown Billings Holiday Stroll, filling downtown with art, music, fire pits, holiday activities, locally made gifts, and plenty of reasons to linger. ArtWalk Director Jill Jussila-Patterson puts it simply: “We blend it together to just create this big event for everybody.” 

So bundle up, pull up the ArtWalk map, and start exploring. There is no required route, but here are a few ways to make the most of the night. 


1. Start Somewhere New 

ArtWalk reaches well beyond traditional galleries. For the evening, bookstores, shops, restaurants, creative spaces, and other businesses become places to discover artists and their work. 

Jussila-Patterson encourages artists to move between locations, too, knowing longtime visitors often develop their own ArtWalk routes. December is a good excuse to break from yours. Walk through a door you have never opened, and see what you find. 

2. Meet the Artist 

ArtWalk offers something scrolling through art online never can: the chance to meet the person who created it. At many locations, artists are on hand to answer questions, explain their process, and share the stories behind their work. 

Jussila-Patterson, an artist and MSU Billings BFA graduate herself, knows those conversations are not always easy for the artist. “Artists can be very vulnerable talking about their work,” she said. Building those connections between artists and audiences is a big part of what ArtWalk is about. 


3. Discover Someone New 

Jussila-Patterson makes a special effort to help emerging artists exhibit their work for the first time. 

 “I try to find those artists that have never shown before and push them to get out there,” she said. “Even if you’re a beginner and you don’t have a background and you’re self-taught, that’s okay.” 

For visitors, that means the artist whose work catches your eye this December could be someone showing publicly for the very first time. 

4. Shop for Something Made Here 

December gives ArtWalk a giftable twist, with many artists and locations featuring locally made pieces for the holidays. 

At Sandstone Gallery, a Billings artist co-op that has been downtown for more than 25 years, 11 member artists work in a range of mediums and styles. For December, its guest exhibition room will feature Billings Arts Association members and original seasonal pieces, including ornaments, gifts, Santa artwork, and winter scenes. 

Jussila-Patterson sees December as a chance to step away from online shopping and “find something a little more personal and connect with the community.” 

5. See Montana Through Another Lens 

At 207 N. Broadway, Billings native and professional wildlife photographer Seth Royal Kroft will welcome visitors to his downtown gallery. Kroft photographs wildlife and landscapes throughout Montana and the Greater Yellowstone Ecosystem, giving visitors a fresh look at familiar places and animals. 

6. Step Inside the Studio 

At 115 N. 28th St., Suite 304, impressionist oil painter Robert Tompkins will welcome visitors into his studio and gallery. His work bridges realism and abstraction, with original oils that include landscapes, florals, animals, and abstract pieces. 

It is a classic ArtWalk experience: stepping into a space you might otherwise pass by and finding an artist at work right in downtown Billings. 




7. Expect the Unexpected 

Kirks’ Grocery will host multiple artists in December, though its final lineup was still taking shape at press time. With season members and one-time participants joining each event, no two ArtWalks look exactly alike. 

That unpredictability is part of the fun. Follow the map, but leave room to wander. 

8. Make a Stop at WinterFair 

December 4 also brings WinterFair to the Yellowstone Art Museum, running from 11 a.m. to 8 p.m. Local artists and vendors fill the museum with handmade work, entertainment, refreshments and holiday shopping. Admission is free. 

Because it overlaps with ArtWalk and the Holiday Stroll, the YAM makes an easy stop before heading back toward Skypoint for the evening. 

9. Enjoy the Stroll Between Stops 

The Downtown Billings Holiday Stroll makes the walk between ArtWalk destinations part of the experience. Preliminary plans include free photos with Santa from 5 to 7 p.m., fire pits on Broadway, free transportation between downtown stops, and live music at the Northern Hotel and Yesteryears Antique Store from 5 to 8 p.m. 

Warm up, listen to some music, catch a ride to another part of downtown, and then look for the next ArtWalk sign. 

10. Follow Your Curiosity 

ArtWalk has changed since 1994, growing to include dozens of downtown locations and becoming an independent nonprofit in 2025. What has not changed is the simple idea at its center: bringing people and art together. 

So don’t treat the evening like a checklist. Talk to an artist. Wander into somewhere new. Buy something made by someone you just met. Listen to a musician, warm up around a fire, and keep walking. After 32 years, the best way to experience ArtWalk may still be the simplest: follow whatever catches your eye. 


ARTWALK AT A GLANCE 

Friday, December 4, 2026 | Downtown Billings 

ArtWalk generally runs from 5 to 9 p.m., and hours vary by location. Holiday Stroll activities are planned from 5 to 8 p.m., and WinterFair at the YAM runs from 11 a.m. to 8 p.m. ArtWalk is free and happens rain, snow, or shine. Check the current ArtWalk map before heading out for the latest participating artists, exhibitions, and locations. 

Originally printed in the November 2026 issue of Simply Local Magazine

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