Have you ever thought to yourself, “Man, I’d really like to spend a weekend with friends. We should go to Billings.” Yeah, me neither. But when I had an opportunity to spend a long weekend here with a group of travel bloggers, I was so wonderfully surprised by this little city.

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Billings has always conjured up images of the wild west. Perhaps a train depot with tumbleweed in the streets, or cowboys in old pickup trucks returning from whatever ghost town they had come from. While Billings did put John Denver songs in my head on repeat, the western vibe meshed perfectly with the hipster tones that make Montana’s Trailhead so inviting.

This begs the question then: What does one do in Billings?

While there’s plenty to do in Billings, most of my time was occupied with the conference, yet I still got a great flavor for ways to spend time in Billings:

The people

I’m starting with the end here, but the moment that sums up Billings for me the most is an encounter in a coffee shop as I was leaving town.

I walked into Yellowstone Coffee & Canvas and immediately noticed the hodgepodge of paintings on the walls and easels set up on tables waiting to be filled with blank canvases. The space could accommodate crowds, but save for the art supplies and finished products, the place was empty. I suppose that’s normal for 10 am on a Saturday.

This is where it gets fun. I was greeted by a woman who I learned was named Billie. Billie was the kind of person that pulls stories out of people effortlessly. Before I knew it, I had a drink recommendation and we were chatting about our dreams to write books in the future. She told me about the mission of the coffee shop and how people can go in and paint any time – creative expression is integral to the community they’ve created around their coffee.

The thing is, while Billie is incredible, she isn’t unique in Billings. What I mean by that is that the folks in every coffee shop, hotel front desk, and everything in between, were so incredibly kind. I come from the Midwest originally, and Billings outdoes the Midwest in nice. Hands down.

The city is known as Montana’s Trailhead because people coming from the East stop there on their way to the skiing in Big Sky, the adventures in Yellowstone National Park, and the thrills in Glacier National Park – all of these destinations are about 3 hours away. Shouldn’t every trail start with a smile?

The brew trail

Every good vacation in my book includes a great local beer scene, and Billings nails it. Not only are most of the breweries close together and in an area of town that lends to other tourism, but the local tourism board has a convenient map that navigates the best way to visit all the breweries, distilleries, and alehouses in the downtown area.

Visit Billings arranged a 4-stop tour for several of the conference attendees that included tours and samples at each stop. The brewmasters were all so fun to listen to and the guide that took us from stop to stop was full of jokes and additional Billings information.

A note on accessibility: the sidewalks in Billings are constructed in such a way that people in wheelchairs are able to get to each brewery. Of the four I visited plus one on my own time, Yellowstone, Montana Brewing Company, Uberbrew, and Thirsty Street are all at street level. There is a ramp inside of Last Chance brewing.