Winston’s Guide to the Perfect Girls’ Weekend in Billings

September 9, 2025

I was checking the analytics on my Instagram, and almost 90% of my followers are human females. So yes—apparently I’m a bit of a ladies’ man. (It’s the slow confidence.)

Naturally, that qualifies me to help plan the perfect girls’ getaway in Billings… but just to be safe, I consulted my expert panel: Uki the badger and Roxy the box turtle. They insisted the weekend needs a proper order of operations: coffee first, brunch second, then shopping, a little arts-and-culture moment, the Brew Trail, and finally… a visit with your favorite sloth (me).

Coffee stops for very important conversations

Every girls’ weekend needs a cozy coffee break—preferably somewhere you can sit for a while and recap everything (I support this deeply).

  • Black Dog Coffee House – Great vibes, great coffee, and an excellent place to warm up between stops.
  • Marble Coffee Co. – Another must for caffeine and catch-ups—perfect for plotting your next move, whether that’s shopping… or more coffee.

Brunch is non-negotiable

You’re going to want brunch—and Billings absolutely delivers.

Shop ‘til you drop (or gently sit down)

Let’s do shopping next, because it’s my least favorite form of cardio.

Downtown boutiques:

Pop into Cricket Clothing and SOMETHINGchic for fun, curated finds and that “new outfit energy” you can wear straight to brunch.

More downtown favorites:
For modern Montana style and thoughtfully selected goods, check out Frae Collective and slow your pace (my specialty) at This House of Books. Then swing by Zest Kitchen & Cookware for beautiful kitchen tools, cookware, and seriously fun “treat yourself” finds (it’s like shopping, but for your future meals).

You’ll also want to hit Shiloh Crossing, a newer shopping area with a ton of stores and restaurants—perfect for browsing when you want lots of options in one place. You might even find something special for your favorite sloth (me). I accept gifts.

Art, culture, and pretending you’re sophisticated

I’m a big fan of arts and culture—mostly because you can enjoy it while standing perfectly still (my strongest skill).

Start with the gallery of world-renowned artist Harry Koyama for breathtaking impressions of the American West (still waiting on my portrait… any day now). Then swing by the Yellowstone Art Museum for rotating exhibits and regional collections that make you feel fancy in a responsible way.

The Billings Brew Trail (my area of expertise)

If you read my post about the time Bert and I almost completed the Brew Trail, you already know I take this seriously. Many stops are conveniently clustered near downtown, making it easy to sip your way through the weekend without too much… you know… running.

In total, the trail includes breweries, distilleries, cider, and wine—plus plenty of good food along the way. Hydrate. I’m told that’s important.

And obviously… come see me

Last but certainly not least: you’ll want to visit me at ZooMontana, right? It’s the perfect wholesome stop to balance out the shopping bags and brew trail receipts.

Final Winston Notes

There you go—coffee, brunch, shopping, culture, craft beverages, and one extremely charming sloth. If your weekend turns out perfect, you’re welcome… and if it doesn’t, blame Uki and Roxy.