A Couples Guide to 24 Hours in Helena, Montana

I (Alli) learned my state capitals by singing a catchy little tune that I learned in elementary school (anyone else?) - and it still comes in handy to this day! (Name the capital of Alabama… Montgomery! Boom!!) 

When I heard we were stopping in Helena, Montana, that song immediately came to mind. And I of course, began singing it to Bobby. ;) But beyond the fact that Helena is indeed Montana’s state capital, my knowledge about this city was limited! Thankfully that changed on our roadtrip, as we spent some time exploring this booming, history and outdoorsy city. And it only took 24 hours for us to know we want to go back. We have a feeling you’ll feel the same way, too.


Hike the 1906 Trail :: We love a good early morning hike, and this 2.9 mile loop is not only very easy (and dog friendly), but it takes you to the top of Mt. Helena, where you’ll find stunning views of the capitol city. Bring water, the hike is gradual, but it IS uphill!

Light Breakfast at HUB Coffee :: Grab a cappuccino and a breakfast sandwich at HUB Coffee, a bright, airy, and welcoming coffee shop right in the heart of Helena’s Downtown Walking Mall. If you feel like a sweet treat, try one of their delectable baked goods. Hey, you’re on vacation!

Explore the Downtown Walking Mall :: There are plenty of fun shops, boutiques, restaurants, and bars throughout the Walking Mall or “Last Chance Gulch” for one to discover. Be sure to stop in The Parrot Confectionery - a quaint old fashioned candy store!

Top of the 1906 Trail!

Sally loved the 1906 trail :)

Outdoor walking mall views!


Lunch at Windbag Saloon :: You’ll probably be surprised to find out that this modern and lively pub sits in what was Helena’s last bordello! Now, the Windbag Saloon serves some of the best bar food and drinks in town. Don’t leave without trying their mac n’ cheese!

Cathedral of St. Helena :: Modeled after the Votivkirche in Vienna, Austria, this jaw-dropping cathedral rivals European Cathedrals, with its stunning stained glass windows and intricate architecture. If you’re lucky, you may even hear the organ play!

Mac n’ cheese at Windbag!


Burgers at The Friendly York Bar :: Just a short (and scenic) 20 minute drive from downtown Helena is this rustic, hole-in-the-wall, remote bar. While their drinks are good (and cheap), the star of the show here is their burger. Grab a seat at the bar, order a famous York burger and a cold one, and make friends with the locals!

Wine at The Hawthorne :: End the night with a crisp glass of wine - and maybe a cheese board if you’re still hungry - at this chic bottle shop and tasting room. It’s intimate and romantic, and their selection of wine is really impressive. Don’t be afraid to ask questions, the servers are incredibly knowledgeable and helpful!

24 hours in Helena, Montana isn’t enough. But if you stick to this itinerary, you’ll get a great taste for all that this entrancing city has to offer. And you’ll definitely leave anxious to plan your next trip back!