Checkerboard Bar & Inn MT

05/06/2026

Kailey Marie is back in Checkerboard. Sunday May 24th for Memorial Day. Be there or be Square!

05/05/2026

📍 New Listing in Checkerboard, Montana 📍

The Famous Checkerboard Bar & Inn is officially on the market.

Exceptional opportunity to own a fully operational bar situated on 2.39 acres in a high-traffic highway location. This established, turn-key business is ready for continued success, featuring a full liquor license, gambling endorsement, strong visibility, easy access, and ample on-site parking.

The property includes 7 rustic, dry, heated cabins—ideal for guests seeking a back-to-basics mountain retreat. A nearby shared bathhouse offers hot showers and restroom facilities for added convenience. Additionally, there are approximately 13 RV slips with 20- and 30-amp service available.

Located just 2.5 miles from Forest Service/BLM public access to Hunting District 452, the property is well-positioned for outdoor enthusiasts. Also conveniently located 47 miles from Showdown Ski Area and 22 miles from White Sulphur Springs, known for its natural hot springs.

💰 $475,000

📞 Cale Updegrave (406) 901-0422

📞 Stacy Olson (406) 350-0621

05/05/2026

Montana Huckleberry Drinks At Checkerboard!

04/05/2026

04/03/2026

Brenda is back!!! come see her Fridays, Saturdays & Sundays.

03/26/2026

We’re Open This weekend. See you soon

03/19/2026

We apologize the old beer cooler finally decided to retire itself. The new ones ordered and hopefully will be here by next weekend.

03/13/2026

See Ya Tomorrow!!!

03/06/2026

Friends In High Places….