High Times Cannabis Cup Debuts in Montana

HELENA – A competition that helped define American Cannabis culture is coming to a new state. Big Sky Country is preparing for its first-ever High Times Cannabis Cup.

The event is set for Saturday, September 5, at The Pub Station in Billings – a six-hour celebration of live music, vendor activations, food trucks, live glass blowing, and a community-judged awards ceremony crowning the best Cannabis products in the state.

It’s been just over a year since Josh Kesselman, founder of RAW Rolling Papers, purchased High Times and its associated assets out of receivership for $3.5 million alongside former co-owner Matt Stang. Since then, Kesselman has invested an additional $1.85 million in the revival, relaunching the print magazine in collectible editions, rebuilding the website, and most importantly, restoring the Cannabis Cup circuit, starting with New York and New Jersey before now turning toward Montana.

Billings was chosen for a market that has earned the attention. Since adult-use sales opened on January 1, 2022, Montana retailers have generated over $1 billion in cumulative Cannabis revenue, with monthly sales reaching $27.3 million by year-end 2025 – a 13% increase from where the market started. Adult-use now represents about 90% of all purchases. The state also carries one of the highest dispensary-per-capita densities in the country, with 557 licensed retail locations serving roughly 1.1 million residents.

The Cup’s format remains its trademark. Rather than a panel of industry judges, everyday consumers do the scoring. Categories span eleven product types:

• indica, sativa, and hybrid flower,
• standard and infused pre-rolls,
• solvent and solventless concentrates,
• vape cartridges, and
• two edibles brackets.

Judges score products through a digital portal.
Results are unveiled live on September 5.

The awards show carries the working billing “The Oscars of Weed.” Headlining the stage is Bumpin Uglies, joined by Montana native Austin Martin, the Cannabis Cup Band, and special guest Josh David Barrett of The Wailers. Kesselman will be there in person. Tickets are priced at $21 for registered judges, $42 for general admission, and $100 for VIP, with all attendees required to be 21-plus.

What the Montana Cannabis Cup represents, in practical terms, is a community-facing validation mechanism arriving in a market that has grown faster than its cultural infrastructure. Montana’s operators have had no nationally recognized, consumer-judged benchmark. Now that gap has real commercial implications for branding, shelf placement, and consumer loyalty. The High Times Cannabis Cup fills it. For Kesselman, a Billings datestamp on the calendar is also proof of geographic momentum. Along with media presence, the Cup revival is building a real circuit. Whether this becomes an annual fixture in Montana will depend on turnout and industry uptake, but the first edition gives the state’s Cannabis community something it has not had before – a stage that is entirely its own.