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✌️ The Weekend Drop | This Weekend in Cheyenne

✌️ The Weekend Drop | This Weekend in Cheyenne

A look at events happening in Cheyenne this weekend.

May 21, 2026

First Look

On the Radar This Weekend

Start the weekend with MOM’s UNHINGED - Comea Comedy Night at The Metropolitan, where motherhood meets stand-up and proceeds support CLIMB Wyoming. On Saturday, browse plants, garden finds, and local vendors at the 6th Annual Outdoor Plant Sale, then wind down with Live Music: Jessica Herring at The Blue Stem Wine House. Slow things down on Sunday with Paint & Prayer with Flydragon Design Art Studio. Enjoy your Memorial Day weekend and see you out there.

The Legend Dinner Club

Dinner Club Is Back

The first Legend Dinner Club has wrapped, and the reviews are in. Attendees came in not totally knowing what to expect and left already talking about doing it again.

“Great meeting new people I wouldn’t normally meet. Conversation flowed easily. We all plan on doing it again!”

“The people at the table were really nice and I enjoyed meeting them. I had a good time filled with laughter and good vibes. What a good idea!”

“It was easy to talk to the people at my table. Everyone seemed open and kind.”

Seats are already being claimed for the next one on Wednesday, June 10. Grab your seat, take the quiz, and we’ll handle the logistics.

Save Your Seat

Next dinner: Wednesday, June 10 · Spots are limited

FRIDAY, MAY 22nd

COMEA Parking Lot Sale | 9:00 a.m. | COMEA House and Resource Center, 1421 W Lincolnway | Free to Attend | COMEA’s parking lot sale is back for one day with clothing, household items, furniture, tools, and more.

Cheyenne Gaming Convention 2026 (Also Sat & Sun) | 1:00 p.m. | Red Lion Hotel & Conference Center, 204 W Fox Farm Rd | Varies | Game tables, vendors, tournaments, and more return for a full weekend of tabletop fun.

Beer and Bread Pairing | 5:00 p.m. | Black Tooth Brewery, 520 W 19th St | Free to Attend | Rustic Pantry brings the baked goods to Black Tooth for a happy hour pairing of craft beer, beer-infused breads, and pastries available for purchase.

Live Music: Davis and Maverick | 6:00 p.m. | Black Tooth Brewery, 520 W 19th St | Free to Attend | Davis and Maverick bring the soundtrack to Friday night with cold beer and live tunes.

MOM’s UNHINGED - Comea Comedy Night | 7:00 p.m. | The Metropolitan Downtown, 1701 Carey Ave | $30 | Get ready to laugh with these comedians who discuss the ups and downs of motherhood in an unapologetic way, with proceeds supporting CLIMB Wyoming.

Legally Blonde The Musical Also Sat & Sun | 7:00 p.m. | Mary Godfrey Playhouse, 2706 E Pershing Blvd | $21+ | Elle Woods takes the stage to kick off the second weekend of the show.

Live Music: Winston Creek | 9:00 p.m. | Horse Palace Swan Ranch, 5640 High Plains Rd | Free to Attend | Catch this Laramie band for a late-night live set of live music.

Saturday, MAY 23rd

6th Annual Outdoor Plant Sale | 9:00 a.m. | Ashley Furniture Parking Lot , 3151 Nationway | Free to Attend | This small garden market features 25+ vendors with plants, plant accessories and more.

Live Music: Jordan Hoff | 6:00 p.m. | Black Tooth Brewery, 520 W 19th St | Free to Attend | Jordan Hoff takes over the taproom for a laid-back live set.

Plant Bingo & Beer | 6:00 p.m. | Freedom’s Edge Brewing Company, 1509 Pioneer Ave | $38.12 | Red Sage Apothecary and Freedom’s Edge team up for bingo, good beer, and a chance to win plants while you play.

Live Music: Jessica Herring | 7:00 p.m. | The Blue Stem Wine House, 1909 Warren Ave | Free to Attend | Jessica makes her Blue Stem debut with a mix of your favorite songs.

Live Music: Eric Golden | 9:00 p.m. | Horse Palace Swan Ranch, 5640 High Plains Rd | Free to Attend | Eric performs a late-night set of honky-tonk county.