The Biggest Weekend of the Fall
Labor Day weekend is when Cloudcroft packs the most into three days. Zenith Park anchors it all — the Hoopla, a craft show ringed with food trucks, tournament pickleball on the public courts, and a Sunday car show — while the Old Red Brick Schoolhouse hosts the Cloudcroft Art Society’s annual art show and the CLOC Pavilion stages a classic melodrama each evening.
Nearly everything is walkable from the village center, most of it is free, and the crowd is a mix of valley day-trippers, holiday travelers, and locals. If you want Cloudcroft at its liveliest, this is the weekend.
Seven Events, Three Days
Everything happening September 4–6, 2026, sourced from the Village of Cloudcroft and event organizers.
Mountain Smash Pickleball
The Cloudcroft Mountain Smash tournament, a fundraiser for Cloudcroft Track & Field, on the Zenith Park public courts.
Heritage Day Car Show
Classics, hot rods, and motorized arrivals of every kind at Zenith Park, with Best in Show, 2nd, and 3rd place awards.
Farmers Market at the Ice Rink
The summer-weekend market runs right through the holiday at the Cloudcroft Ice Rink in the heart of Zenith Park — locally grown and baked goods, freeze-dried fruits and candies, and local honey. Cash only.
Make it a double-header month. Lumberjack Day (Sept 19) and the High Altitude Classic mountain bike race (Sept 20) land two weekends later — see the full 2026 calendar.
Visiting on Labor Day Weekend
Practical info for the busiest weekend of the fall.
Where
Zenith Park hosts most of it; the Art Society show is at the Old Red Brick Schoolhouse. Everything is walkable from Burro Avenue.
Lodging
Holiday weekends sell out Cloudcroft lodging early — book as far ahead as you can. See the full lodging guide.
What to Bring
Layers — early September at 8,676 feet is warm in the sun and cool in the shade, with afternoon storms possible. Cash helps at vendor booths.
Good to Know
Expect the village at full capacity: parking fills near Zenith Park, and restaurants run waits at peak hours. Arrive early and walk where you can.
More 2026 Events in Cloudcroft
Pair Labor Day weekend with the rest of Cloudcroft’s 2026 calendar of festivals and race weekends.