2026 Event Calendar
A visitor's month-by-month guide to the festivals, race weekends, and holiday events that shape the year.
The rest of the 2026 season — from the Saturday Farmers Market and the August Art-and-Wine weekend to the marquee Christmas Village block in December. Sourced from the Chamber calendar; race dates verified against live registration pages. (Events before July 20 have already run and have been removed from this calendar; see the archived recap for past coverage.)
Saturdays, June – September 2026
Best for: morning visitors · families · day-trippers from the valley
A weekly Saturday market in downtown Cloudcroft with fresh mountain produce, local honey, baked goods, and handmade crafts. The most reliable "every-weekend" event of the summer — easy to fold into any Saturday trip up the hill.
Full Farmers Market details →Saturday, August 1, 2026 · Registration 8:30 AM, meeting 10 AM · Cloudcroft High School gymnasium
Best for: OCEC members · locals · part-time residents
OCEC's annual member meeting comes to Cloudcroft, with giveaways, member updates, and lunch. A member-focused morning rather than a visitor draw, but worth knowing about if you're in town — expect extra activity around the school.
Saturday, August 1, 2026 · 3–5 PM · Noisy Water Winery, Cloudcroft
Best for: adults · wine tasters · low-key afternoon plans
A neo-indie folk set from Nova Rush, a Bent, NM–based vocalist and multi-instrumentalist whose songs lean relatable and story-driven. An easy afternoon pairing with a tasting flight before dinner.
August 7–9, 2026 · 10 AM – 5 PM · Sacramento Mountain Museum & Pioneer Village
Best for: adults · art shoppers · couples · repeat visitors
One of the strongest event weekends if you want Cloudcroft at its more polished and browse-friendly. It pairs naturally with galleries, shops, and slower in-town time. Info: Cloudcroft Chamber of Commerce, 575-682-2733 or chamber@coolcloudcroft.com.
Saturday, August 8, 2026 · 6–9 PM · Cloudcroft Brewing Company
Best for: adults · classic-rock crowds · Art & Wine weekenders
Classic rock at the brewery on the same weekend as Art and Wine in the Cool Pines — an easy evening cap after a day of browsing at the museum grounds.
Saturday, August 15, 2026 · 9 AM – 2 PM · Old Red Brick Schoolhouse Community Room (and north patio)
Best for: art shoppers · bargain hunters · morning browsers
Art supplies, art books, donated art, and yard-sale finds from the Cloudcroft Art Society. An easy morning stop on the busiest Saturday of the month — pair it with the Farmers Market before the afternoon crowds arrive.
Saturday, August 15, 2026 · 11 AM · Elevation Park
Best for: locals · community-minded visitors
Join the village in honoring the late Debbi McCurdy and her work fundraising for the new Native Air emergency helipad — a short, meaningful community ceremony in the middle of a full village Saturday.
Saturday, August 15, 2026 · Rim Trail (T105)
Best for: trail runners · race crews · strong outdoor travelers
One of the most serious athletic events on the calendar. The course runs the scenic Rim Trail (T105) at roughly 8,600 feet, with sweeping views of the Tularosa Basin. Four distances: 53K, 9.5 mile, 4.75 mile, and a 1-mile Kid's Dash. Even if you're not racing, it's a good weekend for people who like trail-running culture and an active town feel. Register at wanderlust.run.
Friday, August 21, 2026 · Rockabilly Strangers · 6–9 PM · Brewery Side · Saturday, August 22, 2026 · Christachio · 1–4 PM · Distillery Side
Best for: adults · live-music fans · weekend visitors
Back-to-back sets at the brewery: Rockabilly Strangers bring rockabilly energy to the Brewery Side on Friday evening, and Christachio plays a Saturday afternoon set on the Distillery Side. The brewery also runs karaoke every Monday (6–9 PM, Brewery Side) and family-friendly trivia every Wednesday (6–8 PM, Distillery Side).
Friday, August 28, 2026 · 7:45 PM · White Sands National Park · fees apply
Best for: day-trippers · photographers · couples · stargazers
Hike the dunes under a glowing full moon with a park ranger — one of the best down-the-mountain add-ons to a Cloudcroft trip. Tickets go on sale one month prior via Recreation.gov and sell out fast.
Saturday–Sunday, August 29–30, 2026
Best for: road cyclists · endurance riders · race crews
Scenic mountain rides ranging from 36 miles to 163 miles through the Sacramento Mountains — a big-ride weekend to close out August, with routes for strong recreational riders up to full gran-fondo distance. Register at BikeReg.
September 5–6, 2026
Best for: holiday-weekend visitors · families · easy festival weekends
One of the most practical event weekends because Labor Day already gives many people time to travel. Expect more town activity and less quiet than on a normal September weekend.
Saturday, September 19, 2026 · 33rd year
Best for: families · spectators · first-time visitors who want a Cloudcroft-specific scene
Free to watch, with arts, crafts, and food vendors on-site. Competitor registration begins at 8 AM, competition starts at 9 AM. Held at 1920 1/2 U.S. Highway 82. Contact: cloudcroftlumberjackday@gmail.com or 575-921-4737.
Full Lumberjack Day details →Sunday, September 20, 2026 · 10 AM start, downtown Cloudcroft
Best for: mountain bikers · racing crews · endurance-fitness travelers
Cloudcroft's storied XC mountain bike race — singletrack descents, rocky technical sections, and thin air at 8,676 feet. Three categories (Pro/Cat 1 · 17 mi, Cat 2/SS · 13.5 mi, Cat 3 · 10 mi), a $2,500 pro purse with equal payout for men and women, and a 175-rider cap that sold out the last two years. Falls the day after Lumberjack Day for a natural double-header weekend. Register at BikeReg.
Full race details →October 17, 2026
Best for: serious runners · ambitious outdoor visitors · shoulder season
The strongest October event we could verify. More specialized than the broad Chamber festival weekends, but a real draw if you like high-effort race events and cooler fall conditions.
October 2026 · exact date to be confirmed
Best for: adults · couples · craft-beer travelers · fall-foliage trips
The village's annual fall celebration — craft brews, German fare, and autumn mountain colors at one of the most scenic times of year in the Sacramento Mountains. October in Cloudcroft means cool air, turning leaves, and a perfect excuse to spend a day around the brewery.
Full Oktoberfest details →Fall 2026 · date TBA
Best for: families · Halloween-season visitors · costume crowd
Cloudcroft's family-friendly Halloween-season community event. The current-year date wasn't on the Chamber calendar at publication — confirm with the Chamber events page closer to fall.
November 27–28, 2026
Best for: holiday shoppers · families · early Christmas atmosphere
The cleanest late-November event on the Chamber calendar. A good fit if you want Cloudcroft leaning into holiday mode without waiting for mid-December.
December 11–19, 2026
Best for: families · holiday travelers · peak seasonal atmosphere
The marquee Christmas-period event block. If you want the strongest holiday feel in Cloudcroft, this is the one to plan around. Also one of the better reasons to book lodging early.
Full Christmas in Cloudcroft details →Not every weekend works for every traveler. These are the matches we'd start with based on who's coming and what kind of trip they want.
Labor Day Hoopla, Lumberjack Day, Mountain Christmas Village. Broadest Cloudcroft feel and the lowest barrier to entry.
Art and Wine in the Cool Pines, Christmas Market, Oktoberfest. Slower shopping, strolling, and dinner-centered weekends.
Labor Day Hoopla, Lumberjack Day, Mountain Christmas Village. The safest "there will be enough going on" answers.
Cloudcroft Ultra, Cloudcroft Gran Fondo, High Altitude Classic, Cactus to Cloud Sky Race. The clearest race-centered reasons to plan a trip.
Labor Day Hoopla and Oktoberfest. Festive town atmosphere without one specific crowd dominating the weekend.
Cloudcroft has live music — but it's not a nightly, city-style scene. The right way to think about it: shows turn up at a handful of venues, on event weekends, and in seasonal rotations. Lineups change often, so check close to your trip.
The strongest current live-music bet in town. August lineup: Designated Mind (classic rock) Saturday, August 8, 6–9 PM; Rockabilly Strangers Friday, August 21, 6–9 PM (Brewery Side); Christachio Saturday, August 22, 1–4 PM (Distillery Side). Weekly: karaoke every Monday 6–9 PM (Brewery Side) and family-friendly trivia every Wednesday 6–8 PM (Distillery Side). Instagram.
Cloudcroft Reader's summer guide grouped The Distillery with Cloudcroft Brewing as a regular live-music spot — one of the clearest local sources putting it on the repeat-music list.
Another likely music stop, especially for smaller live sets. Next up: Nova Rush (neo-indie folk) on Saturday, August 1, 3–5 PM. Gigtown profile.
Not a weekly music venue in the same way the brewery is, but local coverage shows the Lodge hosting music during special events — jamborees, lawn events, and Lodge-specific weekends.
Live music also shows up through the event calendar itself — art shows, festivals, and Pavilion-based weekends where music is part of the draw. Chamber events.
Music here is small-scale, close to the audience, tied to a venue that's also serving food or drinks, better on weekends than midweek, and more casual than ticketed-concert formal. If you want a big-headliner room, you're in the wrong town. If you want to sit outside with a drink and hear local or regional musicians on a low-pressure mountain evening, Cloudcroft fits well.
Pick a weekend that fits your trip and book early — the marquee weekends (Labor Day, Lumberjack Day / High Altitude Classic, Mountain Christmas Village) sell out lodging fast.