2026 Event Calendar

The Top Events in Cloudcroft

A visitor's month-by-month guide to the festivals, race weekends, and holiday events that shape the year.

▲ 8,676 ft ★ 8 marquee weekends left Now → December

On This Page

01 — The Calendar

Cloudcroft 2026, Month by Month

The rest of the 2026 season — from October’s Halloween-week lineup to the marquee Christmas Village in December. Sourced from the Chamber calendar; race dates verified against live registration pages. (Events that have already run are removed from this calendar.)

2nd Mon

A paint class holding up their finished cactus canvases at the Noisy Water Winery tasting room in Cloudcroft

Sip & Paint at Noisy Water Winery

Every second Monday · 6:00 – 8:00 PM · next: Monday, October 12 · Cloudcroft Tasting Room, 505 Burro Ave

Best for: adults · date nights · first-time painters

Unleash your creative side at this fun, instructor-led paint night — no experience needed. The ticket includes one glass of wine ($15 or less), beer, cider, or any non-alcoholic beverage, plus everything you need for an evening of art and good company.

October

October Live Music at Cloudcroft Brewing Co. & The Distillery

All month · evening sets 6–9 PM, afternoon sets 1–4 PM · 1301 Burro Ave

Best for: adults · live-music fans · weekend visitors

A full October calendar across both rooms: Rosewater Blues (Oct 2), the Oktoberfest lineup (Oct 3), Burnstein & Andes Duo (Oct 9), Dynamic Duo and Sons of Soul (Oct 10), Todays Time Traveler (Oct 11), Doso Dirtbags (Oct 12), I Am Hologram (Oct 16), Spivey and Chris Baker (Oct 17), Trick Myers (Oct 23), Damian Luna and Catfish Fry (Oct 24), Benny Bassett (Oct 30), and a Halloween double bill of Christachio and the Rockabilly Strangers (Oct 31). Plus karaoke every Monday 6–9 PM and trivia every Wednesday 6–8 PM at The Distillery.

Oct 9–31

Haunted Village

October 9, 10, 16, 17, 23, 24, 30 & 31, 2026 · 7–10 PM · Sacramento Mountains Historical Museum & Pioneer Village, 1000 Hwy 82

Best for: families · Halloween-season visitors · costume crowd

Cloudcroft's family-friendly Halloween-season event returns for four weekends of after-dark fun at the Pioneer Village. $15 admission — this is the museum's biggest fundraiser of the year. Info: 575-682-2932.

Oct 17–18

Cactus to Cloud Sky Race

October 17–18, 2026 · Oliver Lee State Park to Cloudcroft

Photo: Travis McWhorter, courtesy of Wanderlust Running

Best for: serious runners · ambitious outdoor visitors · shoulder season

The strongest October event we could verify. The point-to-point course starts at Oliver Lee State Park and climbs to Cloudcroft — the 50K Sky Run goes off at 6:30 AM and the 32K Cloud Run at 8:00 AM on Saturday. Registration closes October 11 on UltraSignup.

Oct 18

Yoga in the Clouds at Noisy Water Winery

Sunday, October 18, 2026 · 6:00 – 7:00 PM · Cloudcroft Tasting Room, 505 Burro Ave

Best for: adults · wellness travelers · winding down a village weekend

A one-hour, all-levels evening yoga flow at the tasting room — bring your own mat. The ticket includes a glass of wine (up to $15) or a non-alcoholic drink afterward.

Oct 23

Wine 102 at Noisy Water Winery

Friday, October 23, 2026 · 6:00 – 8:00 PM · Cloudcroft Tasting Room, 505 Burro Ave

Best for: adults · wine-curious visitors · date nights

A guided tasting experience — no flashcards, no intimidating tasting notes, no pressure to be right. Learn to identify what’s happening on your palate and why certain varietals speak to you, whether you’re building on Wine 101 or just ready to go a little deeper.

Oct 24

5K Trick or Trot & Fun Run

Saturday, October 24, 2026 · 9:00 AM · Zenith Park

Best for: families · runners · costume lovers

A Halloween costume run benefiting the Cloudcroft Schools Technology Student Association — come in costume and race the 5K ($50) or the fun run ($20), with free t-shirts for all participants. Prizes for finishers in each age group, plus best overall, scariest, best homemade, and most creative costume.

Oct 25

Scary Movie Night at Noisy Water Winery

Sunday, October 25, 2026 · 7:00 – 9:00 PM · Cloudcroft Tasting Room, 505 Burro Ave

Best for: adults · Halloween fans · trivia players

A Halloween movie night with a twist — clues hidden in the film may lead to answers in a Halloween trivia game. Halloween slushies, wine, beer, and non-alcoholic drinks available for purchase, and movie-goers are welcome to bring their own snacks.

Oct 30

Cloudcroft Schools Fall Festival

Friday, October 30, 2026 · 5:00–7:30 PM · Middle School Commons & Gym

Best for: families · kids · community supporters

Carnival games, a bouncy house, bingo, raffles, and a cakewalk — a fundraiser for Cloudcroft Schools, and an easy family kickoff to Halloween weekend.

Oct 30

Spooky Charcuterie Building Class at Noisy Water Winery

Friday, October 30, 2026 · 6:00 – 8:00 PM · Cloudcroft Tasting Room, 505 Burro Ave

Best for: adults · hands-on creatives · Halloween-weekend visitors

Build a Halloween-themed charcuterie board to take home — boards and fixings provided, no experience needed. The ticket includes one glass of wine ($15 or less).

Oct 30–31

Pumpkin Roll & Halloween Weekend

October 30–31, 2026 · Swallow Place, Burro Avenue & Zenith Park

Best for: families · costume crowd · fall-color stragglers

The village's Halloween send-off: the Pumpkin Roll goes at 11 AM Saturday down Swallow Place from the Michael Nivison Public Library (90 Swallow Place) — age groups from kids 1–5 up to adults — and the costume parade follows at 1 PM down Burro Avenue, with shops open for trick-or-treating. The Schools Fall Festival (Friday) and the James Sewell Ice Rink grand opening (Saturday) each have their own listings on this page.

Oct 31

James Sewell Ice Rink Grand Opening

Saturday, October 31, 2026 · Noon–10 PM · Zenith Park

Best for: families · skaters · Halloween-weekend visitors

The ice rink opens for the season with a full day of skating, face painting, a costume contest, trunk-or-treat, and giveaways — right in the middle of Halloween weekend at Zenith Park.

Oct 31

Fall Festival at Summit Christian Fellowship

Saturday, October 31, 2026 · 1 PM · Burro Avenue

Best for: families · kids · trick-or-treaters

Games, food, prizes, and a bounce house on Burro Avenue — one more family-friendly stop on Cloudcroft’s packed Halloween Saturday.

Nov 6

2nd Annual Cloudcroft Makes Art! Open Art Show

Friday, November 6, 2026 · 5–7 PM · Michael Nivison Public Library, 90 Swallow Place

Best for: local artists · families · art lovers of every age

A juried community art show at the library, open to everyone. Two categories (Amateur and Professional) and three age groups (Youth 1–10, Young Adult 11–18, Adult 18+), with prizes for the top entry in each and Best in Show. All media are welcome; entries must be no larger than 2′ by 2′ including the frame, up to three per artist. Bring entries to the library by Wednesday, October 28, and pick up pieces by Wednesday, November 11, or they become a donation to the library’s walls.

Nov27–28

Christmas Market

November 27–28, 2026

Best for: holiday shoppers · families · early Christmas atmosphere

Get ready to load up on stocking stuffers and more at this local market. A good fit if you want Cloudcroft leaning into holiday mode without waiting for mid-December.

Nov/Dec

Crowd circled around the tall UllrFest bonfire at night at Zenith Park in Cloudcroft

UllrFest at Zenith Park

Late November / early December 2026 · date TBA · Zenith Park

Best for: locals-at-heart · ski-season optimists · bonfire people

The village's annual snow-summoning ritual — a bonfire at Zenith Park where old skis are burned as an offering to Ullr, and everyone hopes the season answers. Date to be announced; check back or watch the Chamber calendar.

Dec 5

Runners in Santa suits and holiday sweaters heading out from the start of the Cloudcroft Ugly Sweater 5K

Ugly Sweater 5K Run & 1 Mile Walk

Saturday, December 5, 2026 · 5K 4:00 PM · 1-mile walk 4:05 PM · Cloudcroft Pavilion, 1100 James Canyon Hwy

Best for: runners · families · anyone with a truly regrettable sweater

Cloudcroft's holiday-season race — a 5K run and a one-mile walk, ugly sweaters strongly encouraged — the field is limited to 100 participants. Register at Race Roster.

Dec11–19

Santa and Mrs. Claus waving from a vintage red fire truck beside the lit Christmas tree in downtown Cloudcroft

Mountain Christmas Village

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 →

02 — Editor's Picks

Best Event Weekends by Visitor Type

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.

First-Time Visitors

Lumberjack Day and Mountain Christmas Village. Broadest Cloudcroft feel and the lowest barrier to entry.

Couples

Christmas Market and Mountain Christmas Village. Slower shopping, strolling, and dinner-centered weekends.

Families

Lumberjack Day and Mountain Christmas Village. The safest "there will be enough going on" answers.

Runners & Riders

Cloudcroft Gran Fondo, High Altitude Classic, Cactus to Cloud Sky Race. The clearest race-centered reasons to plan a trip.

Town Lively, Not Niche

Lumberjack Day. Festive town atmosphere without one specific crowd dominating the weekend.

03 — After Dinner

Where to Find Live Music in Cloudcroft

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.

Cloudcroft Brewing Company

The strongest current live-music bet in town. Weekly: karaoke every Monday 6–9 PM (Brewery Side) and family-friendly trivia every Wednesday 6–8 PM (Distillery Side). Instagram.

The Distillery

The Distillery Side of Cloudcroft Brewing — same roof, same address (1301 Burro Ave) — hosts the Wednesday trivia night and many of the calendar's afternoon sets. Cloudcroft Reader's summer guide lists it as a regular live-music spot.

Noisy Water Winery Cloudcroft

Another likely music stop, especially for smaller live sets. The tasting room also hosts an instructor-led Sip & Paint night every second Monday at 6 PM. Gigtown profile.

The Lodge at Cloudcroft

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.

Chamber & festival 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.

04 — Event Archive

Earlier in 2026 — Already Happened

These 2026 events have already run and are kept for reference — most return every year. Nothing in this section is upcoming; the current calendar is at the top of the page.

Oct 10

Bucket Golf Tournament

October 10, 2026 · Elevation Park · this event has passed

Best for: families · casual golfers · locals-weekend visitors

A fundraiser for Cloudcroft Village Parks and Recreation at Elevation Park. To play or sponsor, ask for Bri Jonnes at High Altitude on Burro Avenue. Magick Melts, the fantasy-themed food truck from High Rolls Mountain Park, will be on site with its grilled sandwiches — look for the Alchemy Melt and Enchanted Panini — and edible-glitter Swedish crème for dessert.

Oct 6

Trivia Night at Noisy Water Winery

Tuesday, October 6, 2026 · 6:30 – 8:00 PM · Cloudcroft Tasting Room, 505 Burro Ave · this event has passed

Best for: adults · trivia teams · weeknight visitors

An evening of team trivia at the Noisy Water tasting room — bring friends or join a table, with wine, beer, and non-alcoholic drinks available by the glass.

Oct 3–4

Oktoberfest Weekend in Timberon

Saturday–Sunday, October 3–4, 2026 · High Country Lounge & Grill, Timberon · this event has passed

Best for: adults · day-trippers · back-road explorers

Timberon's High Country Lounge & Grill celebrates Oktoberfest in the mountains: an authentic German schnitzel special with pickled cabbage and spaetzle (peach cobbler for dessert), homemade pretzels with beer cheese, and brats all weekend. Saturday brings a cornhole tournament (2–5 PM), beer stein relay race (6 PM), stein-holding contest (7 PM), and Hammerschlagen (7:30 PM), with a karaoke party after — and a meal discount if you show up in your best lederhosen or dirndl.

Oct 3

Competitors holding beer steins at arm's length during the stein-holding competition on the Cloudcroft Brewing Company patio

Oktoberfest at Cloudcroft Brewing Co. & The Distillery

Saturday, October 3, 2026 · from noon · 1301 Burro Ave · this event has passed

Best for: adults · live-music fans · fall-weekend visitors

A full afternoon and evening of Oktoberfest: live music from the Borderless Brass Band (1–4 PM), Dale Young at The Distillery (4–6 PM), and the Doso Dirtbags (6–9 PM). Brat plates from noon until sold out, and a beer stein-holding competition from 2–4 PM.

Jun–Sep

Cloudcroft Farmers Market

Summer weekends · Fridays 5 PM & Sundays 9 AM · Cloudcroft Ice Rink, Zenith Park · cash only · this event has passed

Best for: weekend visitors · families · day-trippers from the valley

A community market at the Cloudcroft Ice Rink in the heart of Zenith Park — locally grown and baked goods, freeze-dried fruits and candies, and local honey. The most reliable "every-weekend" event of the summer, and cash only, so hit the ATM first.

Full Farmers Market details →

Sep 29

Alcohol Ink Painting at Noisy Water Winery

Tuesday, September 29, 2026 · 6:00 – 8:00 PM · Cloudcroft Tasting Room, 505 Burro Ave · this event has passed

Best for: adults · date nights · hands-on creatives

Turn a plain tile into a one-of-a-kind piece at this guided evening of alcohol ink painting — tiles and rubbing alcohol provided, no experience needed, and the ticket includes a glass of wine (up to $15). Seats are limited.

Sep24–27

Fair-goers on a spinning carnival ride at sunset on the midway at the Otero County Fair

Otero County Fair and Rodeo

September 24–27, 2026 · 401 Fairgrounds Road, Alamogordo · this event has passed

Best for: families · rodeo fans · down-the-mountain day trips

The county's classic fair-and-rodeo week, about 35 minutes down the hill in Alamogordo — livestock, carnival, and rodeo nights. An easy add-on to a late-September Cloudcroft stay. More: oterocountyfair.com.

Young exhibitors leading their sheep around the show ring under the Otero County Fair sign

Sep 20

Yoga in the Clouds at Noisy Water Winery

Sunday, September 20, 2026 · 6:00 – 7:00 PM · Cloudcroft Tasting Room, 505 Burro Ave · this event has passed

Best for: adults · wellness travelers · winding down a busy village weekend

A monthly evening of movement and relaxation at the Noisy Water tasting room — local instructor Beth Merrell leads a one-hour, all-levels yoga flow, and the ticket includes a glass of wine (up to $15) or a non-alcoholic beverage afterward. Bring your own mat. Falls the evening after the Lumberjack Day / High Altitude Classic weekend — a well-timed reset.

Sep 20

High Altitude Classic Mountain Bike Race

Sunday, September 20, 2026 · 10 AM start at the High Altitude shop, downtown Cloudcroft · awards 2 PM at Elevation Park · this event has passed

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) 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 →

Sep 19

Lumberjack Day

Saturday, September 19, 2026 · 33rd year · this event has passed

Best for: families · spectators · first-time visitors who want a Cloudcroft-specific scene

Free admission, with food, craft vendors, family fun, and a kids halftime show. Held at Ski Cloudcroft, 1920 U.S. Hwy. 82. Competitor registration begins at 8 AM, competition starts at 9 AM — $10 per event, with cash payouts for 1st, 2nd, and 3rd place. More: cloudcroftlumberjackday.com, cloudcroftlumberjackday@gmail.com or 575-921-4737.

Full Lumberjack Day details →

Sep18–19

Four actors on stage in front of the Hanover D. Cash Medical Clinic set at a Cloudcroft Light Opera Company melodrama

CLOC Melodrama: "The Inventor's Daughter"

September 18 & 19, 2026 · 7:30 PM · CLOC Pavilion, Zenith Park · free admission · this event has passed

Best for: families · theater fans · evening plans after a festival day

The Cloudcroft Light Opera Company stages "The Inventor's Daughter, or... The Villain Made a Grab for the Lab" — classic boo-the-villain melodrama under the pavilion. Free to attend, and an easy evening cap on Lumberjack Day weekend.

Sep 4–6

Labor Day in Cloudcroft

September 4–6, 2026 · this event has passed

The Hoopla, Heritage Day Car Show, Mountain Smash pickleball, Battle of the Food Trucks & Craft Show, the Art Society show, and the CLOC melodrama — the village's big fall kickoff weekend.

Sep 4–6

Labor Day Live Music at Cloudcroft Brewing Company

September 4–6, 2026 · this event has passed

Doso Dirtbags, Christachio, and The Ghetto Vaqueros over the holiday weekend, plus The Lodge's Labor Day BBQ.

Aug29–30

Cloudcroft Gran Fondo

August 29–30, 2026 · this event has passed

Scenic mountain rides from 36 miles to a 163-mile gran fondo through the Sacramento Mountains.

Aug 28

Moonlight Hike at White Sands National Park

August 28, 2026 · this event has passed

Ranger-led full-moon hike on the gypsum dunes — the classic down-the-mountain add-on. Runs on full-moon dates through the season via Recreation.gov.

Plan Your Event Weekend

Pick a weekend that fits your trip and book early — the marquee weekends (Lumberjack Day / High Altitude Classic, Mountain Christmas Village) sell out lodging fast.

Find Lodging Complete Cloudcroft Guide