What’s Happening in Vail: October & November 2025

liliaasenova
Sep 30, 2025
3 min read

Colorful autumn trees in foreground with snow-capped mountains and a pine forest under a dramatic purple and pink sky.

Even before the lifts start spinning, Vail hums with energy in the fall. October and November bring a blend of arts, family fun, music, and the highly anticipated mountain opening. Here’s your guide to what’s happening:

Early October: Arts, Markets, and Sports

Cindy Eskwith Memorial Vail Cup Soccer (Oct 3–5 | All Day)
A weekend-long celebration of soccer bringing teams from across the region.
Handmade in Colorado Expo (Oct 3 & 4 | 11:00 am – 6:00 pm)
Local artisans showcase jewelry, art, crafts, and more—a great way to take home a piece of Colorado creativity.
The Last Vail Farmers’ Market & Art Show (Oct 5 | 9:30 am – 3:00 pm)
Don’t miss the final chance of the year to stroll through the market, enjoy gourmet bites, and shop for unique gifts.
Discover Vail Art Series: Glass Etching (Oct 9 | 5:30 pm – 7:00 pm)

An intimate hands-on class where participants create their own etched glass designs.

Where to stay & dine: Consider staying at The Sebastian or Sonnenalp, both just steps from Vail Village for easy access. For dinner after a day of exploring, treat yourself to Sweet Basil, one of Vail’s most celebrated restaurants.

Mid October: Thoughtful Conversations and Live Performances

Ethical Leadership Forum (Oct 9–10 | All Day)
Leaders and thinkers gather to explore the role of ethics in modern business and society.
Good Music For a Good Mynd (Oct 11–12 | 1:00 pm – 7:00 pm)
Two days of uplifting performances merging music and wellness.

Halloween-themed porch with jack-o'-lanterns, black balloons, and orange string lights. Autumn leaves cover the ground, creating a festive mood.

Halloween in the Mountains

The Rocky Horror Show | VVTC (Oct 29–Nov 1 | 8:00 pm)
A Vail Valley Theatre Company tradition—costumes, music, and the ultimate cult classic live on stage.
Trick or Treat Trot (Oct 31 | 2:00 pm)
Families are invited to dress up and trick-or-treat through Vail Village in this festive Halloween tradition.

Where to stay & dine: Families will love Four Seasons Vail or Ritz-Carlton, Bachelor Gulch, both offering kid-friendly amenities. Afterward, keep it casual with pizza night at Blue Moose Pizza, always a hit with children in costume.

November: Kicking Off the Winter Season

Vail Mountain Opening Day (Nov 14 | All Day)
The moment skiers and snowboarders wait for all year—the official opening of Vail Mountain. Get ready to make your first turns of the season.

Where to stay & dine: Go for ski-in/ski-out convenience at The Ritz-Carlton, Bachelor Gulch or the lively atmosphere of The Hythe Vail. Toast the season with cocktails at Remedy Bar at the Four Seasons.

Ski lift viewed from below against a clear blue sky, with skiers' legs and skis visible, featuring black and orange gear.

Vail Après | Stoke Sessions (Nov 14, 21, 28 | 4:00 pm – 7:00 pm)
Après-ski comes alive with live music and community gatherings at the base of Gondola One.
CRAWL 4 ALS: Pub Crawl Challenge (Nov 15 | 5:00 pm)
Drink for a cause while joining this lively fundraiser through Vail’s bars and restaurants.
Silent Disco (Nov 19 & 26 | 3:30 pm – 6:30 pm)
Dance like nobody’s watching with headphones and beats under the alpine sky.
Discover Vail Art Series: Wine & Stein Glass Painting (Nov 19 | 5:00 pm – 6:30 pm)
A cozy evening combining art, wine, and hands-on creativity.
Ice Skating Shows (Nov 29 | 4:45 pm – 5:30 pm)
Watch dazzling performances on the ice in Vail Square.
Lionshead Tree Lighting (Nov 29 | 6:00 pm)
Usher in the holiday season with music, lights, and cheer in Lionshead.

Where to stay & dine: For November’s mix of après and nightlife, Sonnenalp and The Sebastian keep you close to the action. Before heading to a silent disco or après session, enjoy hearty alpine cuisine at Mountain Standard.

Vail: October & November

From soccer cups and art shows to mountain openings and holiday lights, fall in Vail is brimming with energy. Whether you’re planning a family trip, a romantic getaway, or an early ski-season kickoff, pairing the right hotel and dining with these events makes the experience even more memorable.

No matter which event draws you to Vail this fall, we’d be honored to be part of your journey. Whether you’re traveling with friends, family, or a group, our private SUVs and luxury vans make it easy to relax and focus on the fun. See you in Vail this October and November!