Fall in the Vail Valley + the Events That Define the Season

Fall doesn’t rush into Vail—it eases in.

One day the trails are still warm from summer sun, and the next you’re noticing the first tips of gold in the aspens. By mid-September, the mountain feels different. Lighter. Slower.

Locals call it shoulder season, but for those who know Vail beyond the headlines, it’s actually a favorite time to be here. The pace shifts. The trails quiet. The rhythm of the valley feels more personal.

Fall isn’t a break—it’s a reset.

And these upcoming events reflect exactly that:

Beaver Creek Oktoberfest

August 29–31, 2025 | Beaver Creek Village

An early kickoff to the season that blends mountain charm, festive music, and relaxed community fun. A great lead-in to fall’s quieter moments. Learn More

Lionshead Oktoberfest

September 5–7, 2025 | Lionshead Village

A spirited celebration to mark the change in seasons with a local, casual feel. Raise a stein, toast the turning leaves, and enjoy a moment that’s been a staple of fall in the valley for decades.  Learn More

The Colorado Grand®

September 8–13, 2025 | Passes Through Vail

This invitation-only 1,000-mile vintage road rally features rare pre-1960 sports cars winding through Colorado’s most scenic routes—including Vail. It draws collectors, entrepreneurs, and legacy families who understand that the most meaningful journeys are never rushed.  Learn More

Vail Oktoberfest – Vail Village

September 12–14, 2025 | Vail Village

The second weekend of Oktoberfest brings even more energy to the village, pairing culinary highlights with Bavarian traditions, music, and mountain hospitality. Learn More

Bravo! Vail – Final Concerts

Through Early October 2025 | Ford Amphitheater

These final performances offer a soft landing to summer, with orchestras playing against the backdrop of crisp air and golden trees. It’s the kind of concert you feel as much as you hear.

Learn More

Vail Farmers’ Market Finale

Through October 5, 2025 | Meadow Drive

The final few Sundays are a favorite for locals and returning homeowners alike. Warm pastries, hand-thrown pottery, and a slower pace—just as the leaves begin to peak.  Learn More

Polar Plunge & 5K – Avon

October 25, 2025 | Nottingham Lake

Bold, playful, and for a good cause, this community tradition invites you to take a quick dip and share a laugh before warming up lakeside with neighbors and friends.

Avon Turkey Trot

November 27, 2025 | Thanksgiving Morning

This laid-back 5K brings out multi-gen families and seasonal regulars. It’s the kind of morning that feels familiar and rooted—just like fall in the valley.

If you have experienced fall in Vail, you already know—it’s not the off-season. It’s when this place becomes something even more special.

In Fall 2026 the Vail Village rhythm will include something new:

A fire-lit gathering after an evening concert.

A quiet reconnection after the morning market.

A space that feels like a natural extension of your Vail life.

Opening Summer 2026, THE SIXTY TWO™ Society is being built for just that.

Rooted in legacy. Designed for connection. Created for those who already know this valley by heart, or desire to.

A limited number of Founder’s Circle Memberships are  now available.

If this season speaks to you, we hope our vision does too.

If you would like to learn more please schedule a call with our concierge team or reach out to Amy Kaemmer at amy@thesixtytwovail.com