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Vail's Free Halloween Trot Draws Crowds to Cobblestone Streets

Vail Recreation District hosts its free 34th annual Trick-or-Treat Trot Saturday, while Avon and Vail venues offer paid adult parties featuring cocktails, bingo, and costume contests.

Published Oct 31, 2026 · 1:26 AM3 min read
Vail's Free Halloween Trot Draws Crowds to Cobblestone Streets
Image source: Trick or treaters partake in the Vail Recreation District's Trick or Treat Trot in Vail.Weekend-VDN-103126-1

Aspen —The cobblestones of Vail Village are slick with October rain. Orange jack-o-lanterns glow in shop windows, casting long shadows across the pedestrian paths. It’s 2 p.m. on Saturday. The air smells like wet leaves and caramel corn.

This is the start of the 34th annual Trick-or-Treat Trot.

It’s a big weekend for Halloween on the Western Slope. But the biggest draw is right here in Vail. The Vail Recreation District is hosting the event. Kids can roam Vail and Lionshead Village from 2 to 5 p.m. on Halloween day. No registration is required. It’s free.

Make no mistake, this is the main event for families.

Participating merchants will display an orange jack-o-lantern in front of their establishments. That’s your guide. Follow the pumpkins. The villages are mostly pedestrian areas, but keep an eye out for town buses navigating the cobblestones. Watch your step.

If you want to get a head start, head to the Vail Public Library. Ms. Laurine is hosting a "Trick-or-Treat Trot Kick-Off Storytime" from 1 to 2 p.m. on Saturday. She’s serving up a special witch’s brew and reading spooky stories. It’s a good way to burn off energy before the candy hunt begins. Check vaillibrary.com for details.

Adults aren’t left out. Tavernetta Vail, located in the Four Seasons, is hosting "Tricks, Treats & Spritz" from 3 to 6 p.m. on Saturday. It’s an Italian-inspired Halloween party. You’ll find spritz drinks, passed bites, and food stations. There’s even an affogato stop. Kids can trick-or-treat at the Spritz Window. A DJ is spinning tunes.

There’s a costume contest. You walk the "runway" at 5 p.m. Tickets are $45 for kids and $95 for adults. It’s a step up from just handing out candy.

Over in Avon, Lookout Bar at the Westin Riverfront is hosting "Boos & Bingo" from 5 to 8 p.m. on Saturday. It’s bingo with a view. You get festive cocktails, bites, and prizes. There’s a costume contest. The winner takes home a $75 gift card to Lookout Bar. The winner is announced at 7:45 p.m.

Vail Brewing Company is also in on the action. They’re presenting a Halloween Bash at their EagleVail location. The details are still coming in, but expect beer and booze.

The short version: Vail is the hub. Avon is the alternative. If you’re in the valley, you’re going to be busy.

Read that again. The Trick-or-Treat Trot is free. The library storytime is free. The bars and restaurants charge you. Choose your budget.

The weather is turning. The sun sets early. By 6 p.m., the streets will be dark. If you’re out trick-or-treating, bring a flashlight. If you’re at a party, bring a coat.

Who’s winning the costume contests? We’ll see.

The candy is waiting.

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