Annual Events in Westcliffe, CO

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Your Guidebook

Annual events in Westcliffe & Custer County

A social calendar packed with fun & tradition

Westcliffe may be a small town, but it’s far from sleepy. The community gathers together often to celebrate holidays and our time-honored traditions.

Enjoy everything from an annual bluegrass festival that attracts thousands of visitors and world-class talent to our old-fashioned, small-town parades held for just about every holiday. (To be a part of the parade, you only need to be able to walk. Or drive.)

Explore some of the special events that help make Westcliffe, Westcliffe.


high mountain hay fever festival

This 4-day annual festival is one of America’s premier bluegrass events, attracting nationally-renowned talent and thousands of bluegrass fans from around the country. Yet, at the same time, it lacks the congestion and overwhelming crowds found in most festivals.

Held in the park with panoramic views of the Sangre de Cristo mountains, it makes for one of the best concert venues you could imagine. Don’t miss this favorite event!

For the latest dates and tickets, visit

rock n'soul jam

A day of music featuring Classic Rock from the 50s, 60s, and 70s, plus Motown and Soul. Held by KLZR 91.7FM, the Wet Mountain Valley’s hometown radio station, you’ll love the excellent regional bands and impossible-to-top atmosphere.

high peaks music festival

The High Peaks Music Festival has been a Custer County tradition for over 10 years. This one-day festival, held every September, showcases the Valley’s amazing musical talent. Mark you calendars for great music, food, and drinks.

summer in the park concert series

Enjoy a free concert in the park on Sunday afternoons throughout the summer. The lineup features a diverse array of musical talent, including folk, Americana, and bluegrass. With the Sangre De Cristo mountains as the backdrop, it’s hard to beat a summer afternoon spent here.


shakespeare in the sangres

Imagine an evening of Shakespeare in an outdoor amphitheater, watching the sun set over the Sangre de Cristo Mountains as you enjoy a family picnic on the lawn. The Westcliffe Center for Performing Arts puts on two plays with performances throughout the summer.


Art for the sangres

Art for the Sangres is the annual benefit for the San Isabel Land Protection Trust, a land trust that has protected nearly 41,000 acres of working ranches, agricultural and forest lands, water resource, and wildlife habitat in Colorado. Attendees can enjoy a gala and reception with fine food and drink, plus a silent auction.

arts hullabaloo

The Sangres Art Guild’s annual Arts Hullabaloo features three days of family fun, with a focus on showcasing visual arts, performing arts, culinary arts, fiber arts, and literary arts, to name a few. This free, public event features exhibits around town, with street art, face-painting, chalk art, tie-dying and more. 

Check the Sangres Art Guild website to see what they have planned for the next year’s event.

Fourth of July

The Fourth of July is a BIG deal in Custer County. It’s truly a multi-day extravaganza with events planned by various groups and vendors throughout town. Kick it off with the annual craft show and flea market. Then enjoy a pancake breakfast and old-fashioned parade. And whatever you do, don’t miss the incredible fireworks display over DeWeese Reservoir!

Memorial Day

Custer County always kicks off the summer season with a parade on the Saturday of Memorial Day Weekend. Don’t miss the small-town fun as the community gathers on Main Street for this beloved tradition.

Hardscrabble Mountain Trail Run

This popular event held at Bear Basin Ranch features a 10K run, 5K walk and run, and a post-race party with live music and a gourmet lunch. It’s one of the biggest annual sports events in Custer County, and the trail runs have become a fixture on the calendars of many runners from across the region.

Rodeo & Fairs

westcliffe stampede rodeo

A mainstay on the Colorado rodeo circuit since 1946, the Westcliffe Stampede Rodeo pays homage to our town’s rich ranching history. Held on the third weekend of July, it’s an action-packed weekend of fun with exceptional competition. And, of course, Westcliffe shuts down Main Street for another small-town parade in celebration.

custer county fair

Another long-standing annual tradition, 4H and Future Farmers of America have been holding the Custer County Fair since 1947. The community is welcome to attend and compete in classes like needlework, quilting, photography, fine art, horticulture, cooking, archery, and much more.

High Altitude Horsepower Car Show

Come see antique, vintage, classic, rat road, hot road, and muscle cars. This popular annual event draws car enthusiasts from across the state.

Explore more

Custer County event calendar

Get the details on all upcoming events with this up-to-date online event calendar.

Custer County Visitor's Guide

Download a free visitor’s guide and stay informed about everything there is to see and do in Custer County.