The Bear Shadow Festival supports local organizations - Carolina Country

Music in the Mountains

Support local organizations at the Bear Shadow Festival

By Renee C. Gannon

Music in the Mountains

Bear Shadow Festival

Music, Mountains and Revelry. That’s the tagline for an annual gathering of about 2,000 music enthusiasts at the Winfield Farm in Scaly Mountain, all ready to listen to national artists with the Blue Ridge Mountains as the backdrop. This year’s festival on May 11–12, 2024, will feature eight performers, including Grace Bowers, American Aquarium, North Mississippi Allstars and Grammy-nominated Black Pumas.

While attending the 2023 Bear Shadow Festival in the southwestern mountain town of Highlands, situated on the Highlands-Cashiers Plateau, I noted that the gathering could also be dubbed “Music, Nature and Conservancy”—the festival raises funds for the local Highlands-Cashiers Land Trust Conservancy, which purchases, builds and maintains land for all to enjoy the area’s natural environs.

According to Hillary Wilkes who, along with her husband, Christopher, owns the local Highland Hiker outfitter store, the festival began as a part of the annual fall Highlands Food & Wine Festival, but town planners decided to split the music scene into a “shoulder season” event and tie it to land conservation awareness, giving a portion of the festival’s profits to the local land trust organization.

Casey Reid, Bear Shadow Festival director, adds that “as a 501c3, it’s important that the festival gives back to the community.”

Since 2001, approximately $50,000 has been given to the trust and other local non-profits. This year, Scaly Mountain Volunteer Fire & Rescue will also benefit.

Music festival highlights

At last year’s festival, I recognized many, but not all, of the performers. The final night’s headliner, Jason Isbell, did not disappoint. I walked away a bigger fan of other known artists Spoon and Lissie, and a new fan of the unknown such as Amythyst Kiah, Myron Elkins and Neal Francis.

Amythyst Kiah

Amythyst Kiah. Photo courtesy of Bear Shadow Festival

The festival offers an array of food and beverage vendors, as well as local businesses and organizations. And a free shuttle service from downtown Highlands to the festival grounds is a nice touch for visitors.

Two changes from past festivals: to accommodate attendees’ travel time, the festival moves to a two-day event instead of three; meaning the music and revelry start earlier on Saturday, last through the evening and continue all day on Sunday. The fun also moves to mid-May, instead of April.

Adds Casey: “We really want all to experience the beauty the area has to offer in the warmer month of May. Bear Shadow is a family-friendly festival, and this year, all children 12 and under have free admission.”

Environs worth visiting

Whether you are attending the festival or just visiting the Highlands area, plenty of outdoor activities beckon. I hiked within the Brushy Mountain Preserve, enjoyed an overlook view of Highlands from Sunset Rock in Ravenel Park, and trekked to Ranger Falls.

Highland Botanical Garden

Renee C. Gannon

Other activitivies could include a low-key walk through Highlands Botanical Garden, an ideal way to work off your breakfast from one of the many local restaurants. Also highly recommended is a visit to The Bascom, a center for visual arts that offers visitors six acres of outdoor space, local artists’ exhibits, a sculpture trail and other scenic views. 

To learn more about where to eat, what to do and where to stay, visit

About the Author

Renee C. Gannon is the senior associate editor of Carolina Country.

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