A Tale of Two Festivals

With fewer crowds, milder temperatures, and often lower prices, western North Carolina is an ideal hotspot for people planning weekend getaways in the months between peak season and the off-season. Referencing Highlands’ 150th anniversary celebration in 2025, Condé Nast Traveler honored the town as one of “The Best Places to Go in the US.”  For locals and tourists alike, the Highlands-Cashiers Plateau offers a unique blend of cosmopolitan experiences intertwined with the atmosphere of a relaxing wilderness retreat. While the primary tourist swell occurs during summer, Highlands Food & Wine and Bear Shadow Music Festival have served the area well, drawing thousands of visitors during the shoulder season.

Blending tradition with discovery, Highlands Food & Wine took place in the midst of autumn’s splendor, providing a 4-day celebration of world-class food, drink, and music.  The Hitting the High Notes tenth-anniversary festival on November 13-16, 2025, featured 60+ acclaimed chefs and 100+ beverage partners, with guests rocking to musical performances by The Wallflowers, Railroad Earth, Nikki Lane, and The Blind Boys of Alabama, among others.

In addition to the main festivities, numerous side events were offered throughout the weekend. Her Voice, Her Vintage featured Nikki Lane performing for an intimate crowd at the Skyline Lodge. Set outdoors against a blazing sunset, guests sampled wine and hors d’oeuvre pairings at what felt like a small, private party. The following evening, The Barn Ramble at Flat Mountain farm offered rocking tunes by Sam Morrow and craft cocktails by Blade & Bow. Guests–many of them locals–mingled, danced, and created a community mural in the festive rustic barn.

As celebrity chef Wolfgang Puck notes, “cooking is like painting or writing a song. Just as there are only so many notes or colors, there are only so many flavors - it's how you combine them that sets you apart.”  Highlands Food & Wine certainly provided attendees with a “set apart” experience that combined the finest of ingredients:  delectable bites, sensational sips, and renowned musicians.

Sadly, in the face of logistical challenges posed by widespread construction projects in downtown Highlands, organizers recently made the difficult decision to sunset Highlands Food & Wine. While local and visiting foodies alike will miss the annual festivities, opportunities to create new memories will surely emerge as the town pivots toward the future.

Born from the popularity of Highlands Food & Wine, Bear Shadow made its debut in April 2021 and soon became a phenomenon all to itself.  After a year-long hiatus due to a change of venue, fans of Bear Shadow can now celebrate its return to Highlands, NC, from May 29th-31st, 2026. The 2026 Bear Shadow music festival lineup features headliners Trombone Shorty (Saturday) and Charley Crockett (Sunday). Mavis Staples, Margo Price, Marc Broussard, Kashus Culpepper, Pony Bradshaw, and J & The Causeways.

“We are bringing the heat with this lineup!” says Casey Reid, festival director and partner at Eleven Events. “After taking a year off, we knew our fans would be ready to rock again. The artists on our 2026 lineup are Grammy award winners, nominees, and performers – proof positive that Bear Shadow is a must for the industry’s top talent ... and a must-see for our fans.”

Local business partners Cristina Vives and Faye Wurm enthusiastically support Bear Shadow’s vision of music, mind, body, and nature. Cristina and her fiancé have been loyal attendees since 2022, noting that they often attend with a mix of local friends, as well as out-of-town guests. “We especially love that you can bring blankets and lawn chairs and really settle in and take your shoes off! It feels like you’re hanging out in your own backyard with friends — just with world-class musical talent as the soundtrack. The atmosphere is welcoming, social, and thoughtfully curated. It’s a blend of community, music, and mountain lifestyle.”  Fellow music lover Faye shares that she has “knocked off quite a few of [her] ‘bucket list’ performances that would be hard to see anywhere else.” She especially appreciates the “intimate feel of the festival... something that makes this a craveable experience, adding to the nostalgia that [she is] looking forward to experiencing again.”

Bear Shadow, produced by Highlands Festivals, Inc. and Eleven Events, is named in honor of the bear-shaped shadow that appears behind the region’s Whiteside Mountain in the fall and spring. “This festival brings new energy to Highlands each spring — from supporting local businesses to showcasing the beauty of our town and region,” said Jack Austin, president of Highlands Festivals, Inc.

Known for its charitable impact across the region, Highlands Festivals Inc. has contributed over $250,000 to numerous charities and non-profit organizations over the past 10 years. This year, a portion of festival proceeds will benefit Stage4Hope, a public charity connecting advanced-stage cancer patients to lifesaving treatment, travel support,   emotional-wellness retreats, and lung cancer research.

Equally exciting is the festival’s new Base Camp location, “After taking time to find the right fit, we’re thrilled to announce Ferngrove as the new home for Bear Shadow,” said Jack Austin, Board President of Highlands Festivals, Inc. “This venue captures the natural beauty and sense of community that have always been at the heart of the Festival.”

Stacey Carter, Founder of Ferngrove and the nonprofit Stage4Hope, welcomes the festival wholeheartedly, “It’s a beautiful way to bring people together through music and to highlight Stage4Hope. Our new cancer wellness center at Ferngrove will extend that mission here in Highlands—a place where patients and families can breathe, find hope, and rediscover purpose again."

Brew Davis of the Asheville-based band Nick & Brew affirms that "Western North Carolina has long been a hotbed for bluegrass and mountain music, so it's no surprise we have some of the best festivals in the world. Mountain Song in Brevard, Scruggsfest outside of Shelby, Merlefest in Wilkesboro. Bear Shadow is definitely in that top-tier category. It leans a bit more Americana, which sets it apart and has a killer lineup year in and year out. Charley Crockett is one of the hottest Americana artists out there. Mavis Staples is an icon. The Stringdusters, Margo Price, and Kashus Culpepper, these are some heavy hitters. It's kind of crazy that a small place like Highlands is bringing these world-class artists in when they're used to playing much bigger festivals and arenas. It's just very cool to see and a credit to the community."

Both festivals are/were organized by Highlands Festivals, Inc., a 501(c)(3) non-profit organization “dedicated to promoting the Highlands-Cashiers Plateau as an inspiring place to live and visit.” A portion of ticket sales contributed over $250,000 to numerous charitable and non-profit organizations, such as The Bascom, Scaly Mountain Fire & Rescue, Highlands-Cashiers Land Trust, Highlands Biological Station, Highlands Food Pantry, Friends of Kelsey-Hutchinson Founders Park, and Hurricane Helene recovery efforts. In addition, the events funded a scholarship endowment to the Culinary Institute of America and generated tens of millions of dollars in economic impact for the Plateau. As our beloved mountains set the scene for events large and small, let us continue the spirit of giving back to the land that provides such bountiful joy.

Visit bearshadownc.com to purchase tickets and to plan your spring-time adventure with bonus options that include Livestream: fly fishing excursions and Summit & Sound: guided hikes, complete with an up-close-and-very-personal music experience overlooking high vista views.