Trailborn Highlands
Fall in Highlands
Fall brings out the best of Highlands: cool mornings, golden afternoons, bright foliage, and waterfall trails that feel made for the season. Spend the day chasing cascades, driving mountain roads, browsing galleries, or catching a local festival, then return to Trailborn for dinner at Highlands Supper Club. It’s a mountain escape with just the right mix of adventure, color, and cozy.
Fall Experiences
Make the most of the season with experiences that lean into the cooler weather, mountain setting, and slower pace of fall. Start outside, come back warm, and leave room for dinner.
Guided Outdoor Excursions
Book a guided day outside, from fly fishing to rock climbing. Fall brings cooler air, clearer views, and just enough adventure before supper back at the cabin.
Paint (By Numbers) and Sip
Settle in for a relaxed afternoon of painting and sipping at Trailborn Highlands. No art expertise required—just pick your palette and let the mountain setting do the rest. Saturdays at noon, from $50.
Back Patio & Firepit Lounging
Book the Nordic Spa or just bring a layer and settle in out back. The firepit is made for cool mountain nights, slow conversations, and one last drink under the trees.
Local Fall Happenings 2026
Carolina Concert Series
Thursdays, August 27 - October 29
Settle into the Trailborn Highlands backyard for complimentary live music and drinks every Thursday evening, 6–9 p.m. It’s an easy, on-property start to a fall night in the mountains.
Thursdays, August 27 - October 29
Settle into the Trailborn Highlands backyard for complimentary live music and drinks every Thursday evening, 6–9 p.m. It’s an easy, on-property start to a fall night in the mountains.
Dazzling Dahlia Festival
September 10-12
The Bascom’s six-acre campus fills with dahlias, floral design, pottery, and art for its 16th annual festival. Admission and scheduled programs are free.
September 10-12
The Bascom’s six-acre campus fills with dahlias, floral design, pottery, and art for its 16th annual festival. Admission and scheduled programs are free.
Bel Canto Recital
September 13
Internationally recognized singers perform opera arias and Broadway favorites at Highlands Performing Arts Center, followed by an optional gala dinner with the artists.
September 13
Internationally recognized singers perform opera arias and Broadway favorites at Highlands Performing Arts Center, followed by an optional gala dinner with the artists.
Highlands-Cashiers Film Festival
September 17-20
Spend four days discovering independent films, filmmaker conversations, and special events at Highlands Performing Arts Center.
September 17-20
Spend four days discovering independent films, filmmaker conversations, and special events at Highlands Performing Arts Center.
Highlands Porchfest
September 20
Downtown porches and patios become open-air stages during this free community music festival, 1–6 p.m. Wander between performances while exploring Main Street.
September 20
Downtown porches and patios become open-air stages during this free community music festival, 1–6 p.m. Wander between performances while exploring Main Street.
Highlands Heritage Jamboree
September 26
Celebrate the music and traditions of the mountains with live performances, mountain dance, local history, barbecue, and moonshine at Founders Park. Admission is free.
September 26
Celebrate the music and traditions of the mountains with live performances, mountain dance, local history, barbecue, and moonshine at Founders Park. Admission is free.
Walk in the Park
October 3-4
Meet actors portraying some of Highlands’ most memorable historical figures during a guided cemetery walk on Saturday or a seated performance on Sunday. Reservations are required.
October 3-4
Meet actors portraying some of Highlands’ most memorable historical figures during a guided cemetery walk on Saturday or a seated performance on Sunday. Reservations are required.
Cashiers Valley Leaf Festival
October 9-11
Take a scenic drive to Cashiers for a free, rain-or-shine celebration featuring 100 artisans, local food and drinks, live mountain music, and family activities at The Village Green.
October 9-11
Take a scenic drive to Cashiers for a free, rain-or-shine celebration featuring 100 artisans, local food and drinks, live mountain music, and family activities at The Village Green.
Full Event Calendar
All Season
From gallery workshops to concerts, lectures, and performances, Highlands keeps its cultural calendar full through the season. Check what’s on before you arrive.
All Season
From gallery workshops to concerts, lectures, and performances, Highlands keeps its cultural calendar full through the season. Check what’s on before you arrive.
Top Things to Do During Fall
In 48 Hours
The Fall Weekend Edit
Start early with Dry Falls, Glen Falls, or a scenic drive along Highway 64. The morning light is softer, the trails are quieter, and the cooler air makes every stop feel easy.
Ride a complimentary cruiser bike into town to browse Main Street, visit The Bascom, or take a short hike to an overlook. Fall is best when the day has room to wander.
Return to Trailborn for Après Hour, then make your way to Highlands Supper Club for cocktails and contemporary Southern comfort food in our historic log cabin.
End the day outside. Bring a layer, grab a drink, and settle in by the firepit while the mountain air cools around you.
Fall, Well Spent
Hikes & Waterfall Weather
Highlands sits high in the Blue Ridge, which means crisp air, layered views, and a leaf season worth lingering over. Pack a sweater, leave room in the day, and take the scenic route.
Supper Club Season
Fall evenings are made for smoky cocktails, contemporary Southern comfort food, and a fireside table in our historic log cabin, tucked into the trees. End the day at Highlands Supper Club and let the mountain night slow down.
Offers & Packages
From dining credits to seasonal perks, our offers make it easy to turn a Fall weekend into something more. Add a Supper Club dinner, plan an experience, and let the mountain do the rest.
