From a sunset lichen walk on November 13 to skating into 2027 on New Year’s Eve, here is what’s on the calendar in Highlands, Cashiers and Sapphire, with a link to tickets or details for every event.
The holidays on the Highlands-Cashiers Plateau run on tradition: Santa arriving by fire truck in Kelsey-Hutchinson Founders Park, candlelit tours of the 1850 Zachary-Tolbert House, and two Christmas parades on the same Saturday. This year the season opens with the first Highlands Culinary Week.
Several of these events have limited seats or registration caps, so book early, and check the organizer’s page before you go in case details change.
Jump to: Culinary Week weekend · Thanksgiving week · December
Culinary Week Weekend: November 12 to 15
Highlands Culinary Week debuts November 12 to 15 with chef dinners, tastings and live music around town. Our picks from the schedule are below, along with two free events from the same weekend. See the full Culinary Week schedule.
Whiskey & Flannel Night at The Stubborn Bull
Thursday, November 12 · 5:30 to 8:30pm · The Stubborn Bull, Highlands
The Stubborn Bull closes its live music season with a Still Austin whiskey cocktail menu, a set from singer-songwriter Rara Kay and DJ Kyle Rhodes taking requests. Cocktail proceeds help local families, and the night doubles as a food drive for Hampton Preschool & Early Learning. Reservations are through Resy.
Sunset Lichen Walk at Sunset Rock
Friday, November 13 · 4 to 7pm · Sunset Rock trailhead, Highlands
Highlands-Cashiers Land Trust naturalist Stephanie Contreras leads a half-mile hike up to Sunset Rock, stopping to study the lichens along the trail and on the granite outcrop, then stays for the sunset before the walk back down. Free, with registration required. Meet at the trailhead at 945 Horse Cove Road, where parking is limited.
High Tea at Highlander Mountain House
Saturday, November 14 · 3pm · Highlander Mountain House, Highlands
Finger sandwiches, warm scones with jam and sweets, served fireside with selected teas, in partnership with neighbors Rosenthal’s and Highlands Spice & Tea. $60 per person includes three teas and food; a 20% service gratuity is added.
Sip & Stroll at Skyline Lodge
Saturday, November 14 · 4 to 7pm · Skyline Lodge, Highlands
Wander the Skyline Lodge grounds, glass in hand, while Zorki plays and the fires crackle. Tastings come from Davis Family Vineyards, Western Carolina Brewing, Stubborn Buddha and The Stubborn Bull, Highlands Smokehouse and Indigenous Chocolate, with seasonal bites from Markie and Ashley. $125 per person.
Am Meer Quartet Free Concert
Saturday, November 14 · 5pm · Episcopal Church of the Incarnation, Highlands
The Highlands-Cashiers Chamber Music Festival brings the Am Meer Quartet to the Church of the Incarnation on Main Street for a free fall residency concert, with a wine reception immediately after. Sponsored by Cullasaja Women’s Outreach. Questions: (828) 526-9060.
A Toast to Tradition: Domaine Parent Wine Dinner
Saturday, November 14 · 6pm · On the Verandah, Highlands
Burgundy winemaker Anne Parent of Domaine Parent brings her farewell tour to On the Verandah for a dinner with Chef Andrew Figel. $250 per person; reserve through On the Verandah at (828) 526-2338.
Holiday Kickoff and Thanksgiving Week: November 19 to 28
Ice Skating in Highlands: The Rink Opens November 19
Opens Thursday, November 19 · Kelsey-Hutchinson Founders Park, Highlands
The Highlands ice rink is open through February 28: Thursdays 3:30 to 8pm, Fridays 3:30 to 10pm, Saturdays 1 to 10pm and Sundays 1 to 5pm, with extra afternoon hours during Thanksgiving and Christmas weeks. It’s closed Thanksgiving Day and Christmas Day. Admission is $8 with or without skates, rentals run from youth size 8 to adult 14, and coffee and hot chocolate are on hand. No reservations needed.
Salon Series at Highlander Mountain House: S.G. Goodman and Tift Merritt
Thursdays, November 19 and December 17 · 8:30 to 11pm · Ruffed Grouse Tavern, Highlands
Highlander Mountain House’s Salon Series brings songwriters into the Ruffed Grouse Tavern. S.G. Goodman, who has opened for Tyler Childers and Jason Isbell, plays November 19, and Grammy-nominated singer-songwriter Tift Merritt plays December 17. Seating is first come, first served, and dinner reservations (5:30 to 8pm) are separate from the show ticket.
S.G. Goodman Tickets · Tift Merritt Tickets
Forest Bathing Hike on Whiteside Mountain
Friday, November 20 · 1 to 4:30pm · Whiteside Mountain Trailhead, Highlands
Dr. Mark Ellison leads a Highlands-Cashiers Land Trust forest bathing hike on Whiteside Mountain: 2 miles round trip with 525 feet of elevation gain, taken slowly with frequent stops. Free with registration and limited to 15 people. Parking at the Deville Drive trailhead is $3 per car.
The Land Trust’s calendar runs through mid-December, with spoon whittling, lino-cut block printing, a naturalist walk at Brushy Face Preserve, a forest bathing hike to High Falls and wildcraft wreath making.
Mark O’Connor’s An Appalachian Christmas in Highlands
Saturday, November 21 · 7:30pm · Highlands Performing Arts Center
Three-time Grammy winner Mark O’Connor returns to the Main Stage with An Appalachian Christmas, his holiday program featuring Maggie O’Connor. Reserved seating; box office (828) 526-9047.
Gobble on the Green: Cashiers Thanksgiving 5K
Thanksgiving Day, Thursday, November 26 · 9am · The Village Green, Cashiers
Start Thanksgiving with The Village Green’s 5K run/walk, on a new 3.2-mile course this year. Registration is $40 through RunSignup and supports The Village Green, and kids can run the free Junior Warrior obstacle course at the playground from 9:30 to 10:30am. Packet pickup is Wednesday, November 25, 3 to 6pm at Lewis Hall. Rain or shine.
Lights on the Green: Cashiers Tree Lighting
Friday, November 27 · 5 to 7pm · The Village Green, Cashiers
The trees on The Village Green light up around 5:45pm, with treats for everyone and a s’mores village for kids. Free.
Cashiers Festival of Trees 2026
Friday and Saturday, November 27 and 28 · 10am to 5pm · Summit Center, Cashiers
Decorated trees and wreaths fill the Summit Center for a festival benefiting the Summit Charter School Foundation and local nonprofits. When a nonprofit decorates a tree or wreath, 80% of its sale goes back to that nonprofit. $5 for adults, good for both days; free for ages 18 and younger.
Small Business Saturday and Light Up the Park & Main
Saturday, November 28 · 11am to 4pm and 6 to 8pm · Downtown Highlands
Shop local in downtown Highlands from 11am to 4pm, with a cookie crawl, music in Town Square, face painting at The Bascom, story time at Hudson Library and ice carving in Town Square at 3pm. At 6pm, Light Up the Park & Main brings carols, treats, a reading by the Mayor and Santa on a fire truck to Kelsey-Hutchinson Founders Park.
December Traditions
The Bascom Holiday Market
Through December 26 · Tuesday to Saturday, 10am to 5pm · The Bascom, Highlands
The Bascom’s Holiday Market gathers handcrafted gifts from local and regional artists: ceramics from Bascom studio members, plus textiles, glass, woodworking, jewelry, books and cards. Free. Black Friday weekend (November 27 and 28) adds hot chocolate, cookies and letters to Santa, and a December 5 reception after the Highlands parade, from 2 to 4pm, brings a trunk show, hot chocolate and cheese straws.
Holidays at the Historical Society, Cashiers
Thursday and Friday, December 3 and 4 · 4 to 8:30pm · Zachary-Tolbert House, Cashiers
Walk through the 1850 Zachary-Tolbert House by candlelight while the caroling ensemble Thruppence sings 19th-century carols in the parlor, make a wreath with the Highlands-Cashiers Land Trust in Crooked Corners Cabin, and warm up with hot cider at the Dowden Pavilion. Tickets are timed: $55 for adults, $20 for ages 5 to 17 and free under 5. Guided house tours at 5:20 and 7:40pm must be reserved when you buy.
Highlands and Cashiers Christmas Parades 2026
Saturday, December 5 · 10am in Highlands · 3pm in Cashiers
Highlands: The parade starts at 10am along Main Street, a free tradition, and Santa visits Kelsey-Hutchinson Founders Park afterward until 3pm.
Cashiers: The 52nd annual parade, a tradition since 1974, starts at 3pm at Frank Allen Road and US 64 West, rolls through the Cashiers Crossroads, turns south on Highway 107 and ends at Cashiers School Road.
Highlands Parade Details · Cashiers Parade Details
HCFF Prelude: Papertown
Sunday, December 6 · 4pm · Highlands Performing Arts Center
The Highlands-Cashiers Film Festival’s 2026 Best Documentary winner returns for a screening in the Martin Lipscomb Theatre, followed by a talkback Q&A. Filmed in real time, Papertown follows Canton, North Carolina, through the months after its paper mill announced it would close. Tickets are $20 plus fees, and Film Festival Society members, donors and sponsors can reserve an included seat through the box office at (828) 526-9047.
Sapphire Valley Resort Holiday Festival
Saturday and Sunday, December 12 and 13 · 10am to 4pm · Sapphire Valley Community Center, Sapphire
Sapphire Valley Resort’s second annual winter arts and crafts festival fills the Community Center, inside and out, with local artisans, folk art, live music and food, and the Slopeside Tavern is open for food and drinks.
New Year’s Eve Skate in Highlands
Thursday, December 31 · 1pm to 1am · Kelsey-Hutchinson Founders Park, Highlands
The Highlands ice rink stays open until 1am on New Year’s Eve, so you can skate into 2027. Admission is $8 with or without skates.
Thinking About a Home in Highlands or Cashiers?
If these weekends have you picturing a place of your own, start with our guides to Highlands, Cashiers and Sapphire, or call our team at (828) 526-1717. You’ll find us on Main Street in Highlands and on Burns Street in Cashiers.
