Calendar of Events Winter 2026

DECEMBER

Ice Skating in the Park

Ongoing

Each Thursday, Friday, Saturday, and Sunday, strap on your skates and take a whirl on the ice at Kelsey-Hutchinson Founders Park in Highlands. This annual event occurs from November through early March. Cost is $8 with or without skate rental.

DECEMBER

Winter Lights

Ongoing on Fridays

Local Fridays at Highlands Outpost. In search of fun for the whole family? Head on over to Highlands Outpost on Fridays, where locals can enjoy half-price snow tubing and rides on the Scaly Mountain Screamer. Bring your ID. Highlands Outpost is located at 7420 Dillard Rd, Scaly Mountain. highlandsoutpost.com

12 Days of Christmas

December 1

Running from December 1 through December 12, local holiday activities are organized by the Cashiers Area Chamber of Commerce. Times and activities vary across the schedule, so check the chamber website for specifics and ways to participate.

Holiday Market at The Bascom

Daily through December 27

The Holiday Market at The Bascom features a curated selection of handcrafted works by regional artists—unique gifts that support the creative economy—along with a variety of seasonal workshop offerings. Admission to the market is free, so come on out and support your local artisans. 323 Franklin Rd, Highlands.

Kids’ Nature Series: Wild Foraged Holiday Tea Making

December 2

Young participants join HCLT (Highlands – Cashiers Land Trust) to learn about wild foraging in the forest and how to blend herbs or plant materials into a holiday herbal tea mix. Held at Lewis Hall at The Village Green from 4 to 5 pm. 160 Frank Allen Road, Cashiers, NC.

Live Music from Woolybooger

December 5

Have a hankerin’ for some authentic Appalachian blues? Come on out between 5 and 7 pm to hear live music from Woolybooger. Plus, enjoy a beer or glass of wine at Western Carolina Brew and Wine, 454 Carolina Way, Highlands.

Holidays at the Historical Society

December 5 – 6

The Cashiers Historical Society presents a festive event at the historic Zachary-Tolbert House in Cashiers. Visitors will enjoy candlelit tours, holiday music, Victorian carols, and insights into Appalachian holiday traditions as they were celebrated in past eras. Come see the house decked out for the holidays, and enjoy seasonal treats and cheer. The event is held on Friday, December 5, from 4 to 9 pm, and on Saturday, December 6, from 6 to 9 pm. Tickets can be purchased at www.cashiershistory.org/holidays-2025. The Zachary-Tolbert House is located at 1940 NC-107, Cashiers.

Home for the Holidays

December 5, 6, 13, and 20

On these select dates, join the cast of Mountain Theatre Company to celebrate the most wonderful time of the year at their annual holiday spectacular. Fun for all ages, this festive seasonal music revue promises dazzling costumes and high-energy choreography, sure to inspire audiences with plenty of good, old-fashioned holiday cheer. Tickets are priced from $68 to $78. Local students under age 18 who are residents of Macon, Jackson, Transylvania, or Rabun Counties receive FREE Green Level tickets, reserved in advance. Experience the magic at Highlands Performing Arts Center, 507 Chestnut Street, Highlands. Mountaintheatre.com

51st Annual Cashiers Christmas Parade

December 6

Join us from 3 to 5 pm at the crossroads in Cashiers, as the town hosts our 51st Christmas Parade. Business leaders, community groups, and holiday entertainment will march or ride down Highways 107 and 64, offering a festive kickoff to the holiday season. Come out and see all your local favorites and (hopefully) grab some candy!

2025 Olde Mountain Christmas Parade

December 6

There’s nothing quite like a small-town parade! Gather all your family, friends, and neighbors and join the merry-making on Main Street in Highlands for this long-standing Christmas tradition. The parade begins at 10 am.

Paint and Sip: Winter Scene

December 6

Join a guided paint-along with Caryn Raming from 2 to 4:30 pm at The Bascom in Highlands. Wine and supplies are included. Participants will create a step-by-step winter painting as part of The Bascom’s Holiday Market workshop series. To register, call (828) 526-4949 or visit thebascom.org.

Wings for Thomas Pollinator Haven Design Workshop

December 11

A community design workshop focused on the Wings for Thomas Pollinator Haven runs from 2  to 4 pm at the Cashiers Area Chamber of Commerce. The project, as one of several community engagement events connected to the larger project, aims to create a certified pollinator waystation on the hillside west of the Chamber building.  Call (828) 743-5191 for more information. Cashiersareachamber.com

Opening of The Slopes at Sapphire Valley Resort

December 13

For all of you snow lovers and outdoor enthusiasts, the day you’ve been waiting for has arrived! From December 13 through March 1, the slopes are open at Sapphire Valley Resort. Come out and ski, snowboard, or zip down a frozen slope in a tube. It’s an adventure the whole family will love. Ski Sapphire Valley is located at 127 Sapphire Valley Rd, Sapphire.

Youth Origami: Holiday Stars and Trees

December 20

Join instructor Caryn Raming for this 10 am class at The Bascom, and learn how to make holiday stars and trees out of colorful paper. Everyone will take home bright and cheerful ornaments to share and hang up for the holidays! Call (828) 526-4949 to register your child for this class, or visit thebascom.org for more information.

Holiday Origami: Folded Stars and Trees

December 20

Adults learn the relaxing art of origami while creating stars and trees that bring a touch of peace and cheer to the season. It’s a calming, creative way to unwind—and you’ll leave with handmade ornaments to decorate your home or give as heartfelt gifts. Held at The Bascom at 2 pm.

To register, call (828) 526-4949 or visit thebascom.org.

JANUARY 2026

Ice Skating in the Park

Ongoing

Each Thursday, Friday, Saturday, and Sunday, strap on your skates and take a whirl on the ice at Kelsey-Hutchinson Founders Park in Highlands. This annual event occurs from November through early March. Cost is $8 with or without skate rental.

Bluegrass at The Ugly Dog Public House

Ongoing on Wednesdays

Bundle up and head on over to “the Dog” each Wednesday at 6 pm for some live bluegrass music. It’ll get your toes tappin’ and warm you up! The Ugly Dog Public House is located at 294 South 4th Street, Highlands.

Blues Night at Ruffed Grouse Tavern at Highlander Mountain House

Ongoing on Thursdays

From 6 to 8 pm at Highlander Mountain House, come enjoy “Blues Night” with Scott Low. This is a recurring live music event held on Thursday evenings, offering a relaxed setting for guests to enjoy blues music, food, and drinks. Highlander Mountain House is located at 270 Main Street, Highlands.

Carolina Concert Series at Trailborn Highlands

Ongoing on Thursdays

Beginning at 6 pm and running until

9 pm at Trailborn Highlands, this concert series features live music in an outdoor setting. It’s part of an ongoing weekly Thursday series that invites attendees to enjoy music, ambiance, and refreshments under the stars. Trailborn is located at 96 Log Cabin Lane, Highlands.

Paint (by Numbers) and Sip

Ongoing on Saturdays

Each Saturday from 12 to 3 pm, get in touch with your creative side in the lobby of Trailborn Highlands. The admission price of $50 includes two glasses of wine and all necessary materials to create the painting of your choice. Trailborn is located at 96 Log Cabin Lane, Highlands. Call 828-482-1578 for more information.

Cheese and Tipple

January 15

The perfect event for all cheese and wine enthusiasts! Explore a selection of amazing English cheeses and paired beverages. Learn the basics of tasting and pairing, sip wine, and chat about cheese. Price is $65 per ticket. Held at 5:30 pm at One Wicker Cheese Co.,

539 Main Street, Highlands. Call 828-482-4526 for more information.

Wings for Thomas Winter Seed Sowing

January 21

This winter seed sowing community event runs on Wednesday, January 21, 2026, from 5:30 to 7:30 pm at the Albert Carlton Cashiers Community Library, part of the Wings for Thomas Pollinator Haven series of community engagement events. Event details and partners are listed on the event page. Cashiersareachamber.com