4th Annual Harvest Lunch at Highlands Wine Shoppe
2025-11-14 12:00 - 16:00 (America/New_York) | Highlands Wine Shoppe, 269 Oak St, Highlands, 28741, United States
Highlands Wine Shoppe is bringing The Harvest BACK to Highlands!
Join us as we celebrate the magic + conviviality of the harvest season. Indulge in a delectable, harvest-inspired feast prepared by acclaimed Chef Ken Naron as you sip + savor your way through a selection of Old World + New World wines from around the world!

Live Music at The Vineyard at High Holly
2025-11-14 15:00 - 18:00 | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join us for live music at The Vineyard at High Holly!
Vineyard open hours 12-6 PM.

HF&W | Vines in the Pines at Highlands Biological Station
2025-11-14 16:00 - 17:30 | Highlands Biological Station, 265 N 6th St, Highlands, NC, 28741, United States
A Highlands Food & Wine Event
Hiking, but make it Highlands Food & Wine.
Partake in a guided stroll on the flat, manicured trails through the Botanical Gardens of the Highlands Biological Station with natural and sustainable wines tastings along the way.
The tour will culminate at the lakeside Teaching Pavilion for a sunset toast to our beautiful town.

HF&W | Her Voice, Her Vintage at Skyline Lodge
2025-11-14 16:30 - 18:00 | Oak Steakhouse at Skyline Lodge, 470 Skyliine Lodge Road, Highlands, NC, 28741, United States
A Highlands Food & Wine Event
Enjoy an early evening of conversation, songs, fine wine and hors d’œuvre pairings with American singer-songwriter and AMA nominated Emerging Artist of the year, Nikki Lane, nestled under Skyline Lodge’s outdoor pavilion.

Live Music with Mick Mayer at Western Carolina Brew and Wine
2025-11-14 17:00 | Western Carolina Brew and Wine, 454 Carolina Way, Highlands, NC, 28741, United States
Join us at Western Carolina Brew & Wine!
Come grab a pint and enjoy live music from Mick Mayer!

Wines of Germany Tasting at Western Carolina Brew & Wine
2025-11-14 17:00, 2025-11-15 17:00 | Western Carolina Brew and Wine, 454 Carolina Way, Highlands, NC, 28741, United States
You think Germany only has Riesling? Think Again!!
Join us Friday from 5:00pm – 7:00pm for a tasting of the lesser known varietal’s from Germany. Ian Scudder from Valckenberg International will guide you through a tasting of 5 wines from some of the most iconic vineyards in Germany. $25 per person.
Email to reserve: WesternCarolinaBrew@gmail.com

Live Music at Hummingbird Lounge
2025-11-14 17:30 - 22:00, 2025-11-15 17:30 - 22:00 | Old Edwards Inn and Spa, 445 Main Street, Highlands, NC, 28741, United States
Plush easy chairs, sofas, and antique bistro tables invite you to sit back and embrace the carefree ambiance surrounding you. Live entertainment every Friday and Saturday night with Cy Timmons.

Barrett Family Wine Dinner at On the Verandah
2025-11-14 18:00 | On the Verandah, 1536 Franklin Rd, Highlands, NC, 28741, United States
The Barrett Family Wine Dinner is a special evening of exceptional wines and seasonal cuisine, hosted by Remi Barrett. Guests will enjoy curated pours from the Barrett family portfolio alongside stories and insights shared by Remi herself.

Annual Farm Harvest Dinner at The Farm at Old Edwards
2025-11-14 18:00 | The Farm at Old Edwards, 336 Arnold Road, Highlands, NC, 28741, United States
Your senses will come alive with the sights, sounds, smells, and flavors of farm-fresh creations prepared live. Meet the farmers from Sunburst Trout Farm and Anson Mills and feast on their bounty. End the evening with the foot-stomping live music of Back Porch Orchestra.
It’s a fun, down-on-the-farm festival of the senses and a celebration of great Southern culinary traditions.

Cinder & Cellar Wine Dinner at Flat Mountain Farms
2025-11-14 18:00 | Flat Mountain Farm, 1359 Flat Mountain Road, Highlands, 28741, United States
A Fireside Pairing with Chef Santiago Guzzetti of Ilda and Sara Brewer of Boisset Collection
Step into an evening of refined indulgence as Chef Santiago Guzzetti of Ilda in Sylva presents a four-course French-inspired menu, each dish kissed by live fire and seasonal ingredients. With roots in Argentina and Italy and Michelin-level training, Guzzetti brings depth and elegance to every plate. The night begins with champagne and caviar under the open sky, then moves into a cozy barn setting for a seated dinner.

Cristom Wine Dinner at Highlands Supper Club
2025-11-14 18:00 | Highlands Supper Club, 130 Log Cabin Ln, Highlands, NC, 28741, United States
Enjoy a six-course evening of culinary artistry paired with exceptional wines from Cristom Vineyards.
Each dish—from oysters and goat cheese tart to duck breast and dark chocolate terrine—is matched with selections that showcase the elegance of Oregon’s Willamette Valley.
A celebration of flavor, craft, and connection.

Vino & Vibes | Live Music at High Country Wine and Provisions
2025-11-14 18:00 - 20:00 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
Joins us for Vino & Vibes, live music every Friday at High Country Wine & Provisions!

Vino & Vibes at High Country Wine & Provisions
2025-11-14 18:00 - 20:00 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
Join us for an evening of smooth music with The Highlands Horns.
We’ll be serving up your favorite wine, chilled craft beer, and delicious bites. Start your weekend off right!

Live Music at Happ's Place
2025-11-14 18:00 - 21:00, 2025-11-15 18:00 - 21:00 | Happs Place, 5914 NC-107, Glenville, NC, 28736, United States
Enjoy live music every Friday and Saturday at Happ’s Place in Glenville.

Morning Bird Walk at Highlands Nature Center
2025-11-15 08:00 | Highlands Nature Center, 930 Horse Cove Rd, Highlands, NC, 28741
Eyes to the skies! Birders of all skill levels are welcome to join us as we take an easy walk around the Highlands Biological Gardens to find our feathered friends.
Binoculars available to borrow. All ages welcome FREE | No registration required; Meet at 111 Lower Lake Rd
Weather dependent; Program funded by Highlands Biological Foundation

Mountain Findings Open
2025-11-15 10:00 - 13:00 | Mountain Findings, 432 Spruce Street, Highlands, NC, 28741, United States
A non-profit resale store featuring furniture, home accessories, lamps, tools, linens, pictures, tableware and more at reasonable prices!

The Church of the Good Shepherd Bazaar Barn
2025-11-15 10:00 - 14:00 | Bazaar Barn, 118 US Hwy 64 W, Cashiers, 28717, United States
The Bazaar Barn is an “upscale resale” shopping experience, offering gently used home furnishings.
Owned and operated by the Church of the Good Shepherd, the 10,000 square foot shopping center sells furniture, art and household items in styles ranging from antique to vintage to modern.
All of our items are donated, and all proceeds go directly back to the Cashiers community in the form of Outreach Grants.

Holiday Market at The Bascom
2025-11-15 10:00 - 17:00 | The Bascom, 323 Franklin Rd, Highlands, NC, 28741, United States
The Bascom’s Holiday Market is just around the corner!
Festive shopping in the Greehey Atrium – with unique handcrafted gifts by local and regional artists.⁠ Our line-up of seasonally themed workshops is already live, inviting all to create, learn, and celebrate the joy of making.
From gingerbread houses to ornament making, there’s something for everyone to enjoy.⁠

Football Weekend at High Country Wine & Provisions
2025-11-15 12:00 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
College Football Saturday and NFL Sunday is ON at High Country!
We’re going BIG with the games ALL DAY on our massive 90-inch screen—the best seat in town! Fuel your fandom with special features on wine, craft beer, and delicious game-day eats.
Gather your crew and settle in for great football and even better company. See you there!

HF&W | Main Event on Main Street Highlands
2025-11-15 12:00 - 15:30 | NC
A Highlands Food & Wine Event
The ONE not to miss: the Main Event! We take to the streets of Highlands, block-party style, with over 30 chefs and dozens of wines, specialty cocktails and mocktail brands, coffees, ciders and toddies galore. And don’t forget to dress to impress–The Style Watch is looking for those feeling their ‘fit and will get a little reward for their best put-together. We’re pining for the 90s and are proud to welcome HFW 2025 headliners and multi-Grammy winner The Wallflowers with opening support by Nikki Lane.

Access to the ultimate oyster roast
Small plates featuring local and regional chefs
Enjoy a selection of wines, craft beer, and spirits

Live Music on the Patio at The Ruffed Grouse Tavern
2025-11-15 13:00 - 15:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Join us for live music on the patio every Saturday at The Ruffed Grouse Tavern at the Highlander Mountain House!

Oakville Legacy & Meyer Family Cellars Seminar at Highlands Wine Shoppe
2025-11-15 13:30 - 15:30 | Highlands Wine Shoppe, 269 Oak St, Highlands, 28741, United States
In the 1970s, Justin Meyer + Ray Duncan founded Silver Oak, forever changing the landscape of American wine. That pioneering spirit lives on through Meyer Family Cellars, established in 1999 by Justin + his son, Matt.
We are honored to welcome Winemaker & Owner Matt Meyer for an unforgettable seminar celebrating his family’s enduring legacy.

Oyster Roast at Highlander Mountain House
2025-11-15 15:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Join us for a Lowcountry Oyster Roast featuring oysters from Pelican Oyster Company.

Your ticket includes all-you-can-shuck oysters, your first beer from Munkle Brewing, and live bluegrass on the porch from Flat Bridge String Band.

Tickets are $50 + tax and available here.

Live Music with The Highland Horns at Western Carolina Brew and Wine
2025-11-15 17:00 | Western Carolina Brew and Wine, 454 Carolina Way, Highlands, NC, 28741, United States
Join us at Western Carolina Brew & Wine!
Come grab a pint and enjoy live music from The Highland Horns!

HF&W | Rock & Roe at Hutchinson House
2025-11-15 17:30 - 18:30 | Hutchinson House, 594 Main St, Highlands, NC, 28741, United States
A Highlands Food & Wine Event
Pinky’s down please!
Here’s your exclusive invitation to taste and learn about some of the finest caviar and roe. And lest we forget the champs, courtesy of Veuve Clicquot.
Access to the home and grounds known as Hutchinson House, located just 1 block off of Main street Highlands.

Brochelle Wine Dinner at On the Verandah
2025-11-15 18:00 | On the Verandah, 1536 Franklin Rd, Highlands, NC, 28741, United States
Join us in welcoming Brochelle Vineyards for a multi-course wine dinner! Wines will be offered at a discounted rate for the night!

HFW | Barn Ramble at Flat Mountain Farm
2025-11-15 19:00 | NC
Gather with fellow festival-goers for a spirited evening at Flat Mountain Farm for the Barn Ramble: joining music, flavors, and community in one unforgettable place.
Enjoy local beer and wine, Blade and Bow cocktails, and Little Secret small bites while Nashville musician Sam Morrow fills the barn with a little bit of good ole southern rock.
