Cristom Wine Dinner at Highlands Supper Club
2025-11-14 18:00 (America/New_York) | 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.

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

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, 2026-01-01 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.

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.

HF&W | Shot at Redemption at The Bascom
2025-11-16 11:00 - 14:00 | The Bascom, 323 Franklin Rd, Highlands, NC, 28741, United States
A Highlands Food & Wine Event
Due to capacity as a seated event, ticket priority is to VIP Weekender ticket holders. Additional tickets may come available.
5-time Grammy Award winning (and Lifetime Achievement award winner) Blind Boys of Alabama are back to join us on the mountain, 10 years later! They’re ready to bring us the gospel truth about why Sunday Brunch in Highlands is the best, and we’re sparing no expense. Rest and relax as we treat you to a seated-and-served multi-course brunch, complete with your favorite Bloody Mary bar, except we’ll do the work for you.

Seated brunch with plated and family-style delicacies
Sunday’s famous Ultimate Bloody Mary Bar, presented by Ketel One

Supper Social Club at Hotel Cashiers
2025-11-19 17:00 - 21:00 | Hotel Cashiers, 7 Slab Town Road, Cashiers, NC, 28717, United States
Join in every Wednesday for a special prix-fixe dinner menu!
Each week will offer a new concept created by Chef Kelly and will include a starter, entree, and desert as well as special pricing on wine selections curated by our very own sommelier, Gabriel.
Advance tickets offer a discount but walk ins are welcome based on availability. Book in advance and save! Reservations are recommended.

The Tailgate Cooperage | A Wine Club Event at Duck Hawk Provisions
2025-11-19 17:30 - 19:30 | Duck Hawk Provisions, 281 US 64, Cashiers, NC, 28717, United States
Become a member of the Duck Hawk Provisions Wine Club and unlock exclusive monthly pairing parties crafted just for you.
Join us for A Tailgate Cooperage. A Chili and Oregon Wines Party.

High Tea at Highlander Mountain House
2025-11-22 15:00 - 17:00, 2025-12-13 15:00 - 17:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Step into the season’s cozy magic with our traditional High Tea at Highlander Mountain House. Enjoy finger sandwiches, warm scones, and sweet treats paired with teas from Rosenthal’s and Highlands Spice & Tea (plus optional mulled wine).
Tickets are $80 + tax and available here.

Thanksgiving Dinner at The Ruffed Grouse
2025-11-27 11:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Gather with us this Thanksgiving at The Ruffed Grouse for a warm, festive celebration by Chef Adam Bresnahan!

Enjoy a four-course meal designed to bring everyone together, with thoughtfully paired wines available.

Tickets are $90 + tax and available here.

A Christmas Wine Bar Pop Up at Duck Hawk Provisions
2025-12-05 09:00 - 20:00, 2025-12-12 09:00 - 20:00, 2025-12-19 09:00 - 20:00, 2025-12-26 09:00 - 20:00 | Duck Hawk Provisions, 281 US 64, Cashiers, NC, 28717, United States
Fridays in December, we’re opening the cellar and keeping the Nest pouring until 8:00 p.m. Expect featured champagnes, cozy reds, and bottle discounts you won’t see every day. Holiday snacks are on: spiced pecans, bacon‑wrapped figs, and a few surprises.
Swing through when it suits you. Grab a glass, share a toast, stay a while. Good wine, good company, and a little December glow.

Holiday Hits: Festive Cheeses and Board Making Tips at One Wicker Cheese Co
2025-12-11 17:30 | One Wicker Cheese Co., 539 Main St, Highlands, NC, 28741, United States
Perfect for all cheese and wine enthusiasts!
Join us for the evening as we explore a selection of amazing cheeses paired with fun festive wines. We’ll talk through the basics of tasting, pairing and chat holiday board building tips!

"L'amour du Vin" | A Wine Club Event at Duck Hawk Provisions
2025-12-17 17:30 | Duck Hawk Provisions, 281 US 64, Cashiers, NC, 28717, United States
Become a member of the Duck Hawk Provisions Wine Club and unlock exclusive monthly pairing parties crafted just for you.
“L’amour du Vin” (love of wine event)
A lovely night featuring a French Menu and French Wines

Appalachian Holiday Tea at Highlands Supper Club
2025-12-19 14:00, 2025-12-20 14:00, 2025-12-21 14:00 | Highlands Supper Club, 130 Log Cabin Ln, Highlands, NC, 28741, United States
Celebrate the season with an afternoon of cheer and experience our new tradition at our Holiday Tea! Gather your friends to enjoy an Appalachian take on the Afternoon tea. We’ll provide the tea, and a tower of pimento cheese and smoked trout tea sandwiches, our favorite biscuits and jams, and sweets and treats, and of course have wine and great cocktails to add on.

Tour d’Italia Wine Dinner at High Country Wine & Provisions
2025-12-29 18:00 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
Join High Country Wine & Provisions for a grand tour of the wine regions of Italy, venturing from Piedmont to Sicily, where you will taste 10 exceptional wines, including selections from iconic estates such as Gaja, Ornellaia, and Giuseppe Gorelli! The evening’s tasting will be perfectly paired with a three-course dinner from Chef Johannes Klapdohr of The Library Kitchen.

NYE Wine Dinner at The Vineyard at High Holly
2025-12-31 18:30 | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join us for an extraordinary NYE Wine Dinner at The Vineyard at High Holly — where great wine, incredible food, and the perfect atmosphere come together for one magical night.
• Live music by the talented Tim Austin
• Exquisite wine pairings
• A beautifully curated dinner experience
• 6:30-10 P.M.
This is the celebration you’ve been waiting for. Raise a glass with us and welcome 2026 in style!
Limited seats — reserve your spot today!

Breeze Cable's Send-Off Performance at High Country Wine & Provisions
2026-01-03 17:00 - 19:00 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
From the High Country to Nashville!
Join us as we celebrate and bid farewell to our first hosted artist, Breeze Cable, before her big move. Fresh off releasing her Music City–recorded single, “Walk Away,” Breeze will perform her signature soulful set one last time at High Country Wine & Provisions.
Enjoy great wine, craft beer, and elevated BBQ as we toast the bright future of this incredible local artist. Stream her music on all platforms and join us for the final toast!

"Assagio di Lasagna" | A Wine Club Event at Duck Hawk Provisions
2026-01-14 17:00 | Duck Hawk Provisions, 281 US 64, Cashiers, NC, 28717, United States
Become a member of the Duck Hawk Provisions Wine Club and unlock exclusive monthly pairing parties crafted just for you.

Assagio di Lasagna (lasagna tasting)

Join us for a lovely night with a sampling of different lasagnas & Italian Wines

Outhouse Races Pre-& After-Party at Micas Mountain Kitchen
2026-02-07 11:00 - 21:00 | Micas Mountain Kitchen, 25 Logan Creek Trail, Sapphire, NC, 28774, United States
We’re celebrating your team and cheering squad at Micas for the Outhouse Races!
Fireplaces will be glowing, comfort fare and Hot Irish Coffees flowing, and our team will be in uniform to join you on the slopes and at the after-party.
Grab a commemorative tee and come experience The Firefly Bar — with live music, a full menu, and stunning views from our big deck.
Live music Friday & Saturday

Grand Reopening Celebration at Don Leon’s
2026-02-08 13:00 - 16:00 | Don Leon’s, 462 Dillard Rd, Highlands, NC, 28741, United States
Don Leon’s is celebrating its Grand Reopening on Sunday, January 25 from 1–4 pm, and the whole community is invited to join the fun.
Come meet the new owners, Ivanet and Juan Alvarado, wish Leon and Susan a happy retirement, and enjoy an afternoon of great food and live music.

Slow Season Supper Club | Chef Mari Vega at Flat Mountain Farm
2026-02-08 18:00 | Flat Mountain Farm, 1359 Flat Mountain Road, Highlands, 28741, United States
Join us at Flat Mountain Farm for a special communal supper hosted by acclaimed Atlanta chef Maricela “Mari” Vega, whose cooking celebrates through its use in seasonality, agriculture, and deep cultural lineage.
Inspired by her family’s Mexican roots in farming, Mari’s work centers heirloom corn, traditional techniques, and bold, grounded flavors. A James Beard–recognized chef, Mari is also a culinary educator and food stylist whose work has been widely featured in national and regional media.
For this evening, Mari will present a three-course (plus dessert), family-style dinner, served communally and designed for sharing. The menu will be vegetable-forward, but not vegetarian, highlighting the season’s harvest alongside thoughtfully sourced proteins, all enjoyed around the table in the setting of Flat Mountain Farm.
This dinner is an invitation to gather, slow down, and experience the intersection of land, culture, and craft through one of the Southeast’s most compelling culinary voices.

Super Bowl Sunday at High Country Wine & Provisions
2026-02-08 18:30 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
​Join us for the ultimate kickoff! Enjoy delicious snacks and exclusive features on wine, beer, and cider while you watch the game on our 86″ big screen!
