HF&W | Main Event on Main Street Highlands
2025-11-15 12:00 - 15:30 (America/New_York) | 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, 2025-11-26 17:00 - 21:00, 2025-12-03 17:00 - 21:00, 2025-12-10 17:00 - 21:00, 2025-12-17 17:00 - 21:00, 2025-12-24 17:00 - 21:00, 2025-12-31 17:00 - 21:00, 2026-01-07 17:00 - 21:00 and 4 more dates | 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

Live Music at Highlands Smokehouse
2026-02-01 13:00 - 15:00 | Highlands Smokehouse
Enjoy live music – and delicious eats – weekly on Wednesdays and Sundays at Highlands Smokehouse.
