Star-Spangled Celebration at The Vineyard at High Holly
2025-07-04 12:00 - 18:00, 2025-07-06 12:00 - 18:00 (America/New_York) | The Vineyard at High Holly, 37 High Holly Rd, Scaly Mountain, NC, 28775, United States
Join The Vineyard at High Holly for wine, live music & food from July 2–6, 12-6pm.
Live Music Thurs, Fri., and Sun 2-5pm.
(closed Saturday)

Pig Pickin On The Hill at Highlander Mountain House & The Ruffed Grouse Tavern
2025-07-04 17:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Celebrate July 4th with an outdoor pig roast. We will have live music, sparklers & s’mores. Catch the fireworks from our patio.

Under the Stars, on the Rocks | Chef Trey Smith at Skyline Lodge
2025-07-08 18:00 | Oak Steakhouse at Skyline Lodge, 470 Skyliine Lodge Road, Highlands, NC, 28741, United States
Enjoy a one-of-a-kind dining experience with our premier guest chef dinner series, “Under the Stars, On the Rocks”. Hosted at Skyline Lodge against the stunning Blue Ridge Mountains, this event offers an al fresco steakhouse dining experience. Featuring collaborations with renowned chefs from around the country and Oak Steakhouse’s culinary team, each four-course meal will be family-style and is unique and personalized to the guest chef.
For $175 per person, including beverage pairings, plus tax and gratuity.
Chef Trey Smith is co-owner and chef at Saint-Germain, an intimate tasting-menu restaurant in New Orleans’ Bywater neighborhood. He collaborates with Chef Blake Aguillard and General Manager Drew DeLaughter to offer a dynamic culinary experience that blends French influences with Southern roots. Before establishing Saint-Germain, Trey strengthened his culinary skills at Restaurant August under Chef Michael Gulotta. He later joined Mopho as the opening chef de cuisine and contributed to the launch of Maypop. His dedication to innovative cuisine has earned him multiple nominations for “Best Chef: South” from the James Beard Foundation.

Supper Social Club at Hotel Cashiers
2025-07-09 17:00 - 21:00, 2025-07-16 17:00 - 21:00, 2025-07-23 17:00 - 21:00, 2025-07-30 17:00 - 21:00, 2025-08-06 17:00 - 21:00, 2025-08-13 17:00 - 21:00, 2025-08-20 17:00 - 21:00, 2025-08-27 17:00 - 21:00 and 5 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.

Pride Mountain Vineyards 'Atelier' Tasting featuring Special Guest Corey Crowe
2025-07-31 17:00 | Highlands Wine Shoppe, 269 Oak St, Highlands, 28741, United States
Join Highlands Wine Shoppe for a very special tasting featuring Special Guest Corey Crowe of Pride Mountain Vineyards—one of Napa Valley’s most iconic + acclaimed wineries!
Perched high atop the Mayacamas Mountains at elevations reaching 2,100 feet, Pride Mountain Vineyards straddles the Napa and Sonoma county line and is renowned for producing powerful yet elegant wines that reflect their dramatic terroir.

Vino and Vibes with at High Country Wine and Provisions
2025-08-03 17:00 - 19:00 | High Country Wine & Provisions, 621 Franklin Rd, Highlands, NC, 28741, United States
Will and Lindsey are a dynamic musical duo known for their heartfelt performances and harmonious blend of sounds. Based in Panama City, Florida, they share a deep passion for music that has brought them together both personally and creatively. With Will’s soulful energetic voice and Lindsey’s enchanting vocals and piano playing, they create a captivating experience for their audience.
Don’t miss out on an evening full of great music, charcuterie, and wine!

Under the Stars, on the Rocks | Chef Jennifer Carrol at Skyline Lodge
2025-08-12 18:00 | Oak Steakhouse at Skyline Lodge, 470 Skyliine Lodge Road, Highlands, NC, 28741, United States
Enjoy a one-of-a-kind dining experience with our premier guest chef dinner series, “Under the Stars, On the Rocks”.
Hosted at Skyline Lodge against the stunning Blue Ridge Mountains, this event offers an al fresco steakhouse dining experience. Featuring collaborations with renowned chefs from around the country and Oak Steakhouse’s culinary team, each four-course meal will be family-style and is unique and personalized to the guest chef.
For $175 per person, including beverage pairings, plus tax and gratuity.

Wine, Women and Song at On the Verandah
2025-08-18 18:00 - 21:00 | On the Verandah, 1536 Franklin Rd, Highlands, NC, 28741, United States
Join us at On the Verandah for Wine, Women and Song with host Lisa Rankin. An event celebrating the anniversary of the 19th Amendment and the power of women’s voices, both literal and figurative.
It will be an evening that blends live music, wine, art, and activism into a free-form celebration of women’s rights and creative expression.

Sip & Sign | Meet Author Richard Betz at Highlands Wine Shoppe
2025-08-22 16:30 - 19:00 | Highlands Wine Shoppe, 269 Oak St, Highlands, 28741, United States
Join us at Highlands Wine Shoppe for a very special evening celebrating local author Richard Betz and the release of his latest book, Continental Divide—a stunning collection of poems inspired by the natural bounty, wildlife, and deep personal connections that make our corner of North Carolina so extraordinary.
The evening will feature:
Wine & charcuterie pairings (including a nod to our very own mention in the book!)
Readings and reflections by the author
A warm gathering of friends, both new and old

Pups and Pints at Highlands Smokehouse
2025-08-23 12:00 - 15:00 | Highlands Smokehouse
Get ready for a tail-wagging good time!
Browse unique finds from local vendors selling handcrafted dog apparel, gourmet treats, and more. Enjoy live music, delicious BBQ, a full bar and meet adorable, adoptable puppies brought by the Cashiers-Highlands Humane Society-you might just meet your new best friend!
Bring your dog, bring your friends, and raise a pint to a great cause.
See you there!

4th Annual Sunday Supper: South of France at The Farm at Old Edwards
2025-08-24 18:00 | The Farm at Old Edwards, 336 Arnold Road, Highlands, NC, 28741, United States
Sit down for Sunday supper with Chef Joe Cash of Scoundrel in Greenville, SC. His signature voluptuous French brasserie dishes guarantee to please guests with a mashup of familiar Southern Sunday Supper dishes, each re imagined with distinctive ingredients, herbs, and spices to deliver surprising and delightful bursts of flavor. Live music will help create a joyous ambiance for the 4th Annual Sunday Supper at The Farm at Old Edwards.
Located in the heart of downtown Greenville, Scoundrel is the culinary creation of Chef Joe Cash, who returned to his hometown in 2022 to open his first solo venture. With a focus on French-inspired cuisine and a commitment to using the finest local and seasonal ingredients, Scoundrel has quickly become a standout in the dining scene. The restaurant has earned national recognition, being named one of Esquire’s ‘Best New Restaurants in America’ for 2023 and receiving a semifinalist nomination from the James Beard Foundation for ‘Best New Restaurant.’ Scoundrel offers an inviting yet elevated dining experience that blends modern techniques with classic flavors, all within a warm and intimate setting.

Summer Picnic at Highlander Mountain House
2025-08-30 11:30 - 15:00 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Highlander Mountain House kicks things off with a Summer Picnic featuring a cookout-style menu takeover by The Ruffed Grouse, live bluegrass music, and specialty cocktails.

Labor Day Weekend Oyster Roast at Highlander Mountain House
2025-08-30 15:00 - 17:30 | Highlander Mountain House, 270 Main St, Highlands, NC, 28741, United States
Celebrate Labor Day Weekend with a lowcountry oyster roast with fresh Gulf oysters from our friends at Pelican Oyster Company.
Ticket includes all you can shuck oysters, your first beer from Munkle Brewing, and live bluegrass on the porch from Daniel Ullom + Friends.

HF&W | The Barn Ramble at Flat Mountain Farm
2025-09-15 19:00 - 21:30 | Flat Mountain Farm, 1359 Flat Mountain Road, Highlands, 28741, United States
A Highlands Food & Wine Event
Dust off your toe tappers, get ready to take a twirl on the dance floor and head to Flat Mountain Farm in Highlands for The Barn Ramble, Saturday November 14 from 7:00–9:30 pm.
Enjoy performances by Nashville’s Sam Morrow, light bites by Little Secret, and beer, wine, and Blade & Bow signature cocktails.

Under the Stars, on the Rocks | Chef Kevin Maxey at Skyline Lodge
2025-09-16 18:00 | Oak Steakhouse at Skyline Lodge, 470 Skyliine Lodge Road, Highlands, NC, 28741, United States

7th Annual Oyster & Seafood Fest at The Farm at Old Edwards
2025-09-28 16:00 - 20:00 | The Farm at Old Edwards, 336 Arnold Road, Highlands, NC, 28741, United States
September brings the last of summertime celebrations but, fortunately for oyster lovers, it also means the return of their favorite shellfish. Passed hors d’oeuvres, a lavish raw bar, and creative cocktails will set the stage for deliciousness to follow in this fun, interactive seafood dinner with live music at The Farm at Old Edwards.
The culinary expertise from the Old Edwards Chef team will be joined by Lowcountry Oysters, and Chef Sara Prezioso of Charleston Bay Gourmet. They will be joined by Kathyrn Fitzgerald of Regina’s in Asheville and Chemist Spirits will present several curated cocktails for guests and live music to enjoy throughout the evening. Craft beer and fine wine will also be served.

Under the Stars, on the Rocks | Chef Sam Diminich at Skyline Lodge
2025-10-07 18:00 | Oak Steakhouse at Skyline Lodge, 470 Skyliine Lodge Road, Highlands, NC, 28741, United States
Enjoy a one-of-a-kind dining experience with our premier guest chef dinner series, “Under the Stars, On the Rocks”.
Hosted at Skyline Lodge against the stunning Blue Ridge Mountains, this event offers an al fresco steakhouse dining experience. Featuring collaborations with renowned chefs from around the country and Oak Steakhouse’s culinary team, each four-course meal will be family-style and is unique and personalized to the guest chef. For $175 per person, including beverage pairings, plus tax and gratuity.
Chef Sam Diminich, originally from Myrtle Beach, SC, comes from a deep culinary lineage and sharpened his craft at the Culinary Institute of America under the guidance of renowned Chef Georges Perrier. After immersing himself in the Charlotte culinary scene and learning from esteemed local chefs, he gained recognition with a victorious appearance on Food Network’s “Beat Bobby Flay” and later launched successful ventures like “Your Farms Your Table” and Restaurant Constance, earning him a 2025 James Beard Foundation Award semifinalist nod. Beyond the kitchen, Sam is committed to supporting fellow food professionals through non-profit organization, Ben’s Friends.
