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Top Highlands Events & Festivals

Highlands is a quaint mountain town nestled in the southern Blue Ridge Mountains of North Carolina. Voted one of the “Best Small Towns in the South”, Highlands is a bucket-list vacation destination with an abundance of natural beauty, outdoor recreation, shopping & dining, arts & culture, and coveted music and culinary festivals that draw crowds year-round.

Highlands Festivals, Inc. host two of Highlands most celebrated festivals, the Bear Shadow Festival in spring, and the Highlands Food & Wine Festival in fall.

Bear Shadow Festival

April 29 – May 1, 2022
Winfield Farm, Highlands, NC

The Bear Shadow Festival is a 3-day annual springtime festival at Winfield Farm, 7 miles from downtown Highlands. Spend a weekend in an intimate mountain setting on the Highlands-Cashiers Plateau with immersive day time adventure experiences, music-inspired films and clinics, and a talented line-up of top artists and renowned songwriters.

Your Bear Shadow Base Camp pass includes beer, wine and non-alcoholic beverages at the Bear Den, and access to craft stands and a food court with local vendors serving Highlands favorite foods. VIP and Platinum passes are also available (but very hard to come by!). Complimentary shuttles run throughout the weekend to and from Founders Park in downtown Highlands to the base camp at Winfield Farm.

This highly-anticipated Highlands festival is named after the “Shadow of the Bear” that appears as the sun sets behind Whiteside Mountain in fall and early spring, best viewed from the Big View Scenic Overlook on Route 64, 6 miles from downtown Highlands.

Highlands Food & Wine Festival

November 10 – November 13, 2022
Downtown Highlands, NC

The Highlands Food & Wine Festival is a four day annual festival in downtown Highlands, one of the finest small town culinary events in the Southeast, and a well celebrated Highlands tradition at 4118 feet. Immerse yourself in an elevated weekend of specialty dinners at Highlands best restaurants, unique food and wine experiences, an awesome line-up of live music from nationally acclaimed musicians, and a chance to mingle with the finest winemakers, connoisseurs and culinary talent in the Southeast.

The festival kicks off on Thursday evening with a Grand Tasting at Founders Park followed by the Truckin’ event on Friday, with some of the best food trucks in South Carolina. The Main Event on Saturday features oyster roasts, small tasting plates from local and regional chefs, hand crafted cocktails and wine tastings from award-winning vineyards. The Sunday Shindig is the grand finale of the festival, a brunch event with a Bloody Mary bar, spiked coffees, savory small plates to sample, and laid-back live music.

From vibey beer gardens, food trucks and craft beer to fine wines from around the world and culinary appearances from world-class featured chefs, you’re in for a fabulous, fun, and flavorful experience in the beautiful Blue Ridge Mountains.

Please note that all events are 21+ and a full COVID-19 vaccination or negative COVID-19 test result is required to attend the Highlands Food & Wine Festival 2022.

Where to Stay in Highlands, NC

Tickets for these highly coveted Highlands events sell out quickly, as do hotel rooms and vacation homes, so advanced planning is required! Highlands Vacation Rentals offer a diverse portfolio of vacation cabins and homes on the Highlands-Cashiers Plateau with a welcoming home away from home for every size, style, and budget. Our walk to town rentals are perfect to stay close to the festivities and events in the heart of Highlands.

The Inn at Mill Creek
The Inn at Mill Creek is located on the banks of scenic Mill Creek in the heart of downtown Highlands, only two blocks from Highlands Main Street. The inn offers a selection of luxury pet-friendly suites with modern interiors, plush amenities, fireplaces, and balconies overlooking Mill Creek. Large groups can book multiple suites to stay close together under one roof.


Owl’s Den
Studio Tiny Home, Sleeps 2 Guests
Owl’s Den is a quaint and cozy tiny home only 3 blocks from Highlands Main Street. Featuring a king size bed, small kitchen, laundry and a screened in porch, Owl’s Den is a well-equipped and welcoming space to lay your head after a day of fun festivities.


Parrish Hill
2 Bedroom, 2 Bathroom, Sleeps 6 Guests
Parrish Hill is a secluded cottage less than a mile to downtown Highlands and Founders Park. This charming, quintessential mountain retreat accommodates up to 6 guests with an indoor fireplace for cool mountain evenings, an outdoor firepit for late night antics, and all the comforts of home.


Witt’s End
3 Bedroom, 3 Bathroom, Sleeps 6 Guests
This pet-friendly Highlands cottage is near Main Street and Flounders Park, a quaint mountain cottage with space to relax and unwind and a screened porch and multi-level deck with rocking chairs overlooking a rushing creek. Moss’s Mill Creek Cottage is right next door.


488 Main Street
3 Bedrooms, 4 Bathrooms, Sleeps 8 Guests
Indulge a little and book this 3-bedroom luxury apartment on Highlands Main Street. This luxury Highlands vacation rental boasts beautifully appointed designer interiors, plush amenities, a gourmet kitchen, and a secluded back deck with outdoor seating. All this just steps from the best dining, shopping and event attractions in Highlands, NC.

By |2022-10-02T14:04:31-04:00August 2, 2022|Blog|Comments Off on Top Highlands Events & Festivals

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