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Sarah & Will

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    Things To Do

Things To Do

We're so excited to share one of our favorite places with our favorite people. Highlands & Cashiers have lots to offer for a fun filled weekend ranging from endless outdoor activities to music, art and of course - wining and dining downtown. Below are some great recommendations and a good starting point for a great weekend! If you have any questions, please ask!

Thursday Night Carolina Concert Series

In Trailborne Hotel's backyard, Juan Holladay will be playing music as part of the Carolina Concert Series! Grab a cocktail and catch some tunes.

Friday Night Live

Town Square Highlands,

Every Friday night, downtown Highlands has live performances in the summer. These free concerts offer the chance to hear some of the finest music the region has to offer.

Saturday Morning - Mountaintop Arts & Crafts Festival

Downtown, a two day, two weekend event that brings over 80 artisans from the region to Highlands for demonstrations, fine art, crafts, entertainment!

Whiteside Mountain Trail

NC 28741

Our favorite hike in the area! This is a 2 mile loop and takes about 1.5 hours. Just long enough to deserve a beer in town afterwards!

Secret Falls Trail Head

Big Creek Road, Highlands, NC 28741

Great little hike that brings you to a swimming hole and waterfall.

Scaly Mountain Hike

A little over 2 hours from beginning to end, this 4 mile hike is a little more challenging than your everyday walk in the park. The hike is worth the view you find at the summit!

Glen Falls Hike

About an hour and half from beginning to end, this 2.5 mile hike is one of the area's most popular.

Chinquapin Mountain Trail

NC 28734

Roughly 1 hour and 40 minutes from beginning to end, this 3.1 mile trail heads out from Glen Falls trailhead and takes you to the top of Chinquapin Mountains at about 4,200 feet of elevation.

Fly Fishing, Water Rafting

Highlands Chamber is a great resource for all things, including outdoor activities. For those on the more adventurous side, take a peak at all guides tours!

The Bascom: Center for the Visual Arts

323 Franklin Road, Highlands, NC 28741

While we'll be celebrating at the Bascom Saturday night, it's a much different experience during the day! Come tour the grounds or take one of the pottery classes onsite - we'll make sure the pieces are fired and sent your way safely!

Sky Valley Country Club

568 Sky Valley Way, Sky Valley, GA 30537
, (706) 746-5302 ext. 1

Semi private golf course open to the public.

Highlands Wine Shoppe

269 Oak Street, Highlands, NC 28741

Needless to say, one of our favorite places in town. They have a wonderful assortment of wines, snacks, and the best lawn in town to listen to live music or play a game of cards.

The Wine Garden & Rooftop Terrace at Old Edwards

420 Main Street, Highlands, NC 28741

Favorite outdoor patio perfect for leisurely lunch located at the Old Edwards Inn. If the wait is to long, opt for the rooftop terrace for lunch! Both great options.

Highlander Mountain House & The Ruffed Grouse Tavern

270 Main Street, Highlands, NC 28741

Located at the Highlander Mountain House, best place in town for brunch and also live music on Thursday nights. Sitting outside is a must!

Highlands Supper Club

Highlands, NC 28741

The renovated old cabin is up the hill past Trailborn hotel, it's a treat for dinner!

Four65 Woodfire Bistro + Bar

465 Main Street, Highlands, NC 28741

Perfect place to grab a casual pizza and caprese, and an option for larger groups!

The Ugly Dog Public House- Highlands

294 South 4th Street, Highlands, NC 28741

A staple in Highlands, best place for local pub fare. Great for a late night brew, along with it's sister location, The High Dive for late night.

Whiteside Brewing Company

128 North Carolina 107, Cashiers, NC 28717

Great brewery with great food the next town over in Cashiers! Pop over for a brew after hiking, home shopping, or grabbing BBQ across the street!

Oakleaf Flower & Garden

330 2nd Street, Highlands, NC 28741

Oakleaf is the area's premier garden and lifestyle shop showcasing unique gems and historical pieces. Don't forget to stop and smell the roses!

Mountain Fresh Grocery

521 Main Street, Highlands, NC 28741

Wanting a quick bite, breakfast sandwich, or a snack for a hike? Look no further. Great selection of local produce, wine, and casual meals. A staple in town!

Canyon Kitchen

Cashiers, NC

Wonderful dinner spot in Cashiers.

The Secret Garden

208 North 5th Street, Highlands, NC 28741

Great sandwhiches, lunches, and to go food! It's tucked away, hence - secret!

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