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October 11, 2025
Cashiers, NC

Sydney & William

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Things To Do

Cashiers Leaf Festival

Cashiers Leaf Festival

160 Frank Allen Road, Cashiers, NC 28717

The Cashiers Valley Leaf Festival is a must! It takes place at The Village Green and features around 90 artisans showcasing handcrafted wood, pottery, jewelry, and other unique crafts. The festival also includes live music, food trucks, and family-friendly activities, making it a fun way to enjoy the fall colors and local art scene. The event runs from Friday through Sunday, with free admission, so it's a great stop for everyone​

Highlands

Highlands

Highlands, NC 28741

Downtown Highlands is a super charming mountain town just a short drive from our wedding venue! It’s got everything—cute boutique shops, art galleries, cozy cafes, and some amazing local restaurants. Whether you want to wander through the shops, grab a coffee, or hit up a trail for some fresh mountain air, it’s the perfect spot to soak up that North Carolina magic. If you’ve got some free time, definitely check it out!

Whiteside Brewing Company

Whiteside Brewing Company

128 State Route 107, Cashiers, NC 28717

Whiteside Brewing Company is one of our favorite spots! Will and I went with his parents, and we absolutely loved it (the Brussels sprouts are a must-try!). It’s basically right in the backyard of the Wells Hotel and super close to Hotel Cashiers, so it’s an easy and fun spot to grab a drink or bite to eat. Whether you’re into craft beers or just want to relax on their patio with some good food, it’s a great place to hang out.

Whiteside Mountain Hike

Whiteside Mountain Hike

170 Deville Drive, Highlands, NC 28741

The Whiteside Mountain hike is one of my favorites, and it’s only about a 20-minute drive from Cashiers! It’s a moderate 2-mile loop with some steep sections, but I’ve hiked it many times, and the views are absolutely worth it—especially in the fall when the leaves are changing. You get these amazing panoramic mountain views at the top that are just stunning this time of year. If you’re up for a little adventure, it’s a must-do!

Sunset Rock- Highlands Cashiers Land Trust

Sunset Rock- Highlands Cashiers Land Trust

131 Highlands Gate Drive, Highlands, NC 28741

Sunset Rock is another great spot, just about 10 minutes from Cashiers and 1 minute from Highlands! Even when it’s not sunrise or sunset, the views are still so pretty. Jay, Liv, (groomsman & bridesmaid) and I went earlier this year, and it was such a peaceful and beautiful place to hang out. It’s a short, easy walk up, and once you’re there, you’ll have a perfect view of the mountains and the surrounding area. If you’re looking for a quick, scenic stop, this is it!

Sapphire National Golf Club LLC

50 Slicers Ave, Sapphire, NC 28774

Located in the Sapphire Valley, this is the only fully public 18-hole golf course in the region. It features dramatic elevation changes and stunning mountain views. The course underwent a significant renovation and offers a memorable experience for all skill levels. You can book tee times directly without needing to be a member or guest of any resort.

Red Bird Golf Links

67 Cherokee Trail, Sapphire, NC 28774

This is a 9-hole executive course in the Sapphire area, designed for a more casual, accessible round. It's ideal if you're looking for a shorter game while enjoying the mountain surroundings.

Highlands Aerial Park

Highlands Aerial Park

9625 Dillard Road, Scaly Mountain, NC 28775

Highlands Aerial Park is such a fun spot, and I’ve been there before! It’s perfect if you’re looking for some adventure. They’ve got zip lines, and one of them is over 1,500 feet long, giving you amazing views of the canopy and mountains as you fly through the trees. They also have a giant swing, hiking trails, and a ton of other outdoor activities. Whether you’re up for a thrill or just want to explore the trails, it’s an awesome way to experience the area from a new perspective!

The Orchard Restaurant

905 North Carolina 107, Cashiers, NC 28717

A cozy, rustic atmosphere in a historic farmhouse setting. It’s perfect for a farm-to-table Southern dining experience, complete with views of the apple orchard. They have both indoor and outdoor dining options, making it a great spot for a memorable dinner​

The Library Kitchen & Bar

184 Cherokee Trail, Sapphire, NC 28774

Nestled within the heart of contemporary American cuisine, our restaurant is more than a mere dining experience – it's an exploration of the senses, an embodiment of authentic luxury, and a testament to the power of genuine connection. Crafting each dish with the freshest natural ingredients, Michelin star-trained and award-winning Chef Johannes Klapdohr transforms simplicity into artistry. This upscale culinary journey remains grounded in authenticity, ensuring every guest feels warmly welcomed.

Slab Town Pizza

45 Slab Town Road, Cashiers, NC 28717

Slab Town Pizza in Cashiers is a great spot for casual dining. It’s known for its delicious build-your-own pizzas and calzones, made with fresh ingredients and customizable toppings. The relaxed atmosphere makes it perfect for groups looking for a laid-back meal. It’s a great choice for anyone craving some classic, comfort food in the area!

Ristorante Paoletti

440 Main Street, Highlands, NC 28741

A long-standing favorite for Italian cuisine, offering dishes like sautéed NC rainbow trout and homemade tortellini. It’s perfect for a cozy, upscale dinner.

Madison's Restaurant

445 Main Street, Highlands, NC 28741

Located in the Old Edwards Inn, this spot is great for a refined Southern meal with garden-fresh ingredients and outdoor seating in the Wine Garden.

The Rooftop Terrace

455 Main St, Highlands, North Carolina 28741

The Rooftop Terrace at Old Edwards Inn is one of my favorite brunch spots! I had a fantastic meal here with Jay (groomsman), Liv (bridesmaid), and Gorman (groosman)and it’s the perfect place for a sunny day. The terrace overlooks Main Street, and the fresh, locally sourced dishes make it an incredible spot to relax and enjoy the mountain air while dining​

Wild Thyme Gourmet

343-D Main Street, Highlands, NC 28741

Wild Thyme Gourmet is a Highlands gem, known for its relaxed atmosphere and diverse menu. It offers everything from fresh seafood dishes to vegetarian options, making it a versatile choice for lunch or dinner. With its cozy setting and delightful outdoor patio, it’s a perfect spot to enjoy a meal and unwind in the heart of town​

Mountain Fresh Grocery

521 Main Street, Highlands, NC 28741

Mountain Fresh Grocery is hands down one of my favorite spots for lunch—I’ve lost count of how many times I’ve eaten there! Even though it’s a grocery store, it offers a fantastic selection of made-to-order sandwiches, salads, and Southern comfort dishes. It’s the perfect place for a casual, delicious meal in a relaxed setting. Whether you grab a coffee, a quick bite, or stock up on specialty groceries, it’s a must-visit if you’re in Highlands​

Sweet Treats

411 S Fourth St, Highlands, North Carolina 28741

Sweet Treats is a go-to spot for ice cream in Highlands, and I absolutely love their soft serve! It’s a classic place to grab a cone and enjoy a sweet break while exploring the town. Whether you’re craving a quick treat or looking for something nostalgic, their soft serve is always a perfect choice. I know it’ll be October, but I had to plug it anyways

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