Things To Do
Highlands Wine Shoppe
A cute stop right in town. You can do a casual, self-guided wine tasting and put together a simple charcuterie board. There’s nice outdoor seating on the front lawn.
Madison's Restaurant
A go-to for a nicer dinner in town, located at the Historic Old Edwards Inn. Worth getting there a little early for a drink at the bar or Hummingbird Lounge. The same chef is behind our wedding menu — so if you don’t make it here, you’ll still get a taste!
Four65 Woodfire Bistro + Bar
For your wood-fired pizza fix! Right on Main Street.
On The Verandah
A more classic, slightly tucked-away spot with a great view over the water. Known for elevated options. Nice choice if you want a quieter dinner and a pretty setting. About 2 miles from the historic inn.
The Wine Garden at Old Edwards Inn
Outdoor spot at OEI. A relaxed setting for wine or cocktails.
The Rooftop Terrace at Old Edwards Inn
A small rooftop patio located at OEI with nice views, cocktails, and light bites.
Oak Steakhouse
A great option for a more elevated dinner, about 10 minutes (~4 miles) outside of town at Skyline Lodge. Classic steakhouse menu plus really nice views of the mountains.
Mountain Fresh Grocery
Part market, part casual restaurant right at the end of Main Street. Good for coffee, breakfast, or an easy lunch, plus grab-and-go options. Also a solid spot to pick up wine, beer, snacks, or anything you might need.
Calders Coffee Cafe
Go-to spot for coffee and a quick breakfast right on Main Street.
Highlands Smokehouse
A classic, no-frills BBQ spot that’s been around forever. Good for a casual meal inside or out on the deck. Low-key option for dine-in or takeout. A little over a mile from the historic inn.
The Ugly Dog Public House- Highlands
A laid-back, reliable spot right in town for a casual meal or drink. Easy place to grab a table with a group and hang out for a while.
Whiteside Brewing Company - Cashiers
About 25 minutes away in Cashiers. Good spot to hang outside, grab a beer, and get a casual bite if you’re planning to explore that area.
The Bascom: A Center for the Visual Arts
A really nice daytime stop. It’s set on a former horse farm and has rotating exhibitions, plus a sculpture trail and pretty grounds to walk around. Easy to pop in for an hour or spend more time if you’re into it. It’s open to the public (and free), so you can just stop by — no tickets need, but be sure to check the hours before heading over.
Highlands Biological Station
An easy, low-key outdoor stop without committing to a full hike. It’s a peaceful walking area with native plants, shaded paths, and a few different garden sections. It’s been around since the early 1960s and is part of the Highlands Biological Station, originally set up to support research and conservation of the region’s plant life.
Whiteside Mountain Trail
One of the most popular hikes in the area. It’s about a 2.5-mile loop with great views, and a pretty manageable option without doing anything too intense. Plan for a small day-use fee and a short drive from town.
Cliffside Lake Trail
A good, easy option if you want something more relaxed. The loop around the lake is mostly flat, with the option to add a short uphill section for a nicer viewpoint. Close to town.
Sunset Rock Trail
A quick, easy walk just outside of downtown. It’s about a half-mile up a gravel path to a wide rock overlook with views over town.