DAY ONE 

2pm—A Caffeinated Pick-Me-Up & Planning Session 

If you’re just getting to town, consider taking a bit of time to plan your trip and make the most of your visit. Head to Battle Cat or Tiger Bay Café in West Asheville for an expertly prepared coffee drink (I always get an iced matcha latte) and get your bearings. If you already have some ideas in mind for your visit, then you can use this time to sit and journal or sketch, while picking up inspiration from the alternative art on the walls. 

3pm—River Arts District: Intro Stop 

Just across the French Broad River is the River Arts District (RAD), Asheville’s creative hub with dozens of working artists. While there’s enough to see and do here to fill the whole weekend (and I recommend the Studio Stroll on Saturdays), you can get your feet wet with a visit to the Art Garden, where several local artists are represented (including my daughter, Alex Stilber, who focuses on figurative expressionist painting). Nearby is Tyger Tyger Gallery as well as the Modern Muse, one of the newest additions to the RAD. Consider taking a class at the Asheville Print Studio and Gallery. 

7pm—Drum Circle & Treat 

If you’re feeling inspired, keep the energy flowing with a trip to Pritchard Park in downtown Asheville and listen to or join the drum circle, which forms on Friday nights. Grab dinner afterward at Tupelo Honey Café right on the square. 

9pm—Live Music 

Check out some of the local live music options at The Hound (the blues and jazz musician Reggie Headen plays most Fridays), located in a renovated Greyhound bus station on Tunnel Road, just a few minutes from downtown. There’s indoor and outdoor seating, as well as a menu of some local favorites and often a food truck. 

11pm—Late-Night Drinks 

For a unique experience, and the chance to mingle with a few locals, check out the Pink Moon Craft Cocktail Bar, located behind Double Crown in West Asheville. It’s a speakeasy type of place and you need a one-time access code, which you can find on Pink Moon’s Instagram stories. 

Live music at The Hound

DAY TWO 

10am—Museum 

Start your day with a trip to the Asheville Art Museum. Recently renovated, and located on Pack Square, the museum hosts many impactful art shows and provides opportunities to local organizations and aspiring young creatives in the area. And make sure to check out the gift shop, which offers a lot of cool treasures. 

Noon—Lunch 

Stop for lunch at Hemingway’s Cuba, one of my favorite rooftop restaurants. Here you can have a bite with stunning mountain views and enjoy a refreshing mocktail or cocktail. The perfect photo ops happen at sunset. If you’re looking for a treat afterward, head down to Kilwins for an ice cream. And if you have extra time, stop at Bella’s of Asheville on Battery Park to see if any new artists are showing. 

2pm—RAD Second Saturday Studio Stroll 

On the second Saturday of each month, the River Arts District holds the Second Saturday Studio Stroll with live music, demos, workshops, wine tastings, food and more. They have a trolley you can ride for free to take you to different areas of the mile-long district. If you’re visiting on one of those days, this is a must-see event. Make sure to check out Jeffrey Burroughs: The Jewel of Asheville for one-of-a-kind pieces (I recently stopped by their gallery to discuss having a custom ring created around a stone that I purchased at a gem show.) 

5pm—Dinner 

Around the corner from Jeffrey Burroughs is The Bull and Beggar, a popular restaurant that has a creative menu and uses a lot of seasonal, local ingredients. After dinner, walk to Wedge Brewing Co on Paynes Way for a Vadim Bora stout, described as “intensely decadent” and named after a local painter, sculptor and gallery owner. 

8pm—Music 

For great live music, head to Guitar Bar in the River Arts District. You can relax and check out the many guitars that line the walls, some of them signed by incredible rock stars. Another option is the Great Wild Nowhere, which is right next door and has DJs spinning until midnight, and some nights, live bands. 

Artist demo at the River Arts District

DAY THREE 

11:30am—Brunch 

If this is your last day in town, you might have to spend a bit of the morning packing up—and hopefully, you’ve got some new art to take home with you. Plan on brunch to give yourself the time you need. I recommend Laughing Seed Café, a downtown restaurant that serves vegan and vegetarian dishes and has great outdoor seating on Wall Street for people watching.