Name: Reggie Headen & Friends
Start: 2026-10-24T20:00:00.000-04:00
End: 2026-10-24T20:00:00.000-04:00
Location: 5 Walnut Wine Bar

Reggie Headen & Friends plays 5 Walnut Wine Bar on Saturday, October 24 at 8:00 PM. Easy one to plan a night around.

This downtown Asheville spot keeps things relaxed and approachable rather than pretentious, with most shows running no cover and wine by the glass starting at five bucks. The room only holds about 75, so grab one of those window bar seats early if you can, and the adjoining cheese shop means you can snag a board without leaving the building.

5 Walnut Wine Bar is a downtown Asheville listening room on Walnut Street, hosting live music seven nights a week. Jazz, swing, gypsy jazz, and acoustic singer-songwriter shows fill the small wine bar most evenings.

Locals dig 5 Walnut for its friendly bartenders, generous pours, and the relaxed atmosphere that’s perfect for catching up with friends or winding down after a long day. It’s also known for live music most nights, from jazz and blues to Americana, which adds just the right vibe without overpowering your conversation. Whether you want to sip a glass of crisp white or a bold red, this spot feels like a sweet escape right on Walnut Street.

5 Walnut Wine Bar

Looking for the best bars in Asheville? Find cocktail lounges, dive bars, rooftops and live music spots downtown, on the South Slope and in West Asheville. Downtown, Little Jumbo pours cocktails in an old grocery on Broadway, The Crow and Quill stocks more than 800 whiskeys behind an easy-to-miss door on Lexington Avenue, and The Workshop Lounge has jazz inside The Foundry Hotel. Capella on 9 serves drinks with mountain views atop the AC Hotel, District 42 sits on Pack Square, and Cork & Keg pours wine inside The Weinhaus on Patton Avenue. 5 Walnut Wine Bar has live jazz and acoustic sets most nights, and Fitz and the Wolfe runs three rooms on Battery Park Avenue. On the South Slope, Banks Ave. hosts drag shows and DJ nights, and Sovereign Kava pours kava on Biltmore Avenue. Haywood Road in West Asheville has The Low Down under The Hop, wine and vinyl at Potential New Boyfriend, and late shows at The Odd and Fleetwood's. Out east, The Social is a neighborhood pub on Tunnel Road, and Town Pump Tavern and White Horse anchor downtown Black Mountain. When the night's over, call AVL Ride for the trip home.

Bars in Asheville, NC: Nightlife, Lounges and Music Halls

Experience the rich flavors of Asheville, NC’s wine and spirits scene, featuring local wineries, craft distilleries, and stylish wine bars. Whether you’re a wine enthusiast, cocktail aficionado, or simply looking to savor small-batch spirits, Asheville offers a diverse range of tasting experiences and expertly crafted beverages. Explore vineyard tours, distillery tastings, and cozy bars offering innovative cocktails made with local ingredients. Find the perfect spot to unwind, celebrate, or discover new favorite drinks in this dynamic southern city known for its vibrant beverage culture and craftsmanship.

Reggie Headen & Friends

The Scoop