Free, family‑friendly concert series runs March through October in Downtown Whiteville
WHITEVILLE, NC — Spring is almost here and so is Music in the Alley. The Whiteville Downtown Development Commission is bringing back its free summer concert series, offering eight months of live performances in the heart of downtown.
The 2026 season runs March through October, featuring a mix of returning crowd favorites and new artists making their Alley debut. Concerts are held on select Thursdays from 7:00 p.m. to 9:00 p.m. at 719 S. Madison Street, Whiteville, and are open to all ages.
Finding The Alley
The Alley sits directly beside Collier’s Jewelers on South Madison Street, giving concertgoers an easy landmark to spot. If you’re heading downtown, look for the familiar storefront and you’ll find The Alley just steps away — a convenient, central location for an evening of live music.
What First‑Time Visitors Can Expect
Stepping into The Alley feels like entering a tucked‑away pocket of downtown charm. Soft sun drapes stretch overhead, catching the evening breeze, while fans keep the air moving on warm nights. As the sun sets, party lights sway gently from one side of the alley to the other, casting a warm glow that makes the space feel festive and intimate.
Visitors will find seating scattered throughout the space, and many regulars bring their own fold‑out chairs to settle in for the evening. On select dates, local food trucks set up nearby, offering everything from snacks to full meals, and community vendors are often invited to join the fun. It’s a relaxed, come‑as‑you‑are atmosphere where families, friends, and newcomers can unwind and enjoy live music under the lights.
Organizers say this year’s lineup showcases a wide range of musical styles from country and acoustic sets to original music and classic covers giving residents and visitors plenty of reasons to gather, relax, and enjoy the sounds of summer.
2026 Music in the Alley Lineup & Performer Backgrounds
March 19 — Crenshaw Trucking Band (Acoustic Set)
A longtime regional favorite, the Crenshaw Trucking Band is known for its easygoing blend of country, Americana, and acoustic storytelling. Their stripped‑down sets have become a signature part of the Alley’s opening and closing shows.
April 16 — Jeffery Simmons
Jeffery Simmons is a smooth‑voiced singer‑songwriter whose sets often mix soulful originals with familiar acoustic favorites. He’s built a steady following across southeastern North Carolina for his warm stage presence and laid‑back sound.
April 30 — Skyler Whitfield
Skyler Whitfield brings an energetic mix of modern country and upbeat covers. Known for his crisp vocals and crowd‑friendly style, he’s become a popular performer at festivals and outdoor venues throughout the region.
May 7 — Daren Wheeless
Daren Wheeless is a versatile guitarist and vocalist who blends classic rock, folk, and country influences. His acoustic performances are known for their clean musicianship and nostalgic song selections.
May 21 — Brian Roessler
Brian Roessler is a seasoned solo artist whose performances highlight thoughtful songwriting and mellow acoustic arrangements. His sets often feature a mix of originals and reimagined classics.
June 4 — Logan Crosby
Logan Crosby is an emerging country artist gaining attention for his polished vocals and radio‑ready sound. His performances combine contemporary country hits with heartfelt originals.
June 18 — Rhett Drew
Rhett Drew brings a modern country edge with a mix of upbeat tracks and soulful ballads. His strong vocals and engaging performance style have made him a rising favorite at coastal venues.
July 16 — Allie McDowell
Allie McDowell is a singer‑songwriter known for her bright tone and heartfelt acoustic performances. Her music blends country, pop, and folk influences, appealing to a wide range of listeners.
July 30 — Johnny Stone – Back Home with Southern Songs
Johnny Stone delivers a nostalgic, Southern‑inspired set that celebrates classic country storytelling. His “Back Home with Southern Songs” performances highlight traditional favorites and warm, familiar melodies.
August 20 — Lane Ward
Lane Ward is a country and Americana artist with a rich, resonant voice and a talent for connecting with audiences. His sets often feature a mix of originals and timeless covers.
September 17 — Luke Kiser
Luke Kiser is known for his smooth vocals and contemporary country style. His performances blend heartfelt originals with popular modern hits, making him a strong fit for late‑summer crowds.
October 17 — Crenshaw Trucking Band (Acoustic Set)
Closing out the season, the Crenshaw Trucking Band returns with another acoustic performance, a tradition that has become a favorite way for locals to wrap up the Alley’s concert year.
A Community Tradition
Music in the Alley has grown into one of Downtown Whiteville’s most anticipated seasonal traditions, drawing families, friends, and visitors to enjoy live music in a relaxed outdoor setting. Organizers encourage attendees to “save the dates, and make plans to enjoy the sounds of summer,” noting that the series is designed to bring people together and support a vibrant downtown atmosphere.
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