Live music in Millsboro, DE

Miss Maria leads a live class at the Seaford Library where children and their caregivers can enjoy music and movement together. The session offers a welcoming, family-friendly atmosphere with opportunities to participate and connect through rhythm and motion.

The Dirty Grass Players return to The Room at Cedar Grove for a dinner-and-concert experience. A $61 ticket includes the meal and the performance, with beverages available for purchase separately. Gratuity is not included, and all ticket sales are final. Hailing from Baltimore and active since 2015, this bluegrass group blends tradition with forward-looking energy. They move easily from extended improvisations to quick-fire classics, delivering tight harmonies, fresh original tunes, and adventurous solos that balance polish with a bit of grit. The band began with informal jams between founders Ben Kolakowski on guitar and Ryan Rogers on mandolin, quickly earning attention at home before taking their sound across the United States and Europe. Their festival history includes Grey Fox, DelFest, Dark Star Jubilee, ROMP, Bristol Rhythm & Roots, and the Rotterdam Bluegrass Festival. The current lineup features Connor Murray on bass since 2021 and the addition of banjo player Sam Guthridge in 2024. With two albums and numerous singles, their latest full-length, Shiny Side Up, was produced by Cody Kilby of the Travelin' McCourys and showcases bold playing and moody themes within a bluegrass framework. Industry praise has highlighted the record as a strong statement of the band’s place in the genre and its future. Their first single with the updated roster reimagines Jimi Hendrix’s Voodoo Child (Slight Return) with driving bluegrass power that nods to their roots while pushing into new territory.

Styx takes the stage with the momentum of a band still creating at full tilt, highlighting Circling From Above, the group’s 18th studio album. Across 13 songs and roughly 41 minutes from start to finish, the record explores the tension between technology and the natural world, folding longtime Styx trademarks into fresh ideas that build on The Mission and Crash of the Crown. The high‑energy lead track "Build and Destroy" sets the pace, while a loose throughline inspired by abandoned satellites and a starling-filled sky gives the music a vivid backdrop of ambition, fallout and hope. Seven members shape this chapter: founding guitarist and vocalist James "JY" Young, Tommy Shaw, original bassist Chuck Panozzo, drummer Todd Sucherman, and keyboardist and vocalist Lawrence Gowan, joined by Will Evankovich and Terry Gowan. Evankovich also produced and co-wrote alongside Shaw and Lawrence Gowan, underscoring a collaborative spirit the band credits for its latest creative surge. The album’s range is wide, from the baritone bite and searing solo of "King of Love" to the traded lead vocals in "Forgive," the Bond-tinged urgency of "Michigan," and the lift of "It’s Clear," a rare cut with three different lead voices. Elsewhere, "Everybody Raise a Glass" nods to stacked harmony guitars, "We Lost the Wheel Again" charges forward on muscular rhythm work, "Blue-Eyed Raven" blends Spanish guitar, mandolin and a whirlwind fiddle solo, and "The Things That You Said" and the reflective closer "Only You Can Decide" center personal choice and shared responsibility. Long celebrated as a powerhouse on the road for a quarter century, Styx pairs veteran cohesion with this new chapter for a concert experience rooted in storytelling, musical craft and enduring chemistry.

A weekly drag showcase at Freddie’s Follies features a dynamic cast of queens delivering captivating performances that celebrate creativity, individuality, nerve, and talent. There is a $5 cover at the door.

Answer the call of karaoke with a relaxed night of singing. Take the microphone, request the songs you love, and sing to your heart's content. It is straightforward, lively, and all about having fun.

The sixth annual Tucker Bike Benefit from Delmarva Riders begins with registration at Rommel Harley-Davidson Salisbury. Breakfast sandwiches will be available for purchase while DJ Mikey keeps the music going, followed by a police-escorted ride to Pittsville Volunteer Fire Department. There, the benefit continues with a cash bar and BBQ chicken dinners, a Chinese auction and a 50/50 raffle. Entertainment includes DJ Mikey along with a live performance by Rockoholics. Atlantis Tattoo will be offering tattoos, children can enjoy a complimentary bounce house, and vendors will be on site. All proceeds support a local Delmarva resident battling cancer.

An acoustic trio makes its first appearance at Jimmy's Grille in Dewey Beach with a live acoustic set to mark the debut.

Enjoy a real-time musical performance, with artists playing live for listeners.

This event features food, brews, and music at The Salted Rim.

Robin, Chuck and Paul are back with a set packed with classic rock from the 1960s through the 1990s, plus a little country in the mix. The trio will perform familiar tunes from across four decades.

Amy Helm sets the tone before Roger Daltrey steps into a close-up setting that blends beloved songs from The Who with deeper cuts and highlights from his solo work. Backed by a semi-acoustic, rock-driven band, he reimagines iconic tracks with a more personal touch while sharing candid stories that open a window into rock history. Expect surprises in the set, memorable tales from the road, and the unmistakable voice that helped define a generation, all delivered in a setting designed to feel up close and personal.

Freddie’s Follies turns Saturday nights into a weekly drag celebration, with a vibrant lineup of queens delivering crowd-pleasing performances. Each show spotlights personality, originality, boldness, and talent in equal measure. Admission is a $5 cover at the door.

Late night karaoke invites you to take the mic, request the songs you love, and sing your heart out. The setup is simple and focused on having fun.

Earth Jam Band brings a charged mix of classic rock and soul to Milton Theatre, powered by a lineup with deep ties to Delaware and the wider Delmarva scene. Since launching in 2023, the group has quickly become a favorite on the Delmarva beaches, drawing devoted fans with lively performances of songs by the Doobie Brothers, Creedence Clearwater Revival, The Guess Who, and Grand Funk, alongside soul staples from Stevie Wonder, The Spinners, and Marvin Gaye. The ensemble features Robbie LaBlanc on guitar and lead vocals, an international recording artist with past ties to Atlantic Records, Felix Cavaliere of the Young Rascals, and Bad River. Michael Daisey handles drums and shares lead vocals with credits that include Boyz of Summer, The Wise Guys, and The Five-8. Kevin Walsh takes lead guitar, known for work with Shytown, Melton Brothers, Stone Shakers, and Vinyl Shockley. Keyboardist Scott Schoem brings experience from DC Legends Nayas, Denise Henderson, The Fellas, Muskrat Lightning, and LCB. Longtime local musician Chatty Cooper adds percussion, with history in Scuzzy Frog, Vandy, Robbin Thompson, and Junior Wilson and Chatty. On bass and vocals, Todd Vukmanic anchors the groove with background in The Rutabagas, The Moonlight Mutts, and Red Eye Kings. Expect a high-energy show that channels the region’s rock roots with a set of familiar favorites and soulful grooves.

Step into the spotlight for karaoke and sing your favorite songs, from classic hits to current pop, or cheer on friends from the audience.

Sol will be at The Crab Barn in Millsboro, DE.

Fil Rhythm delivers a live performance at Signatures at Bayside.

Experience a lively spin on bingo where the soundtrack sets the pace. Each game blends classic number calling with tracks that span decades and styles, with prizes, surprises, and the occasional sing-along keeping the energy high. It is free to play, and winners take home rewards. Ink dabbers are supplied, along with full-color paper bingo cards, so everything needed is ready at the table. Expect a wide mix of rounds, and do not be surprised if a memorable crowd moment breaks out and the spotlight suddenly lands on your table.

Step up to the mic and take the spotlight at karaoke. Sing beloved classics, lean into your pop-star side, or cheer on friends from the audience. The focus is on having fun.

A welcoming get-together for ukulele players and other acoustic musicians, with time to learn together, play, sing, and strum.

Lefty’s Alley & Eats hosts a weekly Tunes & Trivia night led by Jersey John, featuring rounds like Name That Tune, general trivia, and Jersey Feud. It is free and open to all ages, with prizes available. Expect music-themed challenges, plenty of laughs, and a chance to enjoy food and drinks while you play.

Nate McCormick hosts a weekly acoustic open mic at The Listening Booth that welcomes participants of all levels. It is fully unplugged, with no drum kits or amplifiers, and while original songs are encouraged, cover tunes are welcome as well. Sign ups are available, followed by live performances. There is no admission fee, though a two drink minimum applies. The space offers a complete sound setup and an upright piano, and loaner guitars are available for those who need one. Each week features a songwriting prompt, and performing a new song based on it the following week earns a complimentary drink. Tickets or RSVPs are not required.

Midweek at The Groove Restaurant brings the aroma from the kitchen and a lively twist on music bingo. Funky Music Bingo keeps the room buzzing with music played through the house system, plus loaner ink dabbers and large, colorful two-on cards that are easy to read. Winners take home real prizes, not plastic beer trinkets. All entrees are 31.9% off for dine in only. When the last song winds down and the wheel finishes its spin, the evening feels easy, fun, and full of good company.

Play That Funky Bingo turns music and memories into a lively game night, mixing familiar hits with good-natured rivalry. Each round highlights nostalgic themes like Decades, Motown, Classic Rock, and Love Songs, played at a comfortable volume that invites singalongs, table tapping, or a bit of air guitar. With more than 120 rotating rounds, the variety stays fresh, and every win sparks a room-wide Funky Bingo cheer. There is no cost to play and it is simple to pick up, making it an easy way to enjoy food, friends, and fun.

On the Milton Theatre mainstage, a fall production brings the famed musical thriller about the demon barber of Fleet Street to life. Set in nineteenth century London, the tale follows an unjustly exiled barber bent on revenge against the judge who framed him and harmed his young wife. He partners with Mrs. Lovett, the proprietor of a struggling pie shop beneath his new barbershop, and her fortunes rise as his deadly scheme unfolds. The intimate setting offers a close-up encounter with Stephen Sondheim's masterpiece. Winner of eight Tony Awards, including Best Musical, at its original Broadway premiere, the work has since become a worldwide success. Music and lyrics are by Stephen Sondheim, with a book by Hugh Wheeler from an adaptation by Christopher Bond. The original Broadway production was directed by Harold Prince, with orchestrations by Jonathan Tunick, and was produced by Richard Barr, Charles Woodward, Robert Fryer, Mary Lea Johnson, and Martin Richards, in association with Dean and Judy Manos. Presented through special arrangement with Music Theatre International, with authorized performance materials supplied by MTI.

A karaoke night where anyone can step into the spotlight. Sing favorite classics, channel a pop star persona, or cheer for friends between songs. The atmosphere stays upbeat and fun from start to finish.

See Sol at JD Shuckers. This recurring meet-up brings Sol to the venue on a regular basis.

Sing your heart out at Lefty’s during a relaxed karaoke night hosted by DJ Conrad. Take the mic and perform your favorite songs in a friendly setting where everyone can enjoy the spotlight. The event welcomes all ages, and admission is free.

Riverside Grill hosts a lively spin on bingo, presented by ICE Productions. Enjoy great music while you mark your cards and compete for prizes in every round. It is free to play and simple for first-timers as well as regulars. Bonus chances to win include 50/50 drawings, extra giveaways, and a monthly grand prize that can include a $100 Riverside Grill gift card.

A talk-and-performance program led by Daniel J. Bowen explores how music can strengthen communities. Daniel is a composer, arranger, pianist, and arts advocate from Maryland’s Eastern Shore whose collaborations include Grammy and Emmy recipients and Billboard-charting artists. His original work has been heard across major sports and entertainment outlets, including NBA and NHL coverage and networks such as TNT, ESPN, and Bravo. In 2017 he launched Symphony 21, a creative arts nonprofit that uplifts youth and brings people together through music. The event blends Daniel’s personal journey as an artist with big goals, a live musical set featuring a guest performer, and an inside look at how Symphony 21 is making a tangible difference, reflected in the growth and voices of those it serves. His background includes delivering a featured lecture during The Kennedy Center’s REACH Opening Festival, scoring PBS documentaries, and composing for the Stanley Cup Finals. The program invites reflection on what can happen when creativity and purpose work hand in hand.

Karaoke takes center stage at Chuck’s Backyard, presented by Coolbreeze Entertainment. Enjoy $4 Chuckie Dogs, happy hour deals, and $1 off crushes and house wine while the mic is open for your favorite songs.

A casual karaoke night where anyone can grab the mic and shine. Choose a beloved classic, unleash your pop star side, or cheer for friends from the crowd. The vibe is friendly and fun, with the spotlight open to all.