Live music in Milton, DE

The AnnaRagz duo brings live music to Twin Branch Winery, featuring Delmarva vocalist Anna Burgess-Woodard and saxophonist John Ragonese. Their duo performance offers a mix of familiar favorites and classic songs.

Look for Sol at JD Shuckers inside the Peddler's Village Shopping Center.

Lefty’s hosts Karaoke Thursdays each week with DJ Conrad at the helm. Expect a relaxed, welcoming vibe where anyone can take the mic, sing favorite tunes, and enjoy a moment in the spotlight. All ages are welcome, and there is no admission fee, making it an easy outing for friends and families.

Mingo brings a lively twist to classic bingo at Riverside Grill, hosted by ICE Productions. Players mark their cards to music and compete for prizes in every round. Extra chances to win include 50/50 drawings and a monthly shot at a $100 Riverside Grill gift card. It is free to play, easy to learn, and welcoming for first-timers and regulars, with music, giveaways, and an upbeat atmosphere throughout.

Experience dynamic jazz with a soulful R&B tilt as The Lao Tizer Band returns to The Room @ Cedar Grove after a sold-out 2025 debut. The group, a Jazz Group of the Year nominee, performs in celebration of AMPLIFY, a new album and video release that marks a significant step forward with five brand-new vocal tracks and four original instrumentals. Captured live at EastWest Studios in Hollywood with a seven-camera shoot and a cast of notable players, the project showcases the band’s elevated sound and energy. On stage, keyboardist and bandleader Lao Tizer, a former Best New Jazz Artist nominee, is joined by platinum-selling American Idol vocalist Elliott Yamin, GRAMMY-winning drummer Gene Coye, and bassist Anthony Crawford, a 2022 Rolling Stone Bassist of the Year nominee known for work with Erykah Badu and Jeff Lorber. Tickets are $95 and include dinner and the music, with beverages available for purchase separately. Gratuity is not included, and tickets are non-refundable.

Enjoy a weekly karaoke night where anyone can step into the spotlight. Choose a beloved classic, try a pop hit, or cheer on friends from the audience. Reservations are requested.

Charlie & the CoolTones are appearing at Dockside Marina Bar + Grill at Indian River Inlet. Please note that the event date has changed.

The Kagan Nuss Duo returns to Surf N Turf in Milford for a high-energy night featuring favorites by Billy Joel, Elton John, Ray Charles, and more.

Sweet Leda takes the stage at The Room at Cedar Grove, led by Julie Cymek’s soulful voice and magnetic presence. The band delivers a vibrant mix of modern funk, psychedelic rock, soul, and pop, with original songs that nod to Led Zeppelin and Red Hot Chili Peppers. Industry veteran Lou Plaia has praised them as a highlight at the festivals they play. Admission is $64 and includes dinner and the concert, with beverages sold separately. Gratuity is not included, and all ticket purchases are final.

Step up to the mic, pick the songs you love, and sing your heart out. This karaoke gathering keeps it simple so the focus stays on the music and the fun. Bring your best vocals or your loudest cheers, and enjoy a lighthearted night of singing.

Backlash Fest 2026 brings a full day of live performances and community fun, presented by Bottle & Cork in Dewey Beach. The lineup features The British Invasion Years, A ’60s Musical Revolution, with special guests HeadHigh, Rogue Agents, and Clayton Eberly, and Mikey G as host. Attendees can enjoy music alongside local vendors, food, games, and a welcoming festival atmosphere in support of a good cause. Guests are encouraged to bring chairs and share the experience with friends. Event partners include J&A Electrical Services, Shore Water Refining, Long Neck Dispensary, Betterliving of Delmarva, George Hoffman Heating & Air Conditioning, AC Dreamscapes, J and C Home Exteriors, and Christina’s Cuts by the Coast. For those planning an overnight stay, Avid hotel Millsboro offers accommodations with a discounted room rate for Backlash 2026.

After a high-energy ten-week run, the competition reaches its grand sing-off finale as the ten winners from earlier rounds return to battle for the top spot. Expect soaring vocals, standout stagecraft, and the kind of head-to-head excitement only a true karaoke showdown can deliver. One performer will be crowned champion and receive a five-night stay in 2027. The night promises wall-to-wall performances that keep the room singing, clapping, and dancing, celebrating community, talent, and the shared joy of music as the final note decides it all.

Classic rock favorites from the 1960s through the 1990s take center stage, with a hint of country in the mix. The group features Robin Rohr on lead vocals and bass guitar, Chuck Cinaglia on vocals and lead guitar, and Paul Galonsky on drums.

Kagan Nuss and Johnny Rags, performing as The Great Chasers, present a piano and saxophone set at Arena's Restaurant (Deli Downtown Rehoboth). The program features music by Billy Joel, Ray Charles, and Elton John, plus upbeat favorites from the 1950s. Sandwiches and beverages are available from the restaurant.

The Jimmies 80s Flashback Band turns Bethany Blues into an 80s time capsule with a high-energy set packed with the era’s signature hooks and anthems. Covering New Wave, pop, rock, punk, and hair metal, the performance delivers a lively soundtrack with plenty of sing-along moments.

DJ Malachi takes the decks for a night filled with hits. The series continues every Saturday throughout the summer with weekly DJ sets. There is no cover charge.

Freddie's Follies hosts a lively drag showcase featuring a talented roster of queens delivering high-energy performances that keep the audience engaged. It highlights personality, originality, boldness, and skill throughout the show. There is a $5 cover at the door, and table reservations are available.

Answer the call for karaoke. Pick the songs you love, step up to the microphone, and give it everything you have. It is easy to jump in and the emphasis is on having fun. Make sure not to miss it.

Acoustic Night at Aqua features live music from Kerry Hallett, setting the tone for Monday with an acoustic soundtrack.

At Lefty’s, try a musical twist on bingo where hit songs replace numbers. Listen, recognize the tracks, and mark them on your card, then sing or dance along if you want. The event features themed rounds with lively music, playful surprises, and weekly prizes, keeping the laughs coming. There is no cost to participate, and players of every age are welcome.

Step into the spotlight for karaoke. Sing beloved classics, tap into a pop star vibe, or cheer on friends from the crowd.

Sol appears at The Crab Barn on Tuesdays. This is a recurring gathering featuring Sol at the venue.

Step into the spotlight at a karaoke night where anyone can grab the mic. Sing timeless favorites, tap into your pop-star side, or cheer on friends from the crowd. It is all about sharing the stage and having fun together.

At Lewes Senior Activity Center, ukulele players and other acoustic enthusiasts come together to learn, play, sing, and strum.

Hosted by Nate McCormick, The Listening Booth offers a weekly acoustic open mic that welcomes everyone. Performances are acoustic only with no drums or amplifiers, and while original music is encouraged, covers are welcome. There is no cover charge, and the venue has a two drink minimum. A full sound system, an upright piano, and house guitars are available for participants. Each week features a songwriting prompt, and anyone who writes a song from that prompt and performs it the following week earns a free drink. No tickets or RSVP are required.

Surf & Turf Bar & Grill hosts a lively music bingo experience that blends favorite tunes with the classic thrill of marking your card. Rounds draw on nostalgic themes such as decades, Motown, classic rock, and love songs, with the volume set for easy singalongs, table tapping, or a little air guitar. With a library of more than 120 rotating rounds, the mix stays fresh, and when someone wins, the room erupts with a cheerful shout of “Funky Bingo!” It is free to play and simple to pick up, offering a relaxed way to enjoy food, friends, and lighthearted competition.

Step into the spotlight at a karaoke night where anyone can sing. Pick a favorite classic, channel an inner pop star, or cheer on friends as they perform. The setting welcomes confident vocalists and first-timers alike, offering a relaxed way to share songs and enjoy supportive applause.