Live music in Milton, DE

Children and caregivers can enjoy a live class with Miss Maria featuring music and movement.

Kathy and Jimmy return to Harry’s for a rooftop set featuring classic songs alongside a few new tunes. The music ranges across country, rock and roll, oldies, and more.

Get into the Halloween spirit early with a celebration at Sussex Amvets Post 2. This rare gathering offers a one-of-a-kind experience that will not come around again for many months.

A lively karaoke session invites you to choose the tracks you love, step up to the microphone, and belt out your favorites. The setup is straightforward and focused on fun.

An encore performance of The McCartney Experience brings a faithful tribute to Sir Paul McCartney to Milton Theatre. Led by Jed Duvall with an accomplished band, the show covers Beatles classics, Wings favorites, and solo hits for a set filled with familiar tunes. The production has been praised by MTV founder Tom Freston and Al Cieslak of The Kirk McEwen Show for capturing Paul’s sound and stage presence. Ticket availability is limited.

Classical Cape May spotlights its own leadership in an intimate program at the Episcopal Church of the Advent in Cape May. Co-directors Robert Bullington and Brenda Leonard perform alongside pianist Noriko Schneiderman in an afternoon of chamber music and song. The lineup includes Prokofiev’s expressive Cello Sonata and Butterworth’s A Shropshire Lad, plus additional works for baritone, cello, and piano. With artist fees underwritten by Cape May MAC, admission is free for all, and donations are welcomed. The concert lasts about an hour and is followed by a reception where guests can meet the musicians.

Wind down the weekend at The Listening Booth with a relaxed, community jam where anyone can step in and play. This is not a standard open mic, it is a collaborative session that welcomes seasoned performers and newcomers who just want to enjoy live music. Instruments and basic gear are on hand so participants can focus on the vibe. A rotating host and a different guest bartender keep things fresh each week, making Sunday nights a lively spot to make music and connect.

Enjoy a high-energy twist on bingo that swaps numbered calls for hit songs. Themed rounds pull from Motown, 60s favorites, 90s rock, pop and more, offering a wide mix across decades and genres. Paper cards and real dabbers keep it classic while the room sparks with spontaneous singing, table drumming and the occasional conga line. Each time someone scores bingo, their name goes on a winners list, then names are drawn later to award nightly prizes, including gift cards to Coastal Taproom and Henlopen Pizza Kitchen.

Enjoy a lively twist on bingo with a music-filled game for all ages. Listen for popular songs, find them on your bingo card, and sing or dance along if you like. The game features themed rounds, fun twists, weekly prizes, and plenty of laughs. It is free to play.

Spend time with Sol at The Crab Barn in Millsboro.

Enjoy a lively bingo game set to music, with rounds spanning many eras and genres, prizes to win, and plenty of unexpected moments. Play for free with full-color paper cards and ink dabbers provided.

Uke players and acoustic friends can learn, play, sing, and strum together.

Enjoy a free, all-ages evening of music-themed games at Lefty’s Alley & Eats, hosted by Jersey John. Try Name That Tune, trivia, and Jersey Feud, with friendly competition, laughter, food, drinks, and prizes.

Hosted by Nate McCormick, this open mic welcomes performers of all kinds for an acoustic evening with no drums or amps. Original music is encouraged, and covers are welcome. The venue has a full sound system, an upright piano, and house guitars available to borrow. Each week features a songwriting prompt, and performers who write a song inspired by the prompt and play it the following week receive a free drink. There is no cover charge, with a two-drink minimum.

Enjoy a free-to-play game of Music Bingo featuring nostalgic themes such as decades, Motown, classic rock, and love songs. With more than 120 rotating rounds, the game offers fresh selections each week and plenty of chances to sing along, tap to the beat, and enjoy food, friends, and friendly competition.

Enjoy a matinee celebration of Elvis Presley’s music as Jesse Garron delivers a polished tribute filled with the voice, look, and charisma that made the original artist a legend. Backed by live musicians and female vocalists, the show spans rock, pop, gospel, and oldies that resonate across three generations. Garron has performed this tribute since 1997 and presents it with respect, using the name of Elvis’s twin brother who passed at birth to honor the legacy while recognizing there was only one Elvis. His passion began in early childhood and led to a standout high school performance at 17, which opened doors to larger stages and eventually to venues across the country, often playing to full houses. His journey includes an invitation to perform for the US Embassy in Algiers and recognition from legendary Elvis guitarist James Burton after a show in Louisiana. Audiences who saw Elvis live, along with people connected to the Presley family, frequently praise the authenticity of his portrayal. The production has drawn widespread media attention through billboards, radio, television, and feature articles, and in 2019 he was inducted into the International Elvis Tribute Artist Hall of Fame for his dedication to preserving the King’s legacy.

Enjoy half-price pasta all evening at Dalmata, along with musical bingo hosted by James. Test your music knowledge, sing along to favorite songs, compete with friends, and win prizes.

Spend a Thursday evening with Sol at JD Shuckers in Lewes.

Enjoy a relaxed karaoke gathering at Lefty’s, where singers of all ages can take the microphone and perform their favorite tunes with DJ Conrad. There is no cover charge.

Jesse Garron presents a tribute to Elvis, honoring the singer and his legacy. Performing since 1997, Garron is known for his vocal range, appearance, and charismatic portrayal. Backed by live musicians and female vocalists, he performs rock, pop, gospel, and oldies songs spanning three generations. In 2019, Garron was inducted into the International Elvis Tribute Artist Hall of Fame.

Take a turn in the spotlight with karaoke, sing a classic or a pop favorite, or cheer on friends as they perform.