If you love live music, Sussex County is a great place to call home. On almost any night of the week, you can find something worth hearing—from free concerts at the Rehoboth Beach Bandstand and local restaurants featuring talented musicians to Broadway-style productions and nationally known performers.
A good place to begin is the Rehoboth Beach Bandstand. From Memorial Day weekend through Labor Day weekend, this popular seaside venue offers free nightly entertainment featuring everything from Elton John and Fleetwood Mac tribute bands to soul, pop, country, and beach music. The schedule also includes performances by renowned military ensembles such as the U.S. Army Field Band and the U.S. Navy Sea Chanters.
Concerts begin at 8 p.m. and typically last about 90 minutes, making them a perfect way to end a summer day at the beach.
The Milton Theatre keeps the music playing year-round with a blend of Broadway musicals, tribute bands, and local favorites. Productions such as Grease share the calendar with performances by well-known regional acts like Mama’s Black Sheep and Lower Case Blues at the theater’s Quayside outdoor stage.
Farther south, Freeman Arts Pavilion in Selbyville offers a similar mix, combining tribute acts and occasional Broadway productions with nationally recognized entertainers. This year’s lineup includes the Indigo Girls and James Taylor, although tickets for headline performers tend to disappear quickly.
Clear Space Theatre Company in Rehoboth Beach provides yet another musical destination. Its summer season features three popular productions—The Cher Show, Mean Girls, and Pretty Woman—while the theater’s Summer Cabaret Series offers an intimate evening of music and entertainment.
Of course, not every great performance happens in a theater.
Many local restaurants have made live music part of the dining experience. Bethany Blues, Bluecoast, Thompson Island Brewing Company, Conch Island, First State Brewing Company, Grain on the Rocks, Crooked Hammock Brewery, Mulligan’s Pointe, and Aqua regularly feature local musicians throughout the summer and beyond. Popular performers including Hot Sauce, Kerry Hallett, Girls Room, Mama’s Black Sheep, Nature and Nurture, and Lower Case Blues can often be found on their stages. Because schedules change frequently, it’s always a good idea to check directly with the venue or visit a band’s website before heading out.
One of Sussex County’s most unique music venues is The Listening Booth on Coastal Highway in Lewes. More than simply a place to hear live music, it describes itself as “a cultural experiment aimed at addressing one of the most insidious problems of our time: the loneliness epidemic.”
Home to the nonprofit organization “We’re Listening,” the venue uses original music, songwriting, and storytelling to foster connection and combat emotional isolation.
As its website explains, The Listening Booth is a place “where melodies become a shared experience, where lyrics act as a salve for collective solitude. ‘We’re Listening’ seeks to remind everyone that we’re part of something bigger, using the universal language of music to cut through the noise of modern disconnection.”
Visitors can enjoy live performances, songwriting workshops, open mic nights, and even poetry readings.
Outdoor concerts are another summertime tradition throughout Sussex County.
Nassau Valley Vineyards pairs live music with its Sunday afternoon Farmers’ Market, while Twin Branch Winery in Milton regularly welcomes performers such as Matt Lafferty.
Milton’s Wednesday Night Concert Series takes place at the gazebo along the Mispillion River behind the Milton Public Library. Lewes offers two popular weekly options: the Stango Park Concert Series on Tuesday evenings from 7 to 8:30 p.m. (with performances moving to Cape Henlopen High School in the event of rain) and Thursday evening concerts at Canalfront Park beginning at 6:30 p.m.
And then there’s Dewey Beach, where live music is practically a way of life. Venues such as Bottle & Cork, Rusty Rudder, Northbeach, Jimmy’s Grille, The Starboard, and Lighthouse Cove keep the music going well into the evening. The scene there tends to attract a younger crowd, but there’s no denying the energy.
Whether your tastes lean toward Broadway musicals, classic rock tributes, folk, blues, jazz, country, or original local artists, Sussex County offers an impressive soundtrack to everyday life. From intimate listening rooms and waterfront parks to bustling restaurants and large outdoor venues, there is no shortage of opportunities to discover your next favorite performance.
By Mary Jo Tarallo, Resident Journalist
Mary Jo Tarallo spent much of her career in public relations with various non-profits and spent 40 years involved with the ski industry as a journalist, public relations director for a national trade association and as executive director of the Learn to Ski and Snowboard initiative. Prior to her ski industry involvement she worked for the Maryland International Center in Baltimore and United Way of Central Maryland. She won a Gold Award for TV programming for a United Way simulcast that starred Oprah Winfrey. She has been cited for her work by numerous organizations. Mary Jo grew up in Baltimore, attended the University of Maryland and Towson University, lived in Washington, DC for 21 years and has been a full time resident of Rehoboth Beach and Milton since May 2019.
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