Labor Day Weekend Live Music in Dewey Beach 2026

Summer’s last stand in Dewey Beach is always a good one, and this Labor Day weekend is stacked. Here’s your guide to who’s playing where, from Friday through Monday.

Bottle & Cork

Bottle & Cork, 1807 Highway One

The Cork is going big this weekend with a ticketed Friday headliner and free jam sessions Saturday and Sunday.

Friday, Sept 4: Saved By The 90s takes over at 8 PM. 21+ show.

Saturday, Sept 5: The Saturday Jam Session kicks off at 3 PM with Gab Cinque, Turning the Tide, Love Seed Mama Jump, and Knappy. This one’s free and it runs all afternoon.

Sunday, Sept 6: Jam Session at 5 PM featuring Gab Cinque, Stealing Savanah, Benderz, Garden State Radio, and Knappy.

Don’t Miss: Love Seed Mama Jump at the Saturday session. They’ve been a Dewey institution for 35 years and the Cork jam format lets them stretch out.

Rusty Rudder

Rusty Rudder, 113 Dickinson Street

The Rudder runs live music from afternoon to late night all four days of the weekend. Three acts a day Friday through Sunday, two on Monday.

Friday, Sept 4: Keith Mack Duo (3 PM), Flat Moon Society (6 PM), Stealing Savanah (9 PM)

Saturday, Sept 5: Brian & Bacon (2 PM), Jenni+1 (5 PM), 3AM Tokyo (9 PM)

Sunday, Sept 6: John & Marc (2 PM), Chris & Dave (5:30 PM), Love Seed Mama Jump (9 PM)

Monday, Sept 7 (Labor Day): Kono Nation Duo (1 PM), Fantastic Four (4 PM)

Insider Tip: The Rudder is the only venue with confirmed Monday programming, so if you’re staying through Labor Day itself, this is your spot.

The Starboard

The Starboard, 2009 Highway One

The Starboard is running extended Labor Day hours from Thursday through Monday, 8 AM to 1 AM. Check their social media for the full event calendar.

The Double Feature

Here’s a fun one for music fans: Love Seed Mama Jump plays Bottle & Cork’s Saturday jam (3 PM) and then headlines at Rusty Rudder on Sunday night (9 PM). Stealing Savanah pulls the same trick, playing the Rudder Friday at 9 PM and the Cork’s Sunday jam at 5 PM. Plan accordingly.

Schedules can change. Confirm times with the venue before heading out.

Updated September 4, 2026