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Events This Weekend in Delaware and Maryland

September 28, 2023

After pretty much a complete washout of last weekend's outdoor events, we try again this week as another round of popular fall festivals can be found on the events calendar for this final weekend of September.

Headlined by big events in Milford, Ocean City, Dewey Beach, and Lewes, this weekend again features some of the best festivals of the fall at and near the Delaware and Maryland beaches.

It's a great chance to pick your favorite and enjoy the great outdoors one final time before the weather turns cooler and we all begin staying indoors more and more until next spring.

With that said, here are the Oldfather Group's top choices for family-friendly fall festivals during the weekend of September 29-October 1.

Make it a great weekend everyone!

Ladybug Music Festival (September 30)

This annual music festival in downtown Milford features a huge selection of female artists and is scheduled for 4 to 9 p.m. on Saturday, September 30.

This free festival features a total of seven stages located throughout town, with the main stage nestled in the closed-off section of downtown on Walnut Street.

Food trucks will be on-site for the event, so come hungry and enjoy some great local food while listening to a nice selection of fantastic female-led music.

In the case of rain, the festival will instead be moved to Sunday, October 1.

For a full lineup of scheduled artists, as well as much more information on the 2023 Ladybug Music Festival, visit theladybugfestival.com.

Dewey Golden Jubilee (September 29-30)

Approximately 150 Golden Retrievers and their owners are expected this weekend for the second of two annual “Golden” weekends in Dewey Beach.

Frequently cited as one of the most dog-friendly beaches in America, Dewey Beach will again be party central this weekend, with scheduled activities to include a parade through Rehoboth Beach on Friday night, a romp on the beach on Saturday, a bonfire on the beach on Saturday night, and much more.

For more information on the Autumn Golden Jubilee event, visit deweysgoldenjubilee.com.

Oceans Calling Music Festival (September 29-October 1)

This three-day music festival takes place on three separate stages on the Ocean City Boardwalk, taking place from Friday, September 29, through Sunday, October 1.

Headliners for 2023 include Jack Johnson, Alanis Morissette, John Mayer, Third Eye Blind, Sheryl Crow, Weezer, and others.

To learn more about the 2023 Oceans Calling Music Festival, or to order tickets, visit oceanscallingfestival.com.

Click here for the rest of this weekend’s busy events calendar

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