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Best of September: 15+ Delaware Beach Events for This Month 

August 28, 2021

Lauren Cosca


Check out more Delaware Beach Area Events on our full Calendar!

The award-winning Southern Delaware Food, Wine & Music Fest takes place Sat Sept 18th! 


The summer isn’t over yet at the Delaware beaches! The month of September features an amazing lineup of fun activities and events for people of all ages, like the Bethany Beach Boardwalk Art Festival, the Dewey Beach Sprint Triathlon, and more! Keep reading below to see other cool events scheduled to finish out an awesome summer season at the beach!

1.    What: The Skivvies with Randy Harrison and Diana Huey
When: Friday, September 3 | 7:30 p.m.
Where: Rehoboth Beach Convention Center | 229 Rehoboth Ave, Rehoboth Beach, DE
Music is a key part of CAMP Rehoboth’s Labor Day activities and this summer is no different. The first Friday of September will feature the return of the Skivvies, Lauren Molina and Nick Cearley, performing stripped-down arrangements of eclectic covers and eccentric originals. The Skivvies will perform with special guests: Randy Harrison (Justin Taylor from Queer as Folk) and Diana Huey (who played Ariel in the national tour of Disney’s The Little Mermaid and Kim in Miss Saigon).


2.    What: 5th Annual Beach Goes Red, White & Blue
When: Saturday, September 4| All Day
Where: Rehoboth Beach Bandstand
The Rehoboth Beach-Dewey Beach Chamber of Commerce is hosting this awesome event to salute and honor police officers, firefighters, paramedics, the military, medical frontline workers, and ALL those who serve. Enjoy entertainment from the Rehoboth Beach Bandstand, family fun adventures, breathtaking displays and more! Patrons of all ages can enjoy the many activities planned such as the Kid’s “Boot Camp” with Drill Instructor Gordon and a musical performance by Frank Nanna and Group.


3.    What: Annual Outdoor Antiques & Vintage Fair - Lewes Historical Society
When: Saturday, September 4| 9 a.m. to 3 p.m.
Where: 110 Shipcarpenter Street, Lewes, DE 19958
Surround yourself with antique treasures, unique vintage-ware items, and one-of-a-kind art forms from all periods. Antiques, vintage dealers, and artisans will participate in the show and feature antiques along with eclectic treasures and art. Food vendors will provide a variety of options available for purchase, and music will add to the festive atmosphere. The historic LHS Shipcarpenter Street Campus will come to life as well as the Society's Cannonball House Maritime Museum, where visitors can learn about the hardships and lives of sailors ashore and afloat through demonstrations of traditional maritime trades, and the Lewes History Museum.


4.    What: Dewey Beach 90’s Powerpop Reunion at Bottle & Cork
When: Friday, September 10| 7:30 to 11:45 p.m.
This multi-act festival features appearances from some of the region's most beloved bands from the 90's, many of whom are reuniting just for this show on September 10th! Don't miss the special late-night jam featuring reunion mini-sets from Tisra Til / Mystery Machine (led by Cliff Hillis) and the band that was the precursor to the Caulfields - Beat Clinic (featuring guitarist Chris Ryan)! Tickets are $10 and the event is 21+. 


5.    What: 43rd Annual Nanticoke Indian Powwow
When: Friday, September 10 to Sunday, September 12| All Day
Where: 30045 Eagle Crest Rd, Milton, DE
The 43rd Annual Nanticoke Indian Powwow will kick off with a pig roast for all participating vendors on Friday from 4 to 8 p.m. There will be two dance sessions starting promptly at 12 p.m. On Sunday, Powwow hours will be 10 a.m. to 7 p.m.; with a church service being held from 8:30 to 10 a.m. There will be one dance session following the church service. This event is $5.00 for children aged 11 to 17, and $8.00 for adults. The Powwow will feature food, native jewelry and apparel vendors. 


6.    What: Bethany Beach Boardwalk Art Festival
When: Saturday, September 11| 20 a.m. to 5 p.m.
Where: Bethany Beach Boardwalk
The 43rd Annual Bethany Beach Boardwalk Arts Festival in downtown Bethany Beach is here! This year’s event includes fine artists featuring paintings, wood work, metal, clay, baskets, jewelry, porcelain, and more! Support your local arts community this year when you attend the festival. Parking is available in downtown Bethany Beach. 


7.    What: Rehoboth Beach Bear Weekend
When: Wednesday, September 16 to Sunday, September 19
Where: Atlantic Sands Hotel & Conference Center | 1 Baltimore Ave, Rehoboth Beach, DE
The Rehoboth Beach Bear Weekend is back! The Atlantic Sands is the host hotel, and reservations must be made through them. This event is the flagship fundraiser to help their mission to promote camaraderie and inclusiveness and to help LGBTQIA+ students in local area high schools achieve their education and career goals with financial scholarships. The weekend includes a welcome dinner, an early Halloween party, a comedy set from Eric Hahn, and more! 


8.    What: Blade Rehoboth Summer Closing Party Featuring Pamala Stanley
When: Friday, September 17 | 6 to 8 p.m.
Where: The Pines | 56 Baltimore Ave, Rehoboth Beach, DE
Join the Washington Blade for their Rehoboth Summer Closing Party at The Pines featuring a special performance by Pamala Stanley! Tickets are $20.00 and include drink tickets and light appetizers. Money raised supports the Steve Elkins Memorial Fellowship, an organization created to honor the co-founder of the CAMP Rehoboth LGBT community center. 


9.    What: Dewey Beach Sprint Triathlon
When: Saturday, September 18 | 8 a.m. to 11 p.m.
Where: Delaware Seashore State Park | 25039 Coastal Hwy, Rehoboth Beach, DE
This event features a 1/2-mile ocean swim, 15-mile bike and 3.5-mile run. There is also the option to form a relay team with two other participants. The Aquabike division is another choice for participants which includes a 1/2-mile swim and a 15-mile bike It’s a no frills, grass roots community event and a Dewey Beach tradition that brings athletes and their families from near and far to the resort area. 


10.    What: 6th Annual Southern Delaware Wine, Food, and Music Festival
When: Saturday, September 18 | 4 to 7:30 p.m.
Where: 23767 Samuel Adams Cir, Millsboro, DE
This event started as a way to feature the very best tastes, sounds, people, and passions of coastal southern Delaware. Six years later, SoDEL Fest is widely known for unique culinary experiences, award-winning chefs, and winemakers from around the world. But it's so much more than an amazingly indulgent day of wine, food, & music. It's a celebration of life, laughter, friendship, and togetherness that pours each year's proceeds into local non-profits doing important work to strengthen the southern Delaware community. This year it is $125.00 to enter the festival. 


11.    What: Chix with Stix
When: Wednesday, September 22 | 2 to 3 p.m.
Where: South Costal Library | 43 Kent Ave, Bethany Beach, DE
The Chix with Stix meetings are officially back on! The group will meet quarterly to discuss crocheting, knitting and needleworking. All skill levels are welcome to attend. This meeting will take place in the library reading garden with social distancing. Registration is required. 


12.    What: Kip Moore at Bottle & Cork
When: Thursday, September 23 | 8 to 11 p.m.
Where: Bottle & Cork | 1807 HIGHWAY ONE DEWEY BEACH, DE 19971
You must be over the age of 21 to attend this rockin’ concert with Kip at Bottle & Cork! Grab a ticket for only $69 and jam out to some of his classics including “Somethin’ ‘Bout a Truck.” This concert is the perfect way to end the summer on a high note and you won’t want to miss out. 


13.    What: The FIREFLY Festival 
When: Thursday, September 23 to Sunday, September 26| All Day
Where: The Woodlands|Dover, DE
Headbang it out this summer with one of the greatest lineups to ever grace the stage! Sing along to hits from Billie Eilish, Cage the Elephant, The Killers, Wiz Khalifa, Tame Impala, Lizzo, Machine Gun Kelly, Nelly, Blackbear, Megan Thee Stallion, Diplo, Girl in Red, Band of Horses, Dominic Fike, Lovely The Band, Phoebe Bridgers, and Roddy Rich. Tickets are $119.00 plus fees for one day general admission. Visit the website for information on shuttles, parking, and camping. 


14.    What: Dewey / Rehoboth Bacon Fest 7.5
When: Friday, September 24 to Sunday, September 26 
Where: Dewey Beach, DE
Enjoy a weekend at the beach with some amazing bacon creations. Saturday features bacon samples in Dewey Beach, while on Sunday the samples can be found in Rehoboth. VIP passes can be picked up Friday evening. The process is fun and easy. Pick up your starting information at any of the welcome events, arrive to your start location on Saturday, follow the map around enjoying bacon creations, and repeat on Sunday! Experience samples of hot, steamy, sizzling bacon from over 22 locations!


15.    What: Oktoberfest presented by Canalside Inn and Rehoboth Beach Main Street
When: Saturday, September 25 | 2 to 7 p.m.
Where: Rehoboth Beach Convention Center | 229 Rehoboth Ave, Rehoboth Beach, DE
Join Canalside Inn to create a new Rehoboth Beach annual tradition. Come celebrate Oktoberfest with local craft breweries, food vendors, artists, and your favorite Rehoboth Beach merchants. Music and beach vibes are included! This family friendly event is open to everyone featuring banquet style dining tables. Enjoy traditional German cuisine such as Bratwurst, Jaeger schnitzel, and Sauerkraut and indulge in the best German Oktoberfest beers like Dunkel, Pilsner, and Hefeweizen in the Biergarten. 


Check out more Delaware Beach Area Events on our Calendar!

For more things to See & Do at the Delaware Beaches! Visit our See & Do section!


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