Summer may be winding down, but there are still plenty of ways to enjoy the season across Coastal Delaware. 

From outdoor concerts and beach parties to community events, family activities, local fundraisers, and sunset cruises, the second half of August is filled with things to do before fall arrives.

Believe In Tomorrow Beach 5K at Big Chill Beach Club

This one is much more than your typical 5K. 

You can run or walk across the Indian River Inlet Bridge while taking in sunset views, then head back to Big Chill Beach Club for a post-race party with food, games, raffles, awards, and more. 

Participants receive a race shirt and bib, and families can bring children ages 3 and under along in strollers without registering them separately. 

If you can’t join the race in person, there’s also a virtual option that still lets you participate and receive a race shirt afterward. 

Dogs cannot join the course because the race takes place within the state park. 

Best of all, the event supports Believe In Tomorrow Children’s Foundation, with proceeds benefiting critically ill children and their families through the organization’s beach respite program.

• Date: Thursday, August 20th
• Time: 6pm
• Location: 27099 Coastal Highway, Bethany Beach

Jackson Family Wine Dinner at Harvest Tide Steakhouse

Turn dinner into a full tasting experience with a four-course seasonal menu paired with selections from Jackson Family Wines. 

The evening is built around fresh summer flavors, with seafood, dry-aged steak, wine pairings, and a seasonal dessert all coming together across courses named Golden Coast, Pacific Orchard, Sonoma Ember, and Lemon Grove. 

If you’ve been looking for an excuse to make dinner out feel a little more special, this is definitely one to consider.

• Date: Thursday, August 20th
• Time: 6:30pm
• Location: 410 E Savannah Road, Lewes

Image: Rocking the Docks

Rocking The Docks Presents Pink Talking Fish at Lewes Ferry Grounds

Pink Floyd, Talking Heads, and Phish may sound like three very different bands, but Pink Talking Fish has built an entire live show around finding the connections between them. 

Instead of simply playing tribute songs one after another, the group blends the emotion and atmosphere of Pink Floyd with the funky, danceable sound of Talking Heads and the constantly changing styles and compositions of Phish. 

The result is a show designed for people who already love these bands but want to hear their music presented in a completely different way.

And Rocking The Docks adds plenty to the experience beyond the performance itself. 

You can grab something from the food trucks, order craft beer, wine, or cocktails, and enjoy panoramic views of the bay and sunset while listening to the show. 

Free on-site parking is available, blankets and low-back chairs are welcome in designated seated areas, and the ferry grounds are handicap accessible.

• Date: Thursday, August 20th
• Time: 6pm
• Location: 43 Cape Henlopen Drive, Lewes

Community Block Party at Salem Church

Bring a chair, find a spot on the lawn, and spend the evening enjoying a free community gathering with food, music, games, bounce houses, face painting, and plenty of other family-friendly activities. 

You’ll also have the chance to meet and connect with a variety of community groups that come out to participate in the event.

• Date: Friday, August 21st
• Hours: 6pm to 8pm
• Location: 29 W Church Street, Selbyville

Shanty Night at the Sussex Tavern

If you’re willing to do a little singing, cheering, ranting, and raving, Shanty Night turns a regular night at the Sussex Tavern into something that feels a little more like stepping onto a ship full of British sailors. 

The monthly event is all about traditional shanties, audience participation, and having fun with the whole theme. It’s free to join in, with drinks available separately.

• Date: Friday, August 21st
• Hours: 6pm to 8pm
• Location: 110 Shipcarpenter Street, Lewes

Beach BBQ at Children's Beach House

Kick off your shoes and spend an evening right along Lewes Bay during the Beach BBQ at Children’s Beach House. 

You can enjoy live music, food, beer, wine, and signature cocktails while hanging out across the beach and waterfront decks, then hit the dance floor or see what catches your eye during the live auction. 

It’s a full summer night by the water, but it also supports the work Children’s Beach House does in the community.

• Date: Saturday, August 22nd
• Hours: 6:30pm to 9:30pm
• Location: 1800 Bay Avenue, Lewes

PAWS for Reading at South Coastal Public Library

For kids who could use a little extra confidence reading aloud, PAWS for Reading gives them a pretty forgiving audience: dogs. 

Trained dogs and their owners sit with children ages 5 and up for individual 10-minute reading sessions, creating a more relaxed and supportive environment to practice. 

Kids can bring a favorite book from home or choose something from the library, but you’ll need to call ahead to register.

• Date: Tuesday, August 25th
• Hours: 4pm to 5pm
• Location: 43 Kent Avenue, Bethany Beach

Rocking The Docks Presents Ripe at Lewes Ferry Grounds

Ripe’s story started with the band making songs together in a basement underneath a Subway and selling tickets by hand outside a coffee shop, and that sense of friendship and collaboration has stayed at the center of the group ever since. 

Their music has grown alongside them, with newer material exploring nostalgia, change, connection, and what happens when a group of longtime friends keeps pushing creatively together. 

If you like energetic live bands that clearly feed off each other onstage, this is one to put on your list.

You’ll also get the full Rocking The Docks experience, with food trucks, craft beer, wine, cocktails, and wide-open views of the bay and sunset surrounding the stage. 

You can bring a blanket or low-back chair for the designated seated areas, parking is available on site, and the grounds are handicap accessible.

• Date: Thursday, August 27th
• Time: 6pm 
• Location: 43 Cape Henlopen Drive, Lewes

Image: Decade80

Full Moon Party x Decade 80 at Big Chill Beach Club

If your ideal summer night includes '80s music, dancing, and a full moon over the beach, Big Chill is putting all three together. 

Decade 80 Band will take over the Sunset Lounge with live versions of some of the decade’s biggest songs, so you can expect plenty of music you already know well enough to sing along with.

At the same time, the sand pit turns into a Silent Disco where you can grab a pair of headphones and switch between two different channels of dance music. 

You can bounce between the live band and the disco throughout the night depending on what you feel like listening to, all with the beach and full moon as the backdrop.

• Date: Thursday, August 27th
• Hours: 6pm to 9pm
• Location: 27099 Coastal Highway, Bethany Beach

Riding for Freedom at the Southern Delaware Therapeutic Riding

Riding for Freedom combines a celebration of America’s 250th anniversary with a night dedicated to supporting Southern Delaware Therapeutic Riding. 

Tony Sciuto and Robbie LaBlanc will take the stage with a live set of Beatles favorites while J&B Grilling serves up food for the evening. 

You’ll also have an open bar with beer, wine, and canned spirits to enjoy while you listen.

There’s also a live auction filled with experiences put together with the help of local businesses and restaurants, giving you another way to support the organization while potentially taking something special home. 

Every dollar raised goes directly toward the participants and horses at Southern Delaware Therapeutic Riding, making the entire evening a fundraiser for the programs they provide.

• Date: Thursday, August 27th
• Hours: 6pm to 9pm
• Location: 17170 Harbeson Road, Milton

Emo Night at The Millville Boardwalk

Yes, you can bring the kids to Emo Night. The Millville Boardwalk is putting a family-friendly spin on the theme, so you can enjoy the music without giving up all the other things there are to do around the complex. 

Between songs, you can grab something from Agape Creamery, play at Captain’s Quarters Arcade, try Lighthouse Beach Golf, ride the go-karts, or spend some time around the stage and pavilion area.

• Date: Friday, August 28th
• Time: 8pm
• Location: 35287 Atlantic Avenue, Millville

Magical Mystery Doors Presents: Beatles/Zeppelin/Doors at Freeman Arts Pavilion

If you love The Beatles, Led Zeppelin, or The Doors, Magical Mystery Doors gives you a tribute show that goes much further than simply covering their biggest songs. 

The act actually blends music from all three bands together, creating arrangements you wouldn’t hear anywhere else. 

The melody of The Doors’ “Hello, I Love You,” for example, can meet Led Zeppelin’s “Misty Mountain Hop,” while the beat of “When the Levee Breaks” can be paired with The Beatles’ “Dear Prudence.” 

Other sequences move between songs from all three catalogs in ways designed to make familiar music feel completely different.

The visual side is a big part of the show too, with video screens and lighting helping turn the performance into a more immersive experience rather than a straightforward tribute concert. 

You’ll still hear plenty of the songs you already know, but the fun is seeing how the band rearranges and connects them. 

• Date: Friday, August 28th
• Time: 7:30pm
• Location: 31806 Lakeview Drive, Selbyville

Neighborhood Block Party with WHYY at Lewes Public Library

The Lewes Public Library and WHYY Public Media are turning the library’s backyard pavilion into an end-of-summer neighborhood party with plenty for families to do. 

You can check out community vehicles, play games, join activities, listen to music, win prizes, cool off with popsicles from Frios Gourmet Pops, and take a train tour with the Lewes Junction Railroad & Bridge Association.

There will also be a special interactive appearance from Albie of Albie’s Elevator, giving younger visitors another reason to come out. 

The whole event is free, open to all ages, and doesn’t require registration. 

And if rain gets in the way of an outdoor block party, everything simply moves inside the library.

• Date: Saturday, August 29th
• Hours: 11am to 1pm
• Location: 111 Adams Avenue, Lewes

Don’t Tell Comedy in Rehoboth Beach 

Don’t Tell Comedy makes the mystery part of the show. 

When you buy a ticket, you know the general area but not the exact indoor venue, with that information revealed to ticket holders on the morning of the performance. 

You won’t know who the comedians are either. Instead, a surprise lineup of four to seven comics takes the stage, potentially mixing emerging local performers with nationally touring talent and the occasional familiar face.

The show itself runs around 70 to 90 minutes and is for ages 21 and up. 

Chairs are provided, drinks are available for purchase, outside snacks are allowed, and the venue is wheelchair accessible. 

There’s also no traditional two-drink minimum, so the focus stays on showing up, finding out where the secret venue is, and discovering who’s performing when they actually walk onstage.

• Date: Saturday, August 29th
• Time: 9pm
• Location: Community Space in Rehoboth Beach

Beginnings: A Celebration of the Music of Chicago at Milton Theatre

If Chicago is one of those bands you never get tired of hearing, Beginnings has spent more than two decades recreating that sound onstage.

The New York City-based tribute band formed in 2002 and performs in Chicago’s original classic-era seven-piece configuration, putting a big emphasis on reproducing the arrangements, musicianship, and intensity of the original group.

Rather than simply playing recognizable hits, Beginnings builds its performances around the full Chicago concert experience and the extensive catalog the band has created over the years. 

It’s one for longtime fans who want to hear those songs played live with the horns, harmonies, and musical detail that made them so distinctive in the first place.

• Date: Sunday, August 30th
• Hours: 3pm & 7:30pm
• Location: 110 Union Street, Milton

Sunset Cruise on the Sand Dollar

Finish off summer from the water aboard the Sand Dollar, a 45-foot pontoon powerboat designed with open views and a partially covered area. 

The family-friendly cruise takes you around Rehoboth Bay, where you can get a closer look at waterfront homes, natural scenery, and local wildlife while enjoying some time out on the bay.

• Date: Monday, August 31st
• Time: 6:30pm
• Location: 113 Dickinson Avenue, Dewey Beach

Keep following the blog for more events, activities, and ways to enjoy the final weeks of summer in Coastal Delaware.

Have any questions about our blog(s), the Coastal Delaware real estate market, or local life in our beautiful beach towns? Do you think there is something we should write about? Did you see an event coming up that we should know about? Shoot us an email at [email protected] or give us a call at (302) 212-0074. We would love to hear from you!