Looking for the best things to do in Coastal Delaware during the first fall weekend? From Friday, September 5th through Sunday, September 7th, the beaches and towns are buzzing with live music, food and drink events, art festivals, outdoor adventures, and more! 

From Rehoboth and Lewes to Bethany Beach, here’s your guide to the top activities and events happening this weekend:

Friday, September 5th

Rock the Boat 2025 with Cape May-Lewes Ferry

Kick off your weekend on the water with Rock the Boat, a lively cruise featuring Delaware’s favorite rock-and-roll party band, Glass Onion. 

Guests can enjoy great music, dancing, and bar service while taking in the stunning views of the Delaware Bay. 

The atmosphere is festive, making it an experience that combines live entertainment and a scenic ferry ride. 

It is definitely a unique way to celebrate the start of fall by the coast, and the tickets must be reserved in advance as the cruise often sells out.

• Departure time: 4:15pm
• Round trip departure location: 43 Cape Henlopen Drive, Lewes
• Cost: $18 Adults;  $5 Children (6-13 years); $14 Senior & Others

The Gab Cinque Band at the Rusty Rudder

Dewey Beach’s Rusty Rudder is hosting a full day of live music, starting with Riley & Sean in the afternoon, followed by the Steve Lennon Duo in the early evening. 

The night closes out with the Gab Cinque Band, known for their high-energy indie rock sound that blends original songs with crowd-pleasing covers. 

With its bayside setting and relaxed atmosphere, the Rudder offers the perfect backdrop for an afternoon-to-evening of music by the water.

• Time: Shows starts at 3pm
• Location: 113 Dickinson Street, Dewey Beach

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Sippin’ with Sloths at Coastal Wilds

Spend a relaxed evening sipping wine and meeting the adorable sloths at Coastal Wilds. 

You’ll be able to enjoy the laid-back atmosphere alongside these famously slow companions.

Guests can enjoy personal sloth encounters, live music, and local wines in a peaceful outdoor setting. 

A complimentary glass of wine is already included, with additional drinks and snacks available for purchase on-site. 

• Time: From 6 to 8pm
• Location: 34215 Peppers Corner Road, Frankford
• Cost: $40

Live Music at Bluecoast Rehoboth

Enjoy a casual outdoor concert on Bluecoast’s patio, where local indie-rocker Maddox Gipko performs original songs and covers in a singer-songwriter style. 

Sit back with a cocktail or fresh seafood dinner while soaking up the seaside ambience and local tunes. 

This early-evening set is family-friendly and a great way to wind down after work.

• Time: From 4 to 7pm
• Location: 30115 Veterans Way, Rehoboth Beach
• Call (302) 278-7395 for more information

Beginners Watercolor on Gesso Boards at the Raye of Light Studio

This creative workshop introduces participants to painting the surf and sky on smooth gesso boards, a forgiving surface that’s perfect for beginners. 

Using watercolor blues and a touch of white gouache, you’ll learn how to layer, blend, and even lift color to shape your scene. 

Each person completes two square boards that can stand alone or be displayed together as a coastal-inspired diptych, with easels provided to showcase the finished pieces. 

It’s a fun, freeing experience that’s especially appealing to beach lovers and anyone curious about trying something new.

• Time: From 11am to 1pm
• Location: 117 Atlantic Avenue, Ocean View
• Cost: $48

Saturday, September 6th

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Chocolate Tasting in the Park

Satisfy your sweet tooth while supporting local parks with the FOCHSP Chocolate Tasting. 

Held indoors at the Officers’ Club in Cape Henlopen State Park, this tasting event lets you sample a variety of chocolate treats from local bakers. 

The admission (plus proceeds from a bake sale) benefits the Friends of Cape Henlopen State Park education fund. 

This is the perfect laid-back afternoon activity where foodies can mingle over cocoa creations, knowing they’re helping park programs at the same time.

• Time: From 1 to 4pm
• Location: Queens Road, Lewes
• Cost: $10

Full Moon Party

The season’s final Full Moon Party at Big Chill brings music, dancing, and community together under the glow of the night sky. 

Guests can enjoy a lively mix of DJ sets, glow sticks, and a silent disco experience with multiple playlists to choose from. 

Inspired by traditions that honor the full moon as a time for release and celebration, the evening invites everyone to let loose and soak in the energy of the coast. 

It’s a memorable way to say goodbye to summer while welcoming the spirit of fall.

• Time: From 6 to 9pm
• Location: 27099 Coastal Highway, Bethany Beach

Bethany Beach Boardwalk Arts Festival

The annual Bethany Beach Boardwalk Arts Festival transforms the town into a hub for creativity, showcasing the work of more than 100 juried artists. 

Visitors can explore paintings, jewelry, woodwork, ceramics, and more while strolling by the ocean. 

The festival kicks off the night before with an RSVP-only reception event at Gallery One, featuring wine tastings from Salted Vines Vineyard & Winery and light fare, giving early attendees a chance to mingle with the artists. 

During the day, a wine tasting sponsored by Beach Liquors adds a flavorful touch, offering a variety of pours alongside light bites. 

With so much to see and experience, the festival is a favorite for art lovers and a perfect way to spend the day by the shore.

• Time: From 10am to 5pm 
• Location: Downtown Bethany Beach (Boardwalk area)

Thunder Over The Waves Airshow with Cape May-Lewes Ferry

Experience an exhilarating day of aerial stunts and military flyovers during the Thunder Over the Waves Airshow. 

Spectators can watch jaw-dropping performances in Wildwood (NJ), including the Army Golden Knights parachute team, F22 Raptors, and a lineup of aerobatic demonstrations. 

With views stretching over the ocean and boardwalk, the show offers plenty of photo opportunities and memorable moments. 

• Time: Vehicles should arrive at 8am 
• Departure location: 43 Cape Henlopen Drive, Lewes
• Cost: $76 for one standard vehicle

Beatlemania Now! at the Milton Theatre

The Milton Theatre is hosting Beatlemania Now!, a Broadway-style stage show that performs note-for-note renditions of Beatles classics against 1960s video backdrops. 

Acclaimed as “extraordinary” by reviewers, the high-energy performance features a cast in period costumes delivering hits from Abbey Road, Sgt. Pepper and beyond. 

It’s a must-see nostalgic experience for Beatles fans and anyone who wants a lively glimpse into 60s pop culture.

• Hours: 3pm or 7:30pm
• Location: 110 Union Street, Milton
• Cost: $37 to $46 (varies by seat)

Youth Fishing Tournament

A kids’ fishing competition at Cape Henlopen State Park where young anglers (ages ~6–15) gather at the Lewes Fishing Pier to catch fish off the dock. 

Registration opens at 7am, and the fishing runs for 3 hours, with prizes awarded for the largest fish and most fish caught. 

The registration fee per child goes to the Friends of Cape Henlopen State Park, supporting youth programs. 

It’s an early-morning outdoor adventure that gets kids excited about nature and healthy competition.

• Time: From 8 to 11am
• Location: 15099 Cape Henlopen Drive, Lewes
• Registration fee: $10 

Tequila & Mexcal Dinner at Papa Grande's

Enjoy an intimate evening of Mexican cuisine and spirits at Papa Grande’s festive tequila room. 

Chef Emely has crafted a four-course menu paired with curated tequilas and mezcals, while a spirits specialist shares stories about the family producers behind each pour. 

Guests will savor dishes like crispy pork belly taquitos, fried chicken enchiladas, and a rich ancho-raspberry chocolate dessert, each thoughtfully matched with a signature cocktail or spirit. 

With limited seating, the event offers a cozy, immersive experience perfect for food and drink enthusiasts. 

• Time: From 6 to 9pm
• Location: 38929 Madison Avenue, Selbyville
• Cost: $95

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Delaware Bay Lights Cruise

Enjoy a scenic evening on the water with the Delaware Bay Lights Cruise, exploring the Lewes-Rehoboth Canal, Roosevelt Inlet, and the iconic Harbor of Refuge. 

Guests can admire both the East End and Harbor of Refuge lighthouses from nearby, capturing stunning views and memorable photos. 

Dolphin sightings are a frequent highlight, making each cruise a unique and exciting experience. 

This BYOB and snacks-friendly outing offers a relaxing, intimate way to experience the beauty of the Delaware Bay at sunset. 

• Time: From 5:30 to 7:30pm 
• Departure location: 217 Anglers Road, Lewes
• Cost: $40
• Before filling out the registration form, call (302) 226-3866 to check for availability

Royals at the Starboard

Royals bring a lively mix of modern hits to the Starboard, covering songs by artists like Taylor Swift, Bruno Mars, and Imagine Dragons. 

Their energetic performances create a fun, upbeat vibe that makes it easy to dance, sing along, or just enjoy the music with friends. 

It’s a great spot for anyone looking for a casual night out with familiar favorites and good company.

• Time: Starts at 10pm 
• Location: 2009 Coastal Highway, Dewey Beach

Decade 80 at Nalu

Decade 80 bills itself as “the band that owns the 80s”. 

They’ll play classic ’80s rock and pop hits (think Journey, Bon Jovi, Madonna, etc.) with high-energy performances and nostalgic flair. 

The party takes place at Nalu Surf Bar & Grill, making it a perfect late-night dance event for lovers of retro music and 80s culture.

• Time: From 9pm to 12am
• Location: 1308 Coastal Highway, Dewey Beach

Historic Lewes Farmers’ Market

The Historic Lewes Farmers Market (HLFM), which is a nonprofit organization committed to nurturing a vibrant local food system in Delmarva that is sustainable and socially responsible, is a hit for every farmer’s market lover.

It offers everything from fresh baked goods to home decor to fresh produce and homemade goodies.

It’s a wonderful spot to meet local growers and find seasonal ingredients, besides being a relaxed activity for food lovers and those who enjoy supporting small farms.

• Time: From 8am to 12pm
• Location: Johnson & Dupont Aves, Lewes

Sunday, September 7th

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21st Annual Cannonball 5k & Memorial Walk

The 21st Cannonball 5k Race & Trenny Elliott Memorial Walk returns to Lewes on Sunday, starting and finishing at the Lewes Historical Society. 

This flat, fast course winds through historic streets often called “the most beautiful race course in Delaware.” 

Runners and walkers alike can enjoy the scenic route while helping raise funds for the preservation of the Cannonball House, a landmark that survived the British bombardment of 1813 and now stands as a symbol of Lewes’ maritime heritage.

After the race, participants 21+ can celebrate with a complimentary beer at the Sussex Tavern, while awards, custom t-shirts, and refreshments round out the morning. 

Proceeds benefit the Lewes Historical Society, supporting the restoration of the Cannonball House for future generations.

• Time: Starts at 10am
• Location: 110 Shipcarpenter Street, Lewes
• Cost: $30 (online) $35 (day of race)
• Check out the race course

Surrender Yoga and Soundbath

Experience a slow-paced gentle yoga practice with supported, seated, and kneeling postures designed to release tension, improve flexibility, and restore balance, making it accessible for all levels. 

After yoga, immerse yourself in a soothing sound bath featuring crystal and Tibetan singing bowls, whose vibrations reduce stress, align chakras, and promote deep physical and emotional healing. 

This 90-minute session, or the standalone 30-minute sound bath, offers a calming escape to recharge your body, mind, and spirit.

• Time: From 7 to 8:30pm
• Location: 117 Atlantic Avenue, Ocean View
• Cost: From $20 (sound bath only); $50 (sound bath + yoga)

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Brunch & Kids Craft at Crooked Hammock Brewery

Sunday brunch here isn’t just about good food, it’s a full family outing. 

Alongside hearty dishes, mimosa flights, and Crooked Bloody Marys, kids get their own “party drinks” and weekly craft activities with local partners. 

On September 7th, the spotlight is on furry friends with Brunch with Boxers, Carolina Boxer Rescue will be on-site, sharing their mission and ways to get involved. 

Plus, 10% of sales from 10am to 4pm and all proceeds from the Orange Crush cocktail go directly to support the rescue.

• Time: From 10am to 2pm
• Location: 36707 Crooked Hammock Way, Lewes

Sunday Social Jam Night at the Listening Booth

End your weekend on a high note at The Listening Booth’s Sunday Social Jam Nigh.

This laid-back gathering is all about community and music, think less open mic, more collaborative jam session. 

Musicians of all levels are welcome to hop in, or you can just sit back with a drink and enjoy the live sounds. 

With rotating hosts and guest bartenders, every week brings a fresh twist, making it a fun, easygoing way to close out the weekend.

• Time: From 8pm to 12am
• Location: 18388 Coastal Highway, Lewes

Lewes Legends Evening Walking Tour

Step into Lewes’ darker past with this 90-minute evening walking tour that blends history with a touch of the paranormal. 

You’ll hear tales of the town’s 1631 founding and its tragic early massacre. 

Visit the unknown sailors’ cemetery at the Cape May–Lewes Ferry, and stop at landmarks like the Ryves Holt House and the Cannonball House, considered one of Delaware’s most haunted places. 

With eerie legends and strange happenings woven into Lewes’ history, it’s a unique way to experience the town after dark.

• Time: Starts at 6pm
• Location: 110 Shipcarpenter Street, Lewes
• Cost: Adults $15, Children (8–12) $5

All Weekend

Movie Screening of "Been Here, Stay Here"

Head to the theaters any day this weekend for this acclaimed documentary. 

Been Here, Stay Here explores life on Tangier Island (Chesapeake Bay) through the eyes of its residents as they face rising seas and waning land. 

The film has been praised for its intimate, immersive approach, showing a devout fishing community holding onto its traditions rather than fleeing the island.

Movies at the Midway screens it starting on September 5th, with multiple showtimes daily. 

• Location: 18585 Coastal Highway (Suite 1), Rehoboth Beach
• Check the theater schedule for exact times; ticket prices vary.

Dolphin Watching Cruise

Bring your binoculars and camera for a morning on the water with playful dolphins. 

Cape Water Tours runs a 1.5-hour cruise departing from the Lewes Ferry Terminal, searching the bay (and Atlantic if conditions allow) for wild dolphins. 

Along the way the boat passes the East End Lighthouse, Cape Henlopen Point, the Lewes Ferry terminal, and other landmarks. 

While dolphin sightings are not guaranteed, the guide says “it is likely” you’ll see these friendly marine mammals. 

• Departure location: Lewes Ferry Terminal
• Cost: $58
• Check out the available days and hours

Friends of Prime Hook Events

Prime Hook NWR is offering a variety of ways to connect with nature this weekend. 

On Saturday, September 6th, visitors can join a morning bird photography workshop with Ed Norman (now full) or sit in on an afternoon session with contest judges sharing what makes an award-winning wildlife photo. 

Bird lovers can also enjoy the First Saturday Bird Walk, a guided stroll along the refuge trails. 

The next evening, Sunday, September 7th, naturalist Julie will lead a walk timed with the sunset and full moonrise, creating the chance to take in the night sky while listening for nocturnal wildlife.

• Check their website for exact times and any required registration.

Which of these events are you most excited about? Share your plans in the comments, and don’t forget to follow our blog for weekly updates on Coastal Delaware’s best events and happenings!