One weekend, but countless ways to celebrate the season! Coastal Delaware is buzzing with energy, creativity, and Halloween spirit. 

No matter if your vibe is artsy, adventurous, or just ready for some coastal fun, this weekend promises to be one for the memory books.

Doors of Fame Exhibition

At the Rehoboth Art League, history and creativity come together in the Doors of Fame Exhibition. 

These iconic doors, signed by more than 285 artists, community members, and notable figures, celebrate over 85 years of artistic legacy in Delaware. 

Alongside this historic display, visitors can explore the League’s remarkable collection of mid-20th-century artworks, colonial furniture, and rare artifacts that tell the story of local artistry and cultural evolution.

• Dates: May 1, 2025–October 31, 2025
• Time: Mon-Sat: 10am-4pm; Sun: 12-4pm
• Location: 12 Dodds Lane, Rehoboth Beach

Hopkins Fall Festival

Celebrate autumn at Hopkins Farm with a full lineup of family-friendly activities and entertainment. 

Visitors can enjoy tractor rides across the scenic fields, get creative with pumpkin painting, and explore the straw maze. 

The farm atmosphere comes alive with live music, storytime sessions, and the chance to meet farm animals at the Cape Henlopen FFA Petting Zoo. 

Guests can savor breakfast at Jefferson Lodge or sample delicious local fare throughout the day.

• Days: Saturdays and Sundays during October
• Time: 9am to 3pm
• Location: 18186 Dairy Farm Road, Lewes

True Blue Jazz Festival

Jazz lovers will delight in this multi-day festival featuring performances from local and national artists. 

Venues throughout Rehoboth and Lewes host intimate shows, jam sessions, and special events. 

The festival showcases both established names and rising talent in the jazz scene, making it a must-attend for music fans looking for soulful coastal nights.

• Dates: October 15th to 19th
• Location: Rehoboth Beach & Lewes
• View the festival lineup 

Reefer Madness at Clear Space Theater

Get ready for a high-energy, laugh-out-loud ride with Reefer Madness, the hilariously over-the-top musical satire playing at Clear Space Theatre in Rehoboth Beach. 

Inspired by the 1936 propaganda film, the show follows clean-cut Jimmy Harper as his life spirals into absurd chaos under the influence of “Mary Jane.” 

With witty lyrics, lively jazz-inspired numbers, and sharp social satire, this cult favorite from the creators of Heathers: The Musical delivers a mix of frolic, mayhem, and irresistible humor.

• Various dates and times
• Location: 20 Baltimore Avenue, Rehoboth Beach
• Cost: $32-$52

The Rocky Horror Show: LIVE

Step into a world of outrageous fun and cult-classic energy as The Rocky Horror Show: LIVE returns to the Milton Theatre. 

This beloved in-house production is a local favorite, blending rock and roll, sci-fi, and cheeky humor into an unforgettable live experience. 

With its vibrant cast, dazzling performances, and infectious energy, the show invites audiences to sing, dance, and fully embrace the wild, electrifying spirit of this timeless favorite

• Various dates and times
• Location: 110 Union Street, Milton
• Cost: $32-$52

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Oh the Horrors! Film Trailer Challenge

Calling all filmmakers and fright lovers, the Milton Theatre transforms into a horror haven for the annual Horror Trailer Challenge. 

Hosted by Revival House Films, this unique competition invites creators to produce their own horror trailers and screen them before a live audience. 

Contestants have the thrill of seeing their chilling visions come to life on the big screen while competing for cash prizes. 

So, If you are a filmmaker or a fan, this will be an unforgettable night that celebrates creativity and the love of scary cinema.

• Date: Friday, October 17th
• Time: Doors open 6:30pm
• Location: 110 Union Street, Milton
• Cost: $8-$14

Elvis at Cottage Cafe!

Experience the magic of Elvis as Frank “ELVIS” Raines takes the stage at the Cottage Café in Bethany Beach. 

Enjoy an evening filled with classic tunes, lively performances, and a fun atmosphere that brings the King’s energy to life. 

Guests can dine on the Cottage’s famous burgers, crab cakes, and a wide selection of entrees while soaking up the show.

• Date: Friday, October 17th
• Time: 5 to 8pm 
• Location: 33034 Coastal Highway, Bethany Beach

Cline Family Cellars Wine Dinner

Fish On presents a sophisticated culinary evening featuring wines from the renowned Cline Family Cellars of Sonoma County. 

Guests will be treated to a five-course meal crafted by Chef Ian, each dish artfully paired with a complementary Cline vintage. 

From the first sip to the last bite, the dinner highlights seasonal ingredients and the winemaker’s rich California heritage.

The event offers a relaxed yet elegant atmosphere, perfect for wine enthusiasts and food lovers.

• Date: Friday, October 17th
• Time: 6 to 9pm
• Location: 17300 North Village Main Boulevard, Lewes
• Cost: $114

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Milton Library's 150th Anniversary Gala

Celebrate a century and a half of community, knowledge, and connection at Milton Library’s 150th Anniversary Gala. 

Guests can enjoy live music, complimentary food and drinks provided by local favorites like Irish Eyes, The Doughbar, Zava Café, Dogfish Head, and Twin Branch Winery. 

The evening will also feature a silent auction and raffles with exciting prizes. 

Casual attire is welcome, and attendees can choose between ticket options that include non-alcoholic beverages or two alcoholic drinks.

• Date: Saturday, October 18th
• Time: 4 to 6pm
• Location: 121 Union Street, Milton
• Cost: $25-$35

Zombie Fest: Apocalypse

Get ready for a night of spooky fun as Hudson Fields transforms into a post-apocalyptic playground. 

Zombie Fest: Apocalypse features live entertainment, themed activities, and plenty of eerie surprises for all ages. 

Guests are encouraged to dress in their best zombie attire to fully embrace the atmosphere. 

• Date: Saturday, October 18th
• Time: 4 to 9pm
• Location: 30045 Eagle Crest Road, Milton
• Cost: $5 for ages 12+

Wicked Brew Bash & Dilly Dally!

The Wicked Brew Bash brings together the best of local craft beer and wine, as guests can have unlimited tastings while enjoying live music by Kleptoradio. 

Costumes are highly encouraged, food trucks and artisan shacks will be on-site, and while the roller rink is closed, the sledding hill and train rides remain open for added fun.

You can also participate in the Dilly Dally, a whimsical ride along the Junction & Breakwater Trail, for an additional $10. 

Participants are encouraged to wear costumes, decorate their bikes, and enjoy a joyful, non-competitive “cruise” that raises funds for Celebrate Wellness, a nonprofit supporting mental health for hospitality workers. 

Riders can choose their distance, from five miles to a full ride into Lewes, with fun surprises along the way. 

After that, participants can join the Wicked Brew Fest at Schellville to continue the celebration.

• Date: Saturday, October 18th
• Time: 3:30 to 5:30pm (Dilly Dally); 5 to 8pm (Wicked Brew Fest)
• Location: 36470 Seaside Outlet Drive, Rehoboth Beach
• Cost: Cost: $25 (Wicked Brew Bash); $35 (Wicked Brew Bash + Dilly Dally); $12 (Dilly Dally)

Lace Up for Ag Literacy 5K Run/Walk

The Lace Up for Ag Literacy 5K Run and Walk invites participants to enjoy the beauty of Hopkins Farm while supporting agricultural education. 

The off-road course winds through scenic pastures, hay bales, and farm bridges, offering a unique countryside running experience. 

This family-friendly event celebrates Delaware’s farming community and promotes the importance of local agriculture. 

Participants receive commemorative shirts and awards, and even those who cannot attend can support as “Silent Heroes.” 

Proceeds benefit the Delaware Farm Bureau Foundation, helping to fund educational programs and outreach across the state.

• Date: Saturday, October 18th
• Time: Starts at 9am (Healthy Kids Run starts 8:50am)
• Location: 18186 Dairy Farm Road, Lewes
• Cost: $30-$35

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Sussex SuperHero 5K

Cape Henlopen State Park becomes a gathering place for everyday heroes during the Sussex SuperHero 5K. 

Participants are encouraged to channel their inner hero while running or walking to support local charitable initiatives. 

Proceeds go toward providing shoes and supplies to students in need and aiding the TidalHealth Nanticoke Patient Assistance Fund. 

The run promotes fitness, fun, and community spirit while celebrating the power of perseverance and compassion. 

Whether in costume or casual gear, every participant can make a heroic impact.

• Date: Sunday, October 19th
• Time: Starts at 9am
• Location: 15099 Cape Henlopen Drive, Lewes
• Cost: $35-$40

Spook-tacular Halloween Brunch

Get ready for a ghoulishly good time at the Hammock with their Spook-tacular Halloween Brunch. 

Guests can indulge in a hauntingly delicious menu featuring themed favorites like the Monster Smash Burger and Franken Berry French Toast. 

Festive cocktails and mocktails, such as the Witch’s Brew and Bloody Scary, add a playful twist to the celebration. 

Kids will enjoy spooky crafts, costume contests, and other Halloween surprises designed just for them. 

• Date: Sunday, October 19th
• Time: 10am to 2pm
• Location: 36707 Crooked Hammock Way, Lewes

The Young Fables

The Young Fables, a Nashville-based duo composed of Laurel Wright and Wesley Lunsford, bring their heartfelt country-pop sound and captivating storytelling to the stage. 

Known for their authentic performances and soulful harmonies, the pair use their music to shine a light on important social causes.

This special show at the VIA Clubhouse is dedicated to raising awareness for victims of domestic violence.

• Date: Sunday, October 19th
• Time: 5 to 7pm
• Location: 415 North Boardwalk, Rehoboth Beach
• Cost: $35

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Spooktacular

The Spooktacular is a family-friendly event packed with activities and attractions with a spooky twist.

Children can dive into classic fall fun with pumpkin decorating and the corn pit, while face painting, costumed characters, balloon twisters, and the Hayride Express bring extra magic to the evening. 

Guests can also lace up for the skating rink, try the sled hill, or play in the snow zone for a wintry surprise. 

To round out the experience, food trucks, snack shacks, and local breweries will be on-site to keep everyone fueled throughout the night.

There is also a Special Needs Hour from 4 to 5pm, designed specifically for families of all ages with special needs to enjoy the activities in a quieter and more accommodating setting.

• Date: Sunday, October 19th
• Time: 4 to 8pm
• Location: 36470 Seaside Outlet Drive, Rehoboth Beach
• Reservations are required

Love discovering what’s happening around Coastal Delaware? Keep following our blog for weekly updates on local events, festivals, and hidden gems along the shore. 

There’s always something new to explore, don’t miss out on what’s next!