October in Coastal Delaware is packed with events that celebrate the season with a mix of food, festivals, music, and community fun.
Whether you’re looking to stroll through a sidewalk sale, enjoy a seafood crawl, sip fine wines, or celebrate fall traditions, there’s something for everyone along the coast this month.
From Rehoboth Beach to Lewes and Millsboro, here are some of the top things to do in Coastal Delaware this October.
Rehoboth Beach/Dewey Beach Annual Fall Sidewalk Sale
This annual sale is a favorite for bargain hunters and casual shoppers alike.
Local shops line the streets with racks and tables full of discounted merchandise, making it the perfect time to stock up on fall fashion or unique coastal finds.
Beyond shopping, the festive atmosphere brings the community together for a lively weekend.
- Dates: October 3rd to 5th
- Locations: Rehoboth Beach, Dewey Beach, and Route One
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Argentinian Wine Dinner at Bluecoast Rehoboth
Food and wine lovers will enjoy an evening filled with bold Argentinian flavors paired with carefully selected wines.
The dinner features multiple courses, each crafted to highlight the region’s culinary traditions.
Guests can expect an intimate setting and expert wine pairings to elevate the experience. It’s the perfect night out for anyone who loves to indulge in fine dining by the beach.
- Date: Friday, October 3rd
- Time: 6 to 9pm
- Location: 30115 Veterans Way, Rehoboth Beach
- Cost: $114 per person
Crab Crawl — Rehoboth Beach
This event is a seafood lover’s dream, offering a chance to enjoy crab prepared in different styles from various participating restaurants.
Each stop along the crawl adds its own unique flavor and atmosphere, so attendees can explore Rehoboth while tasting their way through this local tradition.
It’s a fun mix of great food, community spirit, and coastal charm.
- Date: Saturday, October 4th
- For more info, email [email protected]
Boast the Coast Maritime Festival
Celebrate Lewes’ maritime heritage with a day filled with history, culture, and family-friendly activities.
Visitors can explore exhibits, meet local artisans, enjoy nautical-themed entertainment, and experience the town’s deep connection to the sea and its traditions.
It’s a must for anyone who loves coastal history and community celebrations.
- Date: Saturday, October 4th
- Time: 11am to 2pm
- Location: 1812 Memorial Park, Lewes
The Life of a Showgirl Brunch
Join fellow Swifties at Big Oyster Brewery for a celebratory brunch, where Taylor Swift’s The Life of a Showgirl takes center stage.
Sing along to the songs, sip cocktails or mocktails, and channel your creativity by painting your own limited edition vinyl record.
The vibe will be playful, festive, and full of music lovers sharing in that new-album energy.
It’s the perfect mid-day gathering if you want good food, good tunes, and a fun way to enjoy Taylor’s latest release.
- Date: Sunday, October 5th
- Time: 12 to 3pm
- Location: 1007 Kings Highway, Lewes
- Cost: $18
Sposato Wine Tasting at Bluecoast Rehoboth
Guests will have the chance to sample a curated selection of wines from Sposato Vineyards.
The tasting offers an approachable yet refined experience for both seasoned wine lovers and casual enthusiasts.
Each pour is designed to showcase the vineyard’s unique character and craftsmanship, an ideal midweek escape to savor and socialize.
- Date: Wednesday, October 8th
- Time: 4 to 6pm
- Location: 30115 Veterans Way, Rehoboth Beach
- Cost: $35 per person
Rehoboth Beach Museum's Beach Ball Gala
The Beach Ball Gala is an elegant evening that combines coastal charm with community spirit.
Guests can enjoy fine dining, live entertainment, and dancing while supporting the preservation of local history.
The gala is also a chance to connect with neighbors, business leaders, and supporters of the arts in a festive, upscale setting.
As one of Rehoboth’s premier social events of the year, it’s the perfect blend of glamour and purpose.
- Dates: October 9th to 11th
- Location: 511 Rehoboth Avenue, Rehoboth Beach
- Cost: $95-$175
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Greyhounds Reach the Beach
Dog lovers and greyhound adopters gather for this unique event celebrating retired racing greyhounds.
Visitors can meet these gentle dogs, participate in activities, learn about adoption opportunities, as well as vendors and social gatherings for pet owners.
It’s a heartwarming weekend that combines fun, education, and community.
- Dates: October 9th to 11th
- Location: 229 Rehoboth Ave, Rehoboth Beach
- Cost: $30 (online); $35 (at the door)
Schellville Fall Harvest Fest
Schellville transforms into a magical autumn wonderland during the Fall Harvest Fest, making it a must-visit for families and fall enthusiasts.
Visitors can enjoy seasonal activities like pumpkin crafts, hayrides, and cozy treats that capture the spirit of the season.
The vibrant decorations and family-friendly atmosphere create a picture-perfect backdrop for making memories.
It’s one of the most festive and charming ways to welcome fall in Coastal Delaware.
- Dates: October 11th to 12th
- Time: 5 to 8pm
- Location: 36470 Seaside Outlet Drive, Rehoboth Beach
- Cost: $10 for ages 2+
OktoBOARDfest!
Join the community at The Starboard for OktoBOARDfest!, an Oktoberfest-style celebration with a lively twist.
Expect festive music, beer specials, and a cheerful crowd decked out in German-inspired attire, all set against the backdrop of Dewey Beach.
With a relaxed, daytime vibe, it’s perfect for enjoying good company, cold drinks, and a playful take on fall festivities.
Whether you’re coming with friends or family, this event brings beachside charm and a taste of Bavarian fun to Coastal Delaware.
- Date: Saturday, October 11th
- Time: 1 to 6pm
- Location: 2003 Coastal Highway, Rehoboth Beach
Boardwalk Buddy Walk
The Boardwalk Buddy Walk is a heartwarming community tradition that raises awareness and celebrates individuals with Down syndrome.
Families, friends, and supporters gather on the iconic Rehoboth Beach Boardwalk for an inspiring morning of unity and inclusion.
The walk is filled with energy, smiles, and encouragement, creating a memorable experience for participants and onlookers alike.
It’s more than just a walk, it’s a celebration of diversity and the strength of community.
- Date: Saturday, October 11th
- Time: Walk starts at 9am
- Location: Rehoboth Beach Bandstand
Clothing Our Kids
This charity event supports local children in need by raising funds for clothing programs.
The gathering blends community engagement with fundraising in an impactful way, guests can look forward to an inspiring day filled with purpose and generosity.
Attending means supporting a vital cause while connecting with others who care.
- Date: Monday, October 13th
- Time: 10:30am to 5pm
- Location: 32981 Peninsula Esplanade, Millsboro
- Cost: $250
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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
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+
Lewes Brewing Co. Beer Dinner at Crust & Craft
Craft beer meets creative cuisine at this special dinner pairing event that is perfect for both beer enthusiasts and foodies.
Each course is designed to complement unique brews from Lewes Brewing Co., so the guests can enjoy an evening of flavor exploration in a relaxed setting.
- Date: Wednesday, October 22nd
- Time: 6:30 to 9pm
- Location: 18701 Coastal Highway, Rehoboth Beach
- Cost: $72 per person
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Sea Witch Festival
The Sea Witch Festival is Coastal Delaware’s biggest fall celebration, drawing crowds from near and far for a weekend of Halloween fun.
From the colorful costume parade to trick-or-treating, live entertainment, and a packed vendor fair, there’s something for every age.
Families love the kid-friendly activities and contests, while adults can enjoy the lively downtown atmosphere and seasonal treats.
It’s the signature October event in Rehoboth Beach and a tradition you won’t want to miss.
- Dates: October 24th to 26th
- Schedule of Activities (Items highlighted in red are confirmed)
Spooky Tunes & Tales
Step into an evening of ghostly fun with a mix of haunting stories and live music that sets the perfect Halloween mood.
Professional storytellers bring local legends and spooky folklore to life, while musicians add an eerie soundtrack that keeps the audience on edge.
The intimate setting makes every tale feel chillingly real, creating an experience that’s both festive and spine-tingling.
- Date: Saturday, October 25th
- Times: 3pm and 6pm
- Location: 17701 Dartmouth Drive, Lewes
- Cost: $30 (general); $80 (VIP table)
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