Autumn at the Coast: Must-Attend Delaware Fall Festivals & Events!
There are so many reasons to love the autumn months around Sussex County—including cool, sunny days on uncrowded beaches, abundant harvests from our local farms, and festivals celebrating wonderful fall traditions. Here are a few highlights happening this season!
The Rehoboth Beach Fall Sidewalk Sale
October 2–4 | Downtown Rehoboth Beach & Route 1 / Dewey Beach
Find wonderful bargains on sidewalk racks, tables, and inside local shops, rain or shine!
Wings & Wheels
Saturday, October 3 (10:00 AM – 4:00 PM) | Delaware Coastal Airport, Georgetown
(Dinner party held the night before on Friday, October 2)
Showcasing vintage aircraft, classic cars, military vehicles, and live entertainment.
Hook & Ladder Oktoberfest
Saturday, October 3 (12:00 PM – 4:00 PM) | Rehoboth Convention Center
Spotlighting offerings from local breweries, bourbon, and moonshine, alongside live music, food, and local vendors. Proceeds benefit the Rehoboth Beach Volunteer Fire Company.
Boast the Coast Maritime Festival
Saturday, October 3 (11:00 AM – 2:00 PM) | Lewes City Dock & Canalfront Park
A local favorite featuring family activities, boat tours, nautical displays, and special downtown shop offerings.
Coast Day
Sunday, October 4 | Hugh R. Sharp Campus, Lewes
Hosted by the University of Delaware at the end of Pilottown Road, featuring interactive, educational maritime exhibits for all ages.
CHEER Fall Craft Fair
Saturday, October 3 | CHEER Community Center, Georgetown
Featuring seasonal artwork, crafts, and gifts from local artisans.
Apple Scrapple Festival
Friday & Saturday, October 9–10 | Bridgeville
A homegrown favorite with scrapple dishes, apple treats, live music, carnival rides, and the Miss Apple Scrapple pageant!
Hopkins Farm Fall Festival
Friday – Sunday, October 9–11 | Hopkins Farm, Dairy Farm Road
Enjoy a 5K race, live music, and agricultural exhibits at this beautiful family farm.
Mid-Atlantic Symphony Horn Trio & Piano Trio
Saturday, October 10 | Epworth United Methodist Church
An afternoon of classical chamber music performance.
Punkin Ale Fest
Saturday, October 10 | Dogfish Head Brewery, Milton
Celebrating seasonal libations, live music, local vendors, and family fun. Benefits the Brandywine Valley SPCA, who will be on-site with adoptable dogs!
Seaford Community Fall Festival
Sunday, October 18 | Governor Ross Mansion
Featuring trunk-or-treating, wagon rides, face painting, crafts, food, and a petting zoo.
Milford Community Parade
Wednesday, October 21 (Starts at 6:30 PM) | Walnut Street, Milford
Marching bands and creative floats built around this year's theme: "Comic Books Come to Life."
Boos & Brews
Friday, October 23 | Historic Lewes
Put yourself in the Halloween spirit with food, beverages, and seasonal fun.
Sea Witch Festival
Friday – Sunday, October 23–25 | Downtown Rehoboth Beach
One of the year's biggest coastal events! Features costume parades, live entertainment, contests, games, and the Sea Witch 5K.
Pumpkin Festival on the Broadkill
Saturday, October 24 | Milton Fire Department
Over 50 vendors, pumpkin treats, baked goods, pumpkin painting, a petting zoo, and more.
Wags, Witches & Warlocks
Saturday, October 24 | Downtown Bethany Beach
Enjoy a costumed parade through town and a free noon performance of Puppy Pals Live at the Bandstand!
All Hallow’s Eve & Wicked Weekend
Saturday, October 31 | Lewes & Milton
Cap off the month with folklore and history at the Lewes Historical Complex (All Hallow’s Eve), or head to Milton Memorial Park for a spooky evening of family-friendly fun (Wicked Weekend).
One Final Note:
As real estate professionals who live, work, and play right here in Sussex County, we don't just know these communities—we call them home! Fall is our absolute favorite time of year to enjoy everything our coastal towns have to offer alongside our neighbors. Whether you're a long-time resident or looking to make the Delaware beaches your permanent retreat, we’d love to connect. What's your favorite local festival to attend each autumn? Let us know, and we hope to see you around town this season!