Fall Fun in Southern Delaware!

Fall Fun in Southern Delaware!

Here are some fun events happening this fall in Southern Delaware, choose a few or do them all! Check our events calendar regularly for updated event information and share your favorite Southern Delaware fall activities with us on social media by tagging us! 



History is in reach of our Beaches! Check out our Fall for our History page here

Life is more inspired here! Check out our Arts Around our Towns page here


Fall Fun

Rehoboth Scarecrow Trail and ShowRehoboth Beach•Through October 31st

43rd Annual Nanticoke Indian PowwowMilton•Sep 10th

45th Annual Rehoboth Beach Fall Sidewalk SaleRehoboth Beach•Oct 1st

Lewes Fall Craft FairLewes•Oct 2nd

Historic Coastal Towns 4th Annual Cottage TourBethany Beach•Oct 9th

Dewey Goes PinkDewey Beach•Oct 9th

OktoBIRDfest x Dogfish HeadLewes•Oct 13th

Bark on the BoardsRehoboth Beach•Oct 16th

Milford Halloween ParadeMilford•Oct 20th

Canalside Inn Howl-weenRehoboth Beach•Oct 31st

Dewey Beach Trick or Treating and Haunted BonfireDewey Beach•Oct 29th

Boos and BrewsLewes•Oct 29th

Milton Wicked WeekendMilton•Oct 30th


Fall Flavors

6th Annual Southern Delaware Wine, Food, and Music FestivalMillsboro•Sep 18th

Rehoboth-Dewey Bacon FestDewey Beach•Sep 24th

9th Annual Broad Creek Bike and BrewLaurel•Sep 25th

Canalside Inn Craft Beer and Breweries Retreat​Rehoboth Beach•Sep 17th

Rehoboth Beach Garlic Fest •Oct 23rd

Tacomania•Oct 13th


Fall Fests

Hispanic FestivalGeorgetown•Sep 12th

Riverwalk Freedom FestivalMilford•Sep 18th

Base Ball at the Beach FestivalLewes•Sep 25th

The Big Draw FestivalMilford•Oct 2nd

Boast the CoastLewes•Oct 2nd

Wings and Wheels FestivalGeorgetown•Oct 2nd

Greyhounds Reach the BeachRehoboth Beach•Oct 6th

29th Annual Apple-Scrapple FestivalBridgeville•Oct 8th

Milton Zombie Fest •Oct 16th

31st Annual Sea Witch® FestivalRehoboth Beach•Oct 29th

Coastal Delaware Running Festival •Nov 12th


Fall for our Arts

The Marvelous WonderettesGeorgetown•Sep 10th

SSP presents CAUGHT IN THE NETMilford•Through September 19th

43rd Annual Bethany Beach Boardwalk Arts FestivalBethany Beach•Sep 11th

Lewes Artist's Studio TourLewes•Sep 18th

9th Annual True Blue Jazz Fest •Oct 13th

Rehoboth Beach Jazz FestivalRehoboth Beach•Oct 14th

THE ROCKY HORROR SHOWRehoboth Beach•Through October 31st

Autumn Art ShowSeaford•Sep 13th

Creative Market West RehobothRehoboth Beach•Monday's through October

OUR TOWNRehoboth Beach•Through September 26th


Fall Fun Anytime!

Admire the Fall Foliage

  • Trap Pond State Park is surrounded by vivid fall colors. Kayak the pond and its streams through the Bald Cypresses or walk and bike the trails on land.

  •  The Nanticoke Heritage Byway takes you through the beautiful rural landscapes of western Sussex County, including farm land, riverfronts, quaint towns, and more. 

  • Take the drive down Coastal Highway and enjoy the cool fall air as it breezes off the ocean. Stop in at any of our coastal towns for dining, shopping, and strolling. If you stop by Rehoboth Beach, check out their Scarecrow Contest and vote for your favorite!

Fall for Foodies

  • T.S. Smith & Sons in Bridgeville has all your fall favorites with apple picking, jams, honey and more.

  • Parson’s Farm offers a variety of seasonal u-picks including strawberries, blueberries, peaches, apples and pumpkins. 

  • Historic Lewes Fall Farmer’s Market runs from October 2–November 20 and features a wide variety of locally grown fall favorites, which you can browse in their open air market.