Get outdoors this fall and enjoy Southern Delaware’s charms

September is one of the best times of year to enjoy Southern Delaware. The beaches are uncrowded, hotel and rental rates are lower, and the weather and water are sublime. Plus, there are many festivals and outdoor activities to enjoy beyond the beaches.

 Fall festivals aplenty 

Riverwalk Freedom Festival, Sept. 11, Milford

The 14th Annual Riverwalk Freedom Festival features the Smile for Freedom 5K, then Operation Giveback (to support active duty military and veterans) with fireworks, live entertainment, and food vendors. There will also be craft vendors, bike and car shows, and a kids’ corner. (


Nanticoke Indian Powwow, Sept. 12, Millsboro

The noun “powwow,” from the Narragansett Eastern Algonquian language, is defined as any gathering of Native American people. Skilled Native American artisans travel across the country to attend various powwows to display and sell their handmade goods. It is a welcome opportunity to visit with friends and relatives, renew acquaintances, and trade or sell Native American arts and crafts, including jewelry, pottery, moccasins, ribbon shirts, shawls, dream catchers, and paintings. (


Bethany Beach Boardwalk Arts Festival, Sept. 12, Bethany Beach

Join more than 100 skilled artisans at a premier fine arts festival set against the backdrop of the Atlantic Ocean on the beautiful Bethany Beach boardwalk and surrounding streets. (


Woodland Ferry Festival, Sept. 12, Woodland

The festival takes place along the Woodland Church Road in the small community of Woodland, home of the historic Woodland Ferry. Local nonprofit organizations present information on the Nanticoke River, its watershed, and area history. There will be fun activities for kids and entertainment. (

Freeman Stage Arts and Jazz Festival, Sept. 19, Selbyville

A day not to be missed at The Freeman Stage at Bayside. Stroll the green and enjoy previewing the artwork of Delmarva’s finest artists. Pull up a chair and groove to some of the most talented jazz artists to ever play at the shore. The Arts and Jazz Festival will make the last weekend of the summer one of the most memorable. Free for all. (


The Farmer and Foodie Festival and Art Crawl, Sept. 13, Georgetown

Stop by the Georgetown Circle for the Farmer and Foodie Festival celebrating the local farming community. Enjoy cooking demonstrations, beer and wine tastings from local breweries and vineyards, carriage rides, live entertainment, pumpkin decorating for the kids, and a backyard barbecue competition. (


Millsboro Country Festival, Sept. 20, Millsboro

The Millsboro Country Festival stars The Tennessee Mafia Jug Band. The fun starts at 11:00am at Millsboro Little League Field. There will be redneck games and kids’ games, Fast Action Motor Sports, craft vendors, live entertainment, and food vendors with good country cooking you don’t want to miss. (


Hike, bike and swim

The Breakwater Junction Biking/Hiking Trail is an historic rail trail connecting Lewes and Rehoboth Beach. Few visitors realize that just beyond the hustle and bustle of the outlets there is all of this pristine coastal beauty to explore.

lake-539716_1280Named after the rail line that once ran between Lewes and Rehoboth and carried passengers to the Methodist resort camps along the Atlantic Ocean, the hiking/biking/strolling trail runs for approximately 5 miles through coastal marshes, woods, and farm fields. The crushed stone trail is smooth and easy to navigate and has interpretive signs about the local flora and fauna. It features an 80-foot-long railroad bridge constructed in 1913 which provides the hiker with beautiful views of coastal marshes and a World War II “Ghost Tower” that was part of the East Coast’s defense system.

Sept. 19 is the day for Southern Delaware’s premier cycling event, the Tour de Sussex Bike Tour. Starting at the Delaware Technical Community College in Georgetown at 8:00am, rain or shine, participants can ride distances of 25, 50, 62 and 100 miles. Register by Aug. 31 and pay $65, or between Sept. 1–19 for $75. The fee includes SAG support, T-shirt, lunch, maps, and rest stop refreshments. The rest stops are fantastic this year and include Dogfish Head Brewery, Irish Eyes, Papa Grande’s, and beautiful Trap Pond State Park.

“Escape Lewes” is a Sept. 27 event for the adventurous athlete. It includes an open water 5K and 1-mile swim. The starting line is a bit unusual because it involves jumping off the Cape May-Lewes Ferry! Categories include Wetsuit and Non-Wetsuit, and Junior, Masters, and Triathlon Club categories. It is a flat open-water swim that takes place in the Delaware Breakwater in the National Harbor of Refuge.


For more information 

Southern Delaware Tourism: 


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