20 Things to Do at the Delaware Beaches This Fall

From shopping events to art and music festivals, here’s what you can’t miss this off season.

The True Blue Jazz Festival takes place in Rehoboth Beach from Oct. 16-20./Photo by Adobe Stock

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Sept. 19-21
21st Annual Chautauqua
“The 1960s in Delaware: A Decade of Turmoil and Transformation.” Noon-8 p.m.
Various locations in Lewes • 645-1148

Sept. 21
Lewes Artists Studio Tour
Artists and artisans open their private studios to the public. Admission is free. 10 a.m.-4 p.m.

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Sept. 27-29

2019 Fall Dewey Golden Jubilee
Nearly 200 goldens descends on Dewey to chase balls and swim in the surf.

Third Annual History Book Festival
More than 20 authors of fiction and nonfiction will be in downtown Lewes.

Sept. 28
5th Annual Southern Delaware Wine, Food and Music Festival
Sip wines from around the world paired with more than 20 coastal restaurants’ cuisine. The event also features live music and a culinary throwdown between chefs. Noon-4 p.m. See the website for pricing.
Independence Clubhouse, 23767 Samuel Adams Circle, Millsboro


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Oct. 4-6

43rd Annual Fall Sidewalk Sale
10 a.m.-8 p.m. (Store hours may vary.)
Rehoboth Beach, Dewey Beach and Route 1

Lewes Merchants Fall Sidewalk Sale
10 a.m.-5 p.m. daily.
Throughout the historic Lewes Commercial Districts.

Oct. 5

Lewes Historical Society Fall Craft Fair
Artisans and fine crafters gather on the society’s campus. 9 a.m.-4 p.m. Admission is $5 per person and free for children under 12.
Second and Shipcarpenter streets, Lewes • 645-7670

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Eighth Annual Dewey Goes Pink
The Starboard paints Dewey pink and organizes a 5K to raise money for the Delaware Breast Cancer Coalition. 11 a.m.-6 p.m. 
2009 Coastal Highway, Dewey Beach • 227-4600

Oct. 6
17th Annual Meals on Wheels Celebrity Chefs Brunch
Live music, craft beer garden, wine and brunch cocktails. 11 a.m.-2 p.m.
Rusty Rudder Restaurant, 113 Dickinson, St., Dewey Beach

Oct. 10-13
Greyhounds Reach the Beach
A weekend of events in Dewey and Rehoboth to celebrate greyhounds and raise funds to support greyhound adoption.

Oct. 16-20
True Blue Jazz Festival
Events are scheduled for venues in Lewes and Rehoboth Beach.

Oct. 17-20
Rehoboth Beach Jazz Festival
Held in several venues. This year’s artists include Gerald Albright, Boney James, Norman Brown and The Four Freshman.

Oct. 25-27
30th Annual Sea Witch Festival
Celebrate three decades of spooky fun with a costume parade, trick-or-treat, games and other activities.

Oct. 31-Nov. 10
Rehoboth Beach Independent Film Festival
American and international features, documentaries, and short films.
1701 Dartmouth Dr., Lewes • 645-9095



Nov. 2-3
35th Annual Rehoboth Art League Holiday Fair Fine Craft Show
Over 24 artisans will participate. $5 per adult. 10 a.m.-4 p.m.
Rehoboth Art League, 12 Dodds Lane, Rehoboth Beach • 227-8408

Nov. 22-24
Fifth Annual Dewey Beach Sip and Shop
Shop local this holiday season. 10 a.m.-5 p.m., Friday and Saturday; 10 a.m.-2 p.m. on Sunday.

Nov. 23
Rehoboth Beach Tree Lighting
Activities start at 6:30 p.m. at the Rehoboth Beach Bandstand.
229 Rehoboth Ave., Rehoboth • 227-6181

Nov. 29-30
25th Annual Southeastern Delaware Artists Studio Tour
Professional artists from the southeastern coastal Sussex County open their studios and galleries. 10 a.m. to 4 p.m.

Nov. 30
Dewey Beach Tree Lighting
Kick off the holiday season with Dewey’s annual tree lighting event.
Fifer Orchards Market, Dewey Beach • 228-3701

Looking for more things to do? Check out our community calendar here and our monthly event roundup here.

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