Delaware is wonderful in the fall for so many reasons – the cool and comfortable temperatures, the healthy harvests from our farms, and the colorful foliage that can be found from the city streets of Wilmington to the vast forests and marshlands around our beaches. It’s also prime time for celebrating with fall festivals. Two of the most popular are the Rehoboth Jazz Festival https://www.rehobothjazz.com/ and the True Blue Jazz Festival https://www.truebluejazz.org/. They don’t take place until mid-October but virtually every event at each sells out very quickly, so you need to make plans now if you want to attend.
In the meantime, here are some highlights from the Cape Gazette’s Fall Festival Guide for 2025 that you can plan for in September https://www.capegazette.com/article/fall-festivals-2025/295299.
CELEBRATE NATURE AND AGRICULTURE
Delaware’s own CHEER community for seniors will hold its Fall Festival at Trapp Pond on Friday, September 5th from 10 a.m. to 2 p.m. at Trap Pond State Park. There will be live music, line dancing lessons, games and prizes along with health and wellness information and a wonderful picnic lunch. Learn more at www.cheerde.com.
Beginning September 20th and running through November 8th, Fifer’s Farm in Wyoming will again celebrate fall family fun by opening up its scenic grounds for pumpkin picking, a corn maze and lots of other attractions. This is also a fall foodie fest, with homemade apple cider, kettle corn, cider donuts, lunch items and ice cream. Learn more at www.fifers.com.
VISIT OUR CULINARY COAST
Delaware’s beach towns offer some of the state’s most renowned restaurants and food-oriented special events. The Annual Chocolate Tasting in Lewes is a local favorite, happening this year on Saturday, September 6th from 1 to 4 p.m. at the Officer’s Club at Cape Henlopen State Park. All of the amazing offerings come from local households and proceeds go to the Friends of Cape Henlopen Education Fund for environmental education. Get the details at www.fochsp.org.
If you love crab cakes, lobster rolls, oysters, clam chowder and other maritime delights make plans for the Delaware Seafood Festival on September 20th at Schellville in Rehoboth. There will also be live music and cooking demonstrations, and all proceeds will go to the Center for the Inland Bays and the Delaware Restaurant Foundation. Get the details at www.delawareseafoodfestival.com.
STROLL, SHOP AND DINE IN HISTORIC DOWNTOWNS
Just over the border, Berlin, Maryland is a beautifully preserved town filled with shops and restaurants and also one that celebrates camaraderie with special events all year long. On Saturday, September 6th from noon to 5 p.m. the town will hold a Block Party on Main Street with food trucks, craft tents, special sales from quaint small businesses and face painting and games for kids. Learn more at www.berlinmd.gov.
Just two weeks later on September 19th and 20th, the town will also host the Berlin Fiddlers Convention in that same beautiful setting. The whole downtown will be filled with Celtic, old-time and Cajun music, with a competition for the best fiddle, banjo and guitar playing that will attract musicians from across Delmarva. There will be lots of food vendors and games for the kids. It happens on Friday the 19th from 6 to 10 p.m. and on Saturday the 20th from 11 a.m. to 5 p.m.
Also on Saturday, September 20th, downtown Milford will host the Riverwalk Freedom Festival. This is another family fun event with games, live entertainment, food vendors and the Duck Dash – a rubber ducky race on the Mispillion River. Get the details at www.milfordchamber.com.
BRING WONDERFUL ARTS AND CRAFTS INTO YOUR NEW HOME
Delaware has long been a destination for visual artists and craftspeople and fall tends to be prime time for festivals and fairs. The first big one will be on Saturday, September 6th from 10 a.m. to 5 p.m. when the Bethany Boardwalk Arts Festival brings more than 100 painters, photographers, sculptors, glass and woodworkers and jewelry makers to this seaside exhibition. There will also be a ticketed wine tasting and live music. It’s held rain or shine. Learn more at www.bethanybeachartsfestival.com.
The following weekend you can celebrate Delaware’s farming heritage at the Delaware Agricultural Museum Fall Craft Show. It happens on Saturday, September 13th from 10 a.m. to 3 p.m. and will offer handmade candles, jewelry, home décor, bath products and more. It’ll also be full of atmosphere, with historical reenactors demonstrating quilting, blacksmithing and spinning. Admission fees support the museum’s educational programs and preservation efforts, Get the details at www.agriculturalmuseum.org.
Also on Saturday the 13th from 10 a.m. to 5 p.m. the Indian River Marina Autumn Art Festival will bring more than 50 painters, photographers, pottery and jewelry-makers to Bethany. There will also be food trucks highlighting seafood, barbecue and desserts and lots of games for kids. Learn more at www.destateparks.com.
On Saturday, September 20th from 10 a.m. to 4 p.m. historic downtown Lewes will host the Lewes Artists Studio Tour. This unique event offers attendees a map showing the artists’ homes and studios. You’ll find wonderful paintings, photos, sculptures, ceramics and more, and can enjoy lunch at several downtown restaurants. Learn more at www.lewesartistsstudiotour.com.
ENJOY A GIRLS’ DAY OUT
On Friday, September 19th the Cambria Hotel in Rehoboth will host the Glitz & Glam Fashion Show to benefit the Harry K Foundation. There’s a luncheon beginning at 11 a.m. with models showcasing clothes, shoes and accessories from local boutiques until 2 p.m. Get the details at www.harrykfoundation.org.
MEET TODAY’S MOST FASCINATING STORYTELLERS
For the 9th year, Lewes will host the History Book Festival from Friday, September 26th through Sunday, September 28th. During the three-day event 22 authors of fiction and non-fiction books about compelling historical events and figures will be interviewed during educational sessions with plenty of time for audience Q & As. Get a list of the books and authors to be featured at www.historybookfestival.org.
THESE ARE JUST A FEW OF THE WONDERFUL FESTIVALS HAPPENING DURING SEPTEMBER. CHECK OUT THE CAPE GAZETTE’S FESTIVAL GUIDE FOR THE FULL LIST https://www.capegazette.com/article/fall-festivals-2025/295299.