Top September Events in Delaware You Should Attend

September is a fantastic time to visit Delaware! The weather is perfect for outdoor activities, and the state hosts a variety of exciting events. From charming festivals to live entertainment, here’s your ultimate guide to the best events happening in Delaware this September.

1. Delaware State Fair - September 1-5, 2025

The Delaware State Fair is a beloved tradition that combines agriculture, entertainment, and local culture. This year, it returns with carnival rides, live music, food stalls, and animal exhibits. Whether you want to try a deep-fried treat or watch a rodeo, the fair is fun for the whole family.

  • Where: Harrington Fairgrounds

  • What to Expect: Rides, food vendors, live entertainment

  • Best for: Families, foodies, and anyone looking for classic fair fun

2. Rehoboth Beach Autumn Jazz Festival - September 10-12, 2025

The Rehoboth Beach Autumn Jazz Festival is one of Delaware's premier music events. This three-day festival showcases some of the best jazz musicians, with performances set against the beautiful backdrop of Rehoboth Beach. It’s a must-attend for music lovers and anyone who enjoys a relaxing, high-class vibe.

  • Where: Rehoboth Beach Convention Center and various venues

  • What to Expect: Live jazz music, local food and drink

  • Best for: Jazz enthusiasts, couples, music lovers

3. Delaware Wine and Beer Festival - September 18, 2025

For wine and craft beer lovers, the Delaware Wine and Beer Festival is the event to attend. This one-day festival brings together local wineries and breweries for tastings, live entertainment, and food trucks. It’s an excellent opportunity to discover Delaware’s best wines and brews.

  • Where: Delaware Agricultural Museum and Village, Dover

  • What to Expect: Wine tastings, craft beers, live music

  • Best for: Wine lovers, beer enthusiasts, foodies

4. The Great Delaware Pumpkin Festival - September 24-26, 2025

As the fall season kicks off, the Great Delaware Pumpkin Festival is an event for the whole family. With pumpkin decorating contests, pumpkin-themed food, hayrides, and live music, this festival is a perfect way to celebrate the start of autumn in Delaware.

  • Where: Delaware Agricultural Museum and Village, Dover

  • What to Expect: Pumpkin-themed activities, live music, food vendors

  • Best for: Families, kids, fall lovers

5. Lewes Historical Society Antique Show & Sale - September 25-26, 2025

If you're a fan of antiques, don’t miss the Lewes Historical Society Antique Show & Sale. Held annually in September, this event features over 60 antique dealers selling furniture, art, jewelry, and other collectibles. Whether you're a collector or just browsing, it’s a great way to experience the charm of Lewes, Delaware.

  • Where: Lewes Historical Society Grounds

  • What to Expect: Antique dealers, collectibles, outdoor shopping

  • Best for: Antique lovers, collectors, history enthusiasts

September is one of the best months to visit Delaware with its combination of outdoor festivals, live music, and family-friendly activities. From jazz at the beach to a pumpkin festival in Dover, there’s something for everyone to enjoy. Make sure you mark your calendar for these top events happening across Delaware this September!

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