September Events in Coastal Virginia: Fall Festivals, Concerts & Community Fun

Fall, y’all—it’s finally here! 🍂 September in Coastal Virginia is one of my favorite times of year. The weather is dreamy, the summer crowds start to fade, and the events calendar absolutely comes alive. From beach festivals to food truck rallies to art shows and live music—this region knows how to kick off fall with style.

Whether you’re a new neighbor or a longtime local, here are some can’t-miss events happening in Virginia Beach, Chesapeake, and beyond this September!

🎡 51st Annual Neptune Festival – Virginia Beach Oceanfront

This legendary local tradition celebrates everything we love about life on the coast. Held every September at the Virginia Beach Oceanfront, the Neptune Festival includes an arts & crafts show, live music, food vendors, surfing competitions, and even a giant sand sculpture championship. Mark your calendar—it’s one of the biggest events of the year!

🎨 Chesapeake Rotary Craft Beer & Wine Festival

If you love sampling local beer, wine, and cider—this is your jam. This annual event takes place in mid-September at Chesapeake City Park, featuring dozens of regional vendors, food trucks, and live music. Grab your lawn chair and make a day of it! (21+ event, but kid-friendly space nearby if you’re juggling both.)

🖼️ Virginia Beach Art Show at Town Center

Support local artists, browse beautiful handmade goods, and find a new favorite piece for your home! This open-air event happens in early September and showcases everything from pottery to photography. Great for a Saturday stroll and a perfect excuse to grab brunch while you’re there.

🎶 YNot Wednesdays at Town Center (Final Concerts of the Season!)

Free live music, cool breezes, and room to dance? Yes, please. September marks the end of this beloved summer concert series, so be sure to catch the final few shows on the Town Center Plaza green. Bring your lawn chairs and your dancing shoes—this is always a good time!

🚜 Bergey’s Corn Maze & Fall Market – Chesapeake

This family-owned dairy farm opens its gates for fall fun starting in mid-to-late September. Get lost in the corn maze, pick a pumpkin, grab a milkshake, and say hi to the goats! Bergey’s Breadbasket is a wholesome (and adorable) way to welcome fall with the whole family.

🎭 Sandler Center Performances

Ready for a cozy night out? The Sandler Center for the Performing Arts offers concerts, theater, comedy, and cultural performances all month long. It’s the perfect date night or friends’ night out—plus there are great restaurants within walking distance.

🧁 Chesapeake Jubilee Fall Craft Market

Craft lovers, rejoice! This sweet little event features local artisans, handmade decor, jewelry, and fall-themed goodies. It’s a great way to support small businesses and get a head start on seasonal decorating—or even holiday shopping (yes, I said it!).

Pro tip: Many events offer free admission and free parking, but bring cash or a card for local vendors and food trucks. Some spots are pet-friendly too, so check event details before you leash up your pup!

September is the perfect time to fall in love with your city all over again—or for the very first time. Whether you’re walking through an art fair, toe-tapping at a concert, or getting lost in a corn maze, there’s no better way to feel connected to your community.

Looking for a home near all the local action? I’d love to help! Let’s find your place in Coastal Virginia.