
August 31, 2026
September is one of my favorite months in Coastal Virginia.
The summer crowds begin to thin out, the weather starts to cool (just a little), and some of the biggest events of the year take over Hampton Roads. Whether you’re looking for live music, family festivals, incredible military aviation, or a weekend by the water, there’s something happening almost every weekend.
Here are a few events worth adding to your calendar this September.
The world’s largest women’s action sports festival makes its Virginia Beach debut, bringing together elite athletes, live music, fitness classes, inspiring speakers, and family-friendly activities along the Oceanfront.
📅 September 5–7, 2026
Watch world-class surfing competitions, browse interactive vendor villages, enjoy free concerts, and experience a weekend dedicated to empowering women and girls through sports, wellness, and community. Admission is free, making it a fun stop whether you stay for an hour or the entire day.
There’s nothing quite like live music on a beautiful September evening.
đź“… Sunday, September 6, 2026
📍 Chesapeake City Park
Pack a blanket, bring a picnic, and enjoy an evening with the Virginia Symphony Orchestra under the stars. This longtime Chesapeake tradition is one of my favorite ways to slow down and enjoy the season with family and friends.
Hot chicken, hard drinks, and Music City sounds!
đź“… Saturday, September 12, 2026
🕛 12:00 PM – 10:00 PM
📍 Town Point Park | Downtown Norfolk Waterfront
Bring your boots and your appetite because NashFest 757 transforms Town Point Park into a little slice of Nashville for the day. Enjoy live country music, Nashville-style hot chicken, barbecue, whiskey tastings, craft beer, line dancing, and plenty of Southern hospitality.
Best of all, admission is free, making it a perfect way to spend a Saturday in downtown Norfolk.
One of the largest military air shows in the country returns to Virginia Beach this September—and it’s always one of the biggest weekends of the year.
📅 September 19–20, 2026
Watch incredible aerial demonstrations from the U.S. Navy Blue Angels, the F-22 Raptor Demo Team, military flyovers, parachute demonstrations, and dozens of aircraft displays. Whether you’ve attended before or it’s your first time, the Oceana Air Show is an unforgettable experience for all ages.
Calling all craft beer lovers!
đź“… Saturday, September 19, 2026 (Date subject to confirmation)
Sample beers from breweries across Coastal Virginia while enjoying local food vendors, live entertainment, and a fun atmosphere celebrating Hampton Roads’ growing craft beer scene. It’s become one of the area’s favorite fall traditions.
If you’ve lived in Hampton Roads for any length of time, you know this is one of the signature events of the year.
📅 September 25–27, 2026
The Virginia Beach Oceanfront comes alive with:
Most events are free to attend, making this one of the best family weekends of the year.
One of the year’s biggest concert events is coming to Virginia.
đź“… Saturday, September 26, 2026
Farm Aid brings together nationally recognized artists for a day of incredible music while raising awareness and support for America’s family farmers. If you’re a fan of live music and giving back to a great cause, this is one you’ll want to add to your calendar.
One of my favorite things about living here is that every season brings something different.
September still feels like summer at the beach—but with cooler evenings, community festivals, football weekends, outdoor concerts, and some of the biggest events of the year.
It’s one more reminder that when you love where you live, weekends become a little easier to fill.
Whether you’re new to Hampton Roads or you’ve called the 757 home for years, I hope you get the chance to enjoy a few of these events this month.
And if you’re thinking about making a move—whether that’s buying your first home, selling your current one, or relocating to Coastal Virginia—I’d love to help you find a place you’ll love coming home to.
See you around the 757!

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Anna
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