Welcome to your 1st Festive Flight!

If you enjoy discovering cools things on the weekdays, weekends, off-time, anytime we are for you. Sit back in your chair and get your scroll down to find out the month of September events!

Enjoy the boardwalk and waves of Fun!

Time: September 26-28, 2025 | Place 1st-35th Street, Virginia Beach Oceanfront

Virginia Beach turns into pure seaside magic as Neptune Festival takes over the boardwalk! 🎶 Two stages of live music, 200+ artists and vendors, and world-class sandcastles make for a weekend packed with art, food, and oceanfront fun. A Hampton Roads tradition not to miss. 🎉

Alexandria Old Town Art Festival, Time: September 13-14, Place: 300 John Carlyle Alexandria, VA, Admission is free!

🎨✨ Art takes over King Street! The Alexandria Old Town Art Festival brings thousands of handmade works — from sculpture to jewelry — all crafted by local and national fine artists. Recently ranked among the nation’s top art festivals, it’s a DMV must-see for art lovers. 🖼️🌟

Richmond Fall Growers & Night Markets, Time: September 13 & 20, Place: Legend Brewing Co. at 321 West 7th St Richmond VA 23224 (Fall Growers) and 100 N 17th St, Richmond, VA 23219 (Night Markets)

*🌱✨Manchester’s Southside has a new Saturday ritual — fresh produce, baked goods, and locally made bites at Legend Brewing Co. from May through October. With yoga at sunrise, a kids club with storytime and crafts, and 20+ vendors each week, the market blends food access with community spirit. Born from a food justice mission, it’s more than shopping — it’s a Southside gathering place for neighbors to feed body, soul, and family. 💚

State of Virginia Fair, Time: September 26th - October 5th, Place: 13191 Dawn BLVD. Doswell, VA 23047

🎡✨From thrill rides to blue-ribbon livestock, the State Fair brings classic fair magic to Doswell every fall. Expect concerts, fried delights, agricultural showcases, and family fun stretching across the Meadow Event Park. Whether you come for the rides, the food, or the farm charm, this fair is Virginia tradition at its finest. 🌟

Thrift World (Vintage Pop-Up Shopping Event), Time: September 13th 10am-5pm Place: Fredericksburg Convention Center, 2371 Carl D Silver Pkwy Fredericksburg, VA

Thrift World Expo is a fun shopping experience unlike any other! Our curated vendors provide a wide selection of vintage clothing, jewelry, records, live tattooing, piercings, gourmet snacks, a full bar and more.

Harambee 360 Black Arts Festival (50th Anniversary), September 26-28 Fredericksburg Area Museum, 907 Princess Anne St, Fredericksburg, VA

🎭✨Now in its 50th year, Harambee 360 celebrates Black culture and creativity with a weekend of music, dance, art, and community in Fredericksburg. From live performances to vibrant showcases of local talent, this milestone festival is both a tribute to tradition and a stage for the next generation. A cultural heartbeat moment you won’t want to miss. 🖤🎶

Fredericksburg Greek Festival
Time: September 27th (11am-8pm) - 28th (12pm-4pm)
Place: Nativity of the Theotokos Greek Orthodox Church Spotsylvania, VA

🇬🇷✨ The Fredericksburg Greek Festival fires up the grill with marinated meats, savory pastries, and sweet treats made from beloved parish recipes. Pair your favorites with Greek wine, coffee, or ouzo, then stroll a marketplace of handmade jewelry, glassware, and imported olives and oils. A community tradition where food, culture, and giving back come together. 💙🍇

NAS Oceana Airshow, Time: September 20-21st
Place: 1750 Tomcat Blvd, Virginia Beach, VA

✈️✨ The sky comes alive over Virginia Beach as the NAS Oceana Airshow returns with the U.S. Navy Blue Angels, daring parachute teams, and gravity-defying aerial stunts. One of the East Coast’s premier aviation spectacles, it’s a family-friendly weekend of jet noise, food, and pure adrenaline.

NASHFEST 757, Time: September 13, 2025, Time: Noon - 10PM
Place: Norfolk Waterfront, Free & Open to the Public

🎸🔥 Norfolk’s waterfront gets a Nashville makeover with hot chicken, whiskey tastings, and a full lineup of country music. Add line dancing, craft beer, and a coastal breeze, and you’ve got Hampton Roads’ honky-tonk block party.

Phoebus Jazz Festival, Time: September 19-21st, Place: Hampton Phoebus District

🎷🌙 Hampton’s historic Phoebus district transforms into a three-day celebration of jazz, blending soulful sets from regional artists with performances by national headliners. Grab a seat, sip something local, and let the music roll through the streets.

Smith Mountain Lake Wine Festival, Time September 27-28, Place Bernard’s Landing Smith Mountain Lake 775 Ashmeade Road Moneta, VA

🍷🍂 Sip and savor lakeside as Virginia wineries, food vendors, and live bands gather for a scenic fall tradition. With mountain views, great pours, and plenty of local flavor, it’s the perfect I-81 escape.

Queen City Mischief & Magic
Time September 27 (1pm - 9:30pm), 28 (7am - 10pm) and 29 (9am - 4pm)
Place: Downtown Staunton, VA

🪄🏰 Staunton’s streets turn whimsical with a weekend of fantasy, cosplay, and magical fun. From wizard-themed markets to street performers and live shows, it’s small-town charm wrapped in big imagination.

🧚🏽✨ This email was brought to you by the Festive Fairy of FestiveFly.

🍴✨ At FestiveFly, we spotlight Virginia’s festivals, fairs, and cultural gatherings — and through our partner platform Trukfoo, we make it easy to find the food trucks, vendors, and local flavors that bring these events to life. Together, we’re building a community hub where discovery meets fellowship — helping neighbors connect over food, music, and fun while supporting the small businesses and creatives who fuel Virginia’s culture.