Weekend in Virginia: Highlights by Region
🏛️ DMV / DC-Area
🇬🇷 St. Theodore Greek Festival (DMV) — Sept 26-28 • Fri & Sat 11 AM - 9 PM, Sun noon-7 PM. Delicious Greek eats, culture, live music & crafts in the DMV.
🎶 Candlelight Concert Series — Sept 26. A candlelit evening in DC featuring classical and crossover hits performed by string ensembles.
🎭 Shakespeare Theatre Company – Merry Wives — Ongoing through Sept 28, downtown DC. Catch one of the nation’s top Shakespeare productions in an intimate setting.
🎪 Cirque du Soleil: LUZIA (Tysons, VA) — Sept 26–28. A dazzling, dreamlike show blending circus arts and Mexican culture.
🎨 Richmond / Central VA
🌱 Richmond VegFest — Sept 28, Byrd Park (Richmond). Vegan-friendly vendors, foodies, families, community vibes.
🏳️🌈 VA PrideFest 2025 — Sept 27, Midtown Green (Richmond). Celebrate LGBTQ+ culture with music, drag, and food.
🎡 State Fair of Virginia (Doswell) — Sept 26-Oct 5. Classic fair fun — rides, food, livestock, contests, live music.
🌊 Hampton Roads / Coastal VA
🌊 51st Annual Neptune Festival Boardwalk Weekend — Sept 26–28, Virginia Beach Boardwalk. The grand finale of summer with live concerts, an art & craft show, sand sculptures, food vendors, parades, and an 8K race — stretching 33 blocks along the oceanfront.
⚓ 99th Annual Hampton Cup Regatta — Sept 27–28, Fort Monroe. High-speed hydroplane boat races roar across the water in one of the oldest racing traditions in the U.S.
👻 Haunted Screams Expo — Sept 27–28, Hampton Convention Center. A spooky weekend of horror vendors, costume contests, movie screenings, and celebrity guests.
🏔️ Shenandoah Valley
🎨 Art in the Park: Scenes from Shenandoah — Sept 26–27, Big Meadows Wayside (mile 51.2, Skyline Drive). Free art demos + workshops in watercolor, printmaking, fiber, and mixed media.
🌌 Night Skies in Shenandoah National Park — Fri, Sept 26 • 6:45 PM–12:30 AM, Big Meadows (mile 51). Stargazing + astronomy presentations under one of Virginia’s clearest skies.
🪄 Queen City Mischief & Magic — Sept 27–28, Downtown Staunton. A weekend of fantasy, cosplay, street performers, and family-friendly magical fun.
🧵 Shenandoah Valley Fiber Festival — Sept 27–28, Clarke County Ruritan Fairgrounds. Vendors, workshops, and hands-on crafts celebrating fiber arts. ($5 admission)
🖼️ MSV at Night (Museum of the Shenandoah Valley) — Fri, Sept 26 • 5–8 PM, Winchester. After-hours art + music featuring Lua Project, artisan market, and Frida Kahlo photo exhibit.
🎸 Southwest VA Spotlight
🌲 Woodbooger Festival (Norton, VA) — Live music, food, craft vendors, contests, guided hikes & rides, canoe rides, 5K trail race, Bigfoot expert presentations, kids’ activities, and more.
🎉 Vintage in the Valley Antiques & Arts Festival (Chilhowie, VA) — Saturday, Sept 27 • 10:00 AM–6:00 PM. Antiques & vintage vendors line the streets of Downtown Chilhowie, accompanied by local bluegrass performances.
✨ Virginia comes alive this weekend — from sand sculptures 🌊 at the Neptune Festival to rainbow celebrations 🏳️🌈 at PrideFest, from fried treats 🎡 at the State Fair to spooky thrills 👻 in Hampton. Wherever you roam, may your Pull Up be full of food, fellowship, and fun.
🧚🏽✨ FestiveFly is your guide to Virginia’s festivals, fairs, and cultural gems — led by the Festive Fairy, our playful spirit of discovery, who reminds us to celebrate local and find joy in community. Together with Trukfoo, the platform connecting food trucks and foodies, FestiveFly is part of a growing ecosystem built to make it easier to pull up, eat well, and experience more. Don’t miss out — sign up for our emails and let the Festive Fairy deliver the best of food, fellowship, and fun straight to your inbox.