Weekend in Virginia: Highlights by Region

🏛️ DMV / DC-Area

  • 🍷 Fall Wine Festival & Sunset Tour — Oct 10–12, 6 PM–9 PM, Fairfax. Taste unlimited samples from Virginia’s finest wineries under evening skies.

  • 😂 Because They’re Funny DC Comedy Festival — Oct 10–12 along The Wharf, Washington, DC. A multicultural comedy fest with stand-up, films, live acts.

  • 🦇 DC WitchFest 2025 — Sat, Oct 11 • 11 AM–4 PM, The Coupe, Washington, DC. Witchy crafts, tarot, astrology, live portraits, family-friendly and free.

  • 🍻 Snallygaster 2025 — Sat, Oct 11. D.C.’s big beer festival, over 450 craft beers, food trucks, live music.

  • 🥂 Taste of the Harvest / Harvest event at THEARC — Sat, Oct 11 • 2 PM–8 PM, THEARC Farms, SE DC. Urban farm tastings, dine-with-your-neighbors, free but RSVP required. Building Bridges Across The River

🚂 Fredericksburg / Central VA

  • 🍁 Braehead Farm Fall Festival Weekends — Saturdays & Sundays through October 26 • 9:00 AM–6:00 PM. Hayrides, pumpkin patches, corn maze & family fun.

  • 🎨 Fall Arts & Craft Show — Oct 11–12, 2025, at Fredericksburg Convention Center. Local artists, jewelry, décor & handcrafted goods.

🎨 Richmond

🌊 Hampton Roads / Coastal VA

  • 🎨 Virginia MOCA Boardwalk Art Show — Oct 10–12, Virginia Beach Boardwalk (24th to 35th Street). Features 150+ artists, live performances, theater, and the Liquid Art Beer Garden.

  • 🎪 Fil Fest USA — Oct 10–12, Rudee Loop, Virginia Beach. Culture, food, and Filipino heritage events by the waterfront.

  • 🛍️ Downtown Hampton “Flea Market After Dark” — Saturday, Oct 11 • 5:00 PM–10:00 PM, East Queen Street. Outdoor dining, music, and gathering under the evening sky.

🏔️ Shenandoah Valley

  • 🏔️ Massanutten Fall Festival — Oct 11, 2025 (Saturday). Includes food vendors, arts & crafts, scenic chairlift rides, kids’ activities, and more. Massanutten Resort

  • 🎨 Autumnfest Vendor Showcase — Oct 4 • 11:00 AM–5:00 PM, Shenandoah County Fairgrounds, Woodstock. A bit earlier than your window, but it’s a strong local fall anchor.

  • 🏛️ MSV Community Celebration (LGBTQ+ Day at MSV) — Saturday, Oct 11 • 10 AM–5 PM. Free event with music, drag shows, vendors, and community presentations at the Museum of the Shenandoah Valley.

🍂 Virginia is buzzing this weekend — from comedy and craft beer on D.C.’s waterfront 🍻 to soulful melodies along Richmond’s riverfront 🎶. Fredericksburg keeps it cozy with pumpkins, crafts, and family fun 🚂, while Hampton Roads turns up the coastal charm with art, culture, and lights by the sea 🌊. In the valley, Massanutten’s fall celebration and Winchester’s community day bring mountain color and hometown pride 🏔️. Whether you’re sipping, strolling, or dancing, there’s a festival for every flavor. So go on pull up, explore, and let your weekend taste like Virginia.

Festive Fairy of Festive Fly and Tuko of Trukfoo

Hungry for more than just updates? With Trukfoo, you’ll know exactly where your favorite food trucks are rolling, what they’re serving, and how to be first in line. 🚚💨 From tacos to treats, Tuko and the Festive Fairy make sure you never miss the flavor, fellowship, and fun. We are now onboarding foodies and food trucks! Join the movement today by signing for the Trukfoo app and let your weekends taste better. 🍔

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

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.




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