Festive Fly October 2025 Issue

We wanted to give a shout out to all those who recently becoming subscribers to the newsletter. We look forward to keeping you informed of all things fun going on in Virginia!

Time: October 10-12, 2025 | Place: Downtown Richmond's historic riverfront, from 2nd to 7th streets and from Byrd Street to the James River – including Brown's Island, the American Civil War Museum at Tredegar, portions of Federal Reserve parking lots, and Tredegar Street.

One of Virginia’s biggest celebrations of culture, the Richmond Folk Festival transforms downtown into a three-day party with music from every corner of the globe, delicious eats, and community vibes. With multiple stages, riverside views, and performances you won’t see anywhere else, this free festival is the crown jewel of October in Virginia.

October in Northern Virginia is bursting with fall fun 🎃. Kick things off with Vienna Oktoberfest (Oct 4), where German beer, live music, and family activities take over Historic Church Street. The following weekend, discover over 400 vendors, food, and entertainment at the Fairfax Fall Festival (Oct 11) or savor the region’s finest flavors at Taste of NoVA (Oct 11–12). Mid-month, treasure hunters will love the Lucketts Fall Vintage Market (Oct 17–19), while families can head to the Pumpkin Harvest Festival (through Oct 31) for hayrides, corn mazes, and classic autumn traditions. 🍂✨

🎨 49th Annual Fairfax Fall Festival — Sat, Oct 11 • 10:00 AM–5:00 PM, Downtown Fairfax. Over 400 art & craft vendors, food, children’s activities, beer gardens, and live entertainment.

🍷 Taste of NoVA — Oct 11-12 • 12 PM–4 PM. Northern Virginia’s top chefs & beverage experts come together for a food + wine showcase.

🍺 Vienna Oktoberfest — Oct 4 • 11 AM–7 PM, Historic Church Street, Vienna. German beer, live music, family activities, and artisan marketplace.

👕 Lucketts Fall Vintage Market — Oct 17-19 • 10 AM–5 PM (weekend). Clarke County Fairgrounds. 200+ vintage vendors, music, food trucks, and craft beer garden.

🎃 Pumpkin Harvest Festival — Oct 1–31, Great Country Farms, Bluemont, VA. Corn mazes, pumpkin patches, hayrides, rope swings, slides & more.

Central Virginia is brimming with traditions and flavors this October 🍂. Start with the State Fair of Virginia (Sept 26–Oct 5), a classic mix of rides, food, and agricultural showcases. Celebrate heritage at Fredericksburg Oktoberfest (Oct 3–5), shop local treasures at the Fall Arts & Craft Show (Oct 11–12), or catch a timeless performance of The Sound of Music running through Oct 26. Richmond comes alive too, with the soulful 2nd Street Festival (Oct 4–5), the beloved Richmond Folk Festival (Oct 10–12), and foodie favorites like Powhatan’s Festival of the Grape (Oct 4) and the Taco, Beer & Tequila Festival (Oct 18). 🎶🍇🎡
State of Virginia Fair, Time: September 26th - October 5th, Place: 13191 Dawn BLVD. Doswell, VA 23047

🇩🇪 Fredericksburg Oktoberfest — October 3-5, 2025. Traditional German food, music, dancing, polka, artisan booths and beer (and wine) variety.

🎨 Fall Arts & Craft Show — October 11-12, Fredericksburg Convention Center. Local art, jewelry, decorations, and craft vendors.

🎭 The Sound of Music (long run) — Through October 26. A musical theater production in Fredericksburg.

🎟️ Richmond Taco, Beer, Tequila Festival — Saturday, October 18, 2025, Kanawha Plaza, Richmond. (This is just across in Central VA region)

🎶 Richmond Folk Festival — October 10-12, 2025 (FREE, multiple stages, cultural music + food)

🎤 2nd Street Festival (Jackson Ward, Richmond) — October 4-5, 2025. Three stages of music, marketplace, food vendors, artists, kids’ zone.

🍇 Powhatan’s Festival of the Grape — October 4, in Historic Courthouse Village (central/near-Richmond). Wine + community festival.

Hampton Roads has something for everyone this October 🌊. Kick things off with the Historic Phoebus Fall Festival (Oct 11), a lively day of music, crafts, and food in one of Hampton’s most historic neighborhoods. Mid-month brings the Bluebird Gap Farm Fall Festival (Oct 18–19) for family fun and the Town Point Virginia Fall Wine Festival (Oct 18–19) for waterfront tastings in Norfolk, along with the Hampton Roads Philharmonic’s October Classics concert (Oct 19). Rounding out the month, enjoy art and seasonal events along the Virginia Beach boardwalk, and celebrate service families at the Military Family Festival & Resource Fair (Oct 26). 🎨🍷🎶

🐾 Bluebird Gap Farm Fall Festival — Sat & Sun, October 18 & 19, 2025, 10:00 AM–5:00 PM (Hampton). Family-friendly activities include hayrides, blacksmith demos, live entertainment, pumpkin patch, face painting, seasonal foods, games & more.

🍷 Town Point Virginia Fall Wine Festival — Saturday & Sunday, October 18–19, 2025, 11:00 AM–6:00 PM (Town Point Park, Downtown Norfolk Waterfront). Wine sampling, local wineries, shopping, and waterfront vibes.

🎨 Virginia MOCA Boardwalk Art Show & October VB Events — during October, Virginia Beach hosts fall art shows, gem & mineral shows, live music on the boardwalk, and Halloween-themed events.

🎵 Hampton Roads Philharmonic: October Classics — October 19, 2025, American Theatre (Hampton). An orchestral concert with seasonal repertoire.

🎪 Historic Phoebus Fall Festival — October 11, 2025, 10:00 AM–6:00 PM, Mellen Street in Phoebus. Crafts, music, food, community exhibits.

🎪 Military Family Festival & Resource Fair — October 26, 2025 • 12:00 PM–4:00 PM, Virginia Beach Convention Center. Fun, crafts, games, resource booths for military families. (Free for active duty)

The Shenandoah Valley is bursting with color and culture this October 🏔️🍂. The month begins with Autumnfest (Oct 4) in Woodstock, where BBQ, brews, and harness racing set the tone for fall fun. Families can soak in mountain views at the Massanutten Fall Festival (Oct 11) or browse juried art at Waynesboro’s Fall Foliage Art Festival (Oct 12–13). Later in the month, step back in time at the Heritage Festival (Oct 18) with traditional crafts and wagon rides, then close the season in Staunton with the vibrant Staunton Pride Festival (Oct 26). 🎨🎡🎭

🍂 Shenandoah Autumnfest 2025 — Sat, Oct 4 • 11:00 AM–5:00 PM, Shenandoah County Fairgrounds, Woodstock, VA. Craft brews, ciders, wines & spirits, BBQ, artisan booths, demonstrations, and harness racing.

🎡 Massanutten Fall Festival — Sat, Oct 11, 2025. Food vendors, arts & crafts, scenic chairlift rides, VR/escape room setups, and festive fall activities.

🛠️ Heritage Festival (Shenandoah Valley) — Sat, Oct 18. Hands-on history & heritage: blacksmithing, basket weaving, horse-drawn wagon rides, storytelling, and kid-friendly demonstrations.

🎭 Staunton Pride Festival — Sun, Oct 26, Gypsy Hill Park (Staunton). Live music, drag performances, local vendors & community celebration in support of Shenandoah LGBTQ Center.

🎨 Fall Foliage Art Festival — Oct 12–13 in Waynesboro. Juried art show with local artists, live music, food trucks, and fall art vibes.

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🧚🏽✨ 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.