Festivals near Winchester, VA.

??Thursday Night Trivia (7-9 PM) With Rockstar DJ

• Nov. 20 - Nov 20, 2025
• Heroic Axe - Warrenton, VA USA

Rally your crew for a shot at the Champion’s Trivia Belt ??! Reservations & ?? Throwing Never Required ?? Minutes from Haymarket, Gainesville, & Warr ....

Live Music by Sharif

• Nov. 16 - Nov 16, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

Live Music by Shade Tree Collective

• Nov. 15 - Nov 15, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

Wayne Snow

• Nov. 15 - Nov 15, 2025
• Two Twisted Posts Winery \u0026 Tavern - Purcellville, VA USA

• Music

Join us for a relaxing afternoon of live music featuring Wayne Snow on acoustic guitar. Come enjoy great music, good company, and a glass or two of yo ....

DMV Chocolate and Coffee Festival

• Nov. 15 - Nov 16, 2025
• Dulles Expo Center - Chantilly, VA USA

• $10 - $25
• $25 - $50

Come take a journey with your senses. Sip coffees from around the world, brought to you by local vendors. Taste chocolates of every form for every pal ....

Live Music by Dill Pickers

• Nov. 14 - Nov 14, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

??Thursday Night Trivia (7-9 PM) With Rockstar DJ

• Nov. 13 - Nov 13, 2025
• Heroic Axe - Warrenton, VA USA

Rally your crew for a shot at the Champion’s Trivia Belt ??! Reservations & ?? Throwing Never Required ?? Minutes from Haymarket, Gainesville, & Warr ....

Cheesin' for a Reason - a grilled cheese & tomato soup extravaganza, presented by WATTS

• Nov. 8 - Nov 8, 2025
• Old Town Winchester - Winchester, VA USA

• $1 - $10
• $10 - $25

The festival event that is sweeping the nation is coming to downtown Winchester! Join WATTS in Cheesin' for a Reason - our first annual grilled cheese ....

McCoy's Grand FallFest Open House

• Oct. 25 - Oct 25, 2025
• McCoy Grand Theatre and Museum - Moorefield, WV USA

FALLFEST OPEN HOUSE will feature 12 bands on both the Mainstage and Courtyard Plaza Stage along with Museum Tours, Broadway Bingo, a Corn Hole Tournam ....

?? The Big Dill at Devil’s Due ??

• Oct. 25 - Oct 25, 2025
• 315 James Burr Blvd - Kearneysville, WV USA

?? The Big Dill at Devil’s Due ?? Saturday, October 25, 2025 | 11AM – 5PM Devil’s Due Distillery – 315 James Burr Blvd.; Kearneysville, WV It’s one he ....

Hampshire County Fall Crawl

• Oct. 18 - Oct 18, 2025
• 22580 Northwestern Turnpike - Romney, WV USA

• Other / General

This self-guided tour is your chance to explore local farms, businesses, and artisan vendors, all while enjoying the crisp autumn air and stunning sce ....

50th Annual Apple Butter Festival

• Oct. 10 - Oct 12, 2025
• Berkeley Springs State Park - Berkeley Springs, WV USA

??? The 50th Annual Apple Butter Festival is almost here — and this year is going to be legendary! ??? Join us October 10–12, 2025 in beautiful downt ....

Reynolds Memorial Baptist Church's 100 Year Anniversary Celebration

• Oct. 4 - Oct 4, 2025
• 3748 Sperryville Pike - Sperryville, VA USA

• Music

This free event will begin at 4:00 PM. There will be a country gospel band, BBQ, a variety of side dishes and desserts, plus games and a cake walk. ....

DTFEST 2025

• Oct. 4 - Oct 4, 2025
• One Loudoun - Ashburn, VA USA

• $10 - $25

Celebrate the Spirit of Dashain and Tihar — Nepali Style! DTFEST 2025 is back — and it’s bigger, brighter, and more vibrant than ever before! Now in ....

Great Falls Oktoberfest

• Oct. 3 - Oct 3, 2025
• Great Falls Grange - Great Falls, VA USA

• $50 - $100

This event will be advance tickets only. ....

Cafely’s Midday Brew

• Sep. 29 - Sep 29, 2025
• Cafely - Reston, VA USA

• Nightlife

• FREE!!

Hey there, coffee lovers! We’re buzzing with excitement as National Coffee Day rolls around on September 29, a day to raise our mugs to the brew that ....

Cafely's Roast of the Day: National Coffee Day

• Sep. 29 - Sep 29, 2025
• Cafely - Hancock, MD USA

• Nightlife

• FREE!!

Get ready to raise a mug to National Coffee Day on September 29, a day that celebrates the beloved brew uniting people across the United States and be ....

Distinguised Gentelmans RDrive

• Sep. 28 - Sep 28, 2025
• Lost Barrel Brewing - Middleburg, VA USA

An on-road motoring fundraising event, uniting classic cars built 40 years or older, encouraging drivers and passengers around the world to dress dapp ....

Super Trans AM – The Ultimate ‘70s Rock Experience - September 27 - Tarara

• Sep. 27 - Sep 27, 2025
• Tarara Summer Concert Series - Leesburg, VA USA

• Music

• $10 - $25

???? Super Trans AM – The Ultimate ‘70s Rock Experience LIVE at Tarara! ???? Buckle up, because Super Trans AM is taking you on a high-octane ride th ....

Live Music by Steve Boyd & Friends

• Sep. 27 - Sep 27, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....

Lost Barrel Brewing Oktoberfest 2025

• Sep. 27 - Sep 27, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• $25 - $50

??? TICKETS: Presale (Ends 9/8 at 10PM): $30 – Includes souvenir glass + seven (7oz) tasting tickets General (Ends 9/26 at 10PM): $35 – Includes souve ....

Mercy Fest

• Sep. 27 - Sep 27, 2025
• Historic District - Manassas, VA USA

• $1 - $10
• $10 - $25

Join us on September 27th for Mercy Fest 2025, House of Mercy's annual fundraiser dedicated to making a difference in the lives of those in our commun ....

2nd Annual Rokeby Community Fall Festival

• Sep. 27 - Sep 27, 2025
• Oak Spring Garden Foundation - Upperville, USA

• FREE!!
• $1 - $10

The Rokeby Farm property has a long and storied history as an icon of the Virginia Piedmont. Operated today by the Oak Spring Garden Foundation, Rokeb ....

Old Town After Hours

• Sep. 26 - Sep 26, 2025
• Main Street - Warrenton, VA USA

• Music

Live music on Main Street, Fridays 6-9 pm ....

Live Music by Brett Baboorian

• Sep. 26 - Sep 26, 2025
• Lost Barrel Brewing - Middleburg, VA USA

• Music

Lost Barrel Brewing is an all ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy our taproom, porch, stunning yard or pri ....