Festivals near Shepherdstown, WV.

Live Music by Steve Boyd & Friends

• Nov. 22 - Nov 22, 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 ....

2000s Night

• Nov. 21 - Nov 21, 2025
• Lost Barrel Brewing - Middleburg, VA USA

We’re throwing it back to the era of flip phones, low-rise jeans, boy bands and girl groups—get ready for 2000s Night at Lost Barrel Brewing! What to ....

??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 ....

?? 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 ....