Festivals near Sperryville, VA.

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 ....

Fall Fest at Camp Horizons

• Oct. 26 - Oct 26, 2025
• Camp Horizons - Harrisonburg, VA USA

Celebrate the season at Camp Horizons’ Fall Festival—an autumn afternoon packed with fun for all ages! This free community event features fall-themed ....

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 ....

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 ....

PWCFRS 2nd Annual Public Safety Fall Expo

• Oct. 4 - Oct 4, 2025
• PWC Stadium Complex - Woodbridge, VA USA

• Community (Community / Social)
• Community (Family & Kids)
• Community (Local / Fair)
• Music
• Seasonal (Fall)

• FREE!!

The Public Safety Fall Expo will bring together a wide range of public safety agencies and organizations from across Prince William County and the sur ....

A Day of Sips on National Coffee Day – Cafely

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

• Food / Wine / Beer

• FREE!!

Hey there, coffee lovers! Have you ever stopped to think about just how much a simple cup of coffee means to so many of us? As we gear up to celebrate ....

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 ....

2025 Via Colori® Stafford Street Art Festival

• Sep. 28 - Sep 28, 2025
• STAFFORD REGIONAL AIRPORT - Fredericksburg, VA USA

What: 5th Annual Via Colori® Stafford Street Art Festival When: Saturday, September 27 - Sunday, September 28, 10:00-5:00 both days* Where: Stafford R ....

Via Colori® Stafford Street Painting Festival

• Sep. 28 - Sep 28, 2025
• STAFFORD REGIONAL AIRPORT - Fredericksburg, VA USA

5th Annual Via Colori® Stafford Street Art Festival At this free, family-friendly event, watch 70+ local artists create large-scale street paintings w ....

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 ....

2025 Via Colori® Stafford Street Art Festival

• Sep. 27 - Sep 27, 2025
• STAFFORD REGIONAL AIRPORT - Fredericksburg, VA USA

What: 5th Annual Via Colori® Stafford Street Art Festival When: Saturday, September 27 - Sunday, September 28, 10:00-5:00 both days* Where: Stafford R ....

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 ....

Via Colori® Stafford Street Painting Festival

• Sep. 27 - Sep 27, 2025
• STAFFORD REGIONAL AIRPORT - Fredericksburg, VA USA

5th Annual Via Colori® Stafford Street Art Festival At this free, family-friendly event, watch 70+ local artists create large-scale street paintings w ....