Festivals near Shepherdstown, WV.

Thurmont Main Street Art and Wine Stroll Preakness Night

• May. 15 - May 15, 2026
• Thurmont Main Street - Thurmont, MD USA

• Food / Wine / Beer

Join us for Northern Frederick County’s best party at our Main Street Art & Wine Stroll. Wow! Do we have a lineup for you for our Summer Thurmont Main ....

Asian Festival on Main

• May. 17 - May 17, 2026
• Fairfax Old Town Square Park - Fairfax, VA USA

• Other / General

Asian Festival on Main is a free, one-day outdoor family festival in Historic Old Town Fairfax City celebrating Asian food, culture, and community. E ....

Asian Festival on Main

• May. 17 - May 17, 2026
• 10415 North St - Fairfax, VA USA

• Other / General

Asian Festival on Main is a free, one-day outdoor family festival in Historic Old Town Fairfax City celebrating Asian food, culture, and community. E ....

Thursday May 21st with Michael Groves at Orlean Market & Pub

• May. 21 - May 21, 2026
• Orlean Market \u0026 Pub - Marshall, VA USA

Everyone is welcome—whether you want to showcase your talent, participate, or just enjoy the performances! Before or during the show, treat yourself ....

Wardensville Spring Fest

• May. 23 - May 23, 2026
• Wardensville - Wardensville, WV USA

• Other / General

Shake off winter and make a day of it in Wardensville, WV! Spring Fest brings together everything we love about this town—good food, live music, creat ....

Asia on the Creek

• May. 23 - May 23, 2026
• Carroll Creek Outdoor Amphitheater - Frederick, MD USA

• Music

Come join us at the Carroll Creek Outdoor Amphitheater for a day filled with vibrant cultural performances, delicious Asian cuisine, and exciting acti ....

NoVA MusicFest at 868 Estate Vineyards

• May. 24 - May 24, 2026
• 14001 Harpers Ferry Rd - Purcellville, VA USA

• Music

• $25 - $50

Get ready for the ultimate Sunday Funday! On Sunday, May 24, NoVA MusicFest returns to the rolling hills of 868 Estate Vineyards for our sixth year of ....

Bull Run Wine Festival Spring 2026

• May. 30 - May 31, 2026
• The Winery at Bull Run - Centreville, VA USA

• Food / Wine / Beer

• $25 - $50

Join your friends for an exciting wine festival hosted by The Winery at Bull Run! With your ticket, enjoy complimentary wine tastings from Virginia's ....

*POSTPONED* Inaugural Four Nations Cup Polo Tournament Feat. US x Pakistan x India x UK

• May. 31 - May 31, 2026
• Great Meadow - The Plains, VA USA

• Community (Fundraiser)

• $250+

AFTER CAREFUL CONSULTATION AND CONSIDERATION OF THE CURRENT POLITICAL CLIMATE, PARTICULARLY THE RENEWED TENSIONS BETWEEN INDIA AND PAKISTAN, WE HAVE M ....

Cafely's Impactful New Beanwave Dashboard is Here

• Jun. 6 - Jun 6, 2026
• Cafely - Gettysburg, PA USA

• Food / Wine / Beer

• FREE!!

Embark on a journey with Cafely to uncover the latest Starbucks statistics and delve into the pivotal trends shaping the ever-evolving coffee industry ....

2026 WESTERN MARYLAND BLUES FEST

• Jun. 6 - Jun 7, 2026
• Hub City Brewery - Hagerstown, MD USA

• Music

• $50 - $100

We're excited to announce the return of the largest blues music festival in western Maryland to downtown Hagerstown. June 6 & 7, 2026 We're stoked to ....

Loudoun Appalachian Trail Festival

• Jun. 6 - Jun 6, 2026
• Hillsboro Old Stone School - Hillsboro, VA USA

• Arts (Arts & Crafts)
• Community (Community / Social)
• Food / Wine / Beer
• Music
• Outdoor / Recreation

• FREE!!

Celebrate the spirit of the great outdoors at the Loudoun Appalachian Trail Festival on June 6th, in historic Hillsboro, Virginia. This free ....

Cajun Festival 2026

• Jun. 13 - Jun 13, 2026
• Breaux Vineyards - Purcellville, VA USA

• Other / General

• $10 - $25

Your favorite LoCo Cajun Cousins are at it again!! Come celebrate New Orleans and Cajun heritage with your Breaux ‘krewe’ on this day of fun for the ....

Cacapon Riverfest

• Jun. 19 - Jun 19, 2026
• 24 Rickie Davy Ln - Capon Bridge, WV USA

• Other / General

This year, the event will be held on Friday, June 19, 2026 and Saturday, June 20, 2026 at The River House. You can meet fellow river-lovers, attend e ....

Community Picnic & Benefit Motorcycle Ride & Show – Augusta, WV

• Jun. 20 - Jun 20, 2026
• Central Hampshire Park - Augusta, WV USA

• Other / General

Join the North River Ruritan Club for a Community Picnic and Benefit Motorcycle Ride & Show on Saturday, June 20, 2026 at Central Hampshire Park in Au ....

Contemporary American Theater Festival

• Jul. 10 - Aug 2, 2026
• Shepherd University - Shepherdstown, WV USA

• Other / General

• $25 - $50
• $50 - $100

The Contemporary American Theater Festival (CATF) announces its 2026 season, featuring five new plays by award-winning playwrights that include four w ....

Key West Festival

• Jul. 11 - Jul 11, 2026
• Breaux Vineyards - Purcellville, VA USA

• Other / General

• $10 - $25

Soak up the summer sun while dancing to live music and enjoying great wine! LIVE MUSIC LINE-UP 11:30 am – 2:30 pm – KEN WENZEL 3:00 – 6:00 pm – TRO ....

Eli Lev (folk pop musician) at Old Bust Head Brewing Company

• Jul. 31 - Jul 31, 2026
• Old Bust Head Brewing Company - New Baltimore, VA USA

• Music

Rising singer-songwriter Eli Lev is making the world a smaller place, one song at a time. Eli pens lyrics and melodies for everyday enlightenment—song ....

Eli Lev (folk musician) performing at Old Bust Head Brewing Company

• Jul. 31 - Jul 31, 2026
• Old Bust Head Brewing Company - New Baltimore, VA USA

• Music

Rising singer-songwriter Eli Lev is making the world a smaller place, one song at a time. Eli pens lyrics and melodies for everyday enlightenment—song ....

World Heritage Festival @ Carroll Creek Park, Frederick, MD

• Oct. 10 - Oct 10, 2026
• Carroll Creek Park - Frederick, MD USA

• Other / General

Join us in beautiful Carroll Creek Linear Park for the Frederick World Heritage Festival, a vibrant celebration of global cultures, traditions, and co ....

DMV Chocolate and Coffee Festival

• Nov. 14 - Nov 15, 2026
• Dulles Town Center - Dulles Town Center, VA USA

• Other / General

• $10 - $25

Sip, Sample, and Shop! Indulge your senses at the DMV Chocolate and Coffee Festival—the premier gathering for coffee lovers, chocolate enthusiasts, an ....

North River Mills/Ice Mt. Festival 2026

• May. 9 - May 9, 2026
• 8200 Cold Stream Rd - Capon Bridge, WV USA

• Other / General

Enjoy a relaxing day in this once-bustling town. In the early 1980's we had our own post office, gas station, and general merchandise store. Granville ....

Make it a Family Weekend at Maaden LIV Golf Virginia!

• May. 7 - May 10, 2026
• Trump National Golf Club Washington DC - Sterling, VA USA

• $25 - $50

Thursday, May 7 – Sunday, May 10 Gates open at 11:00 a.m. Thursday, 10:00 a.m. Friday, 11:00 a.m. Saturday, and 10:00 a.m. Sunday Bring the whole cr ....

Festival Of Colors

• May. 3 - May 3, 2026
• Bull Run Park - Centreville, VA USA

• Other / General

• $10 - $25

?? When: Sunday, May 3 | 12:00 PM – 7:00 PM ?? Where: Bullrun Park, Centerville, VA What to Expect: Dance, play, shop, eat, throw colors on people, a ....

Lebanese Wine Pairing Dinner at Byblos Gainesville

• Apr. 26 - Apr 26, 2026
• Byblos Restaurant - Gainesville, VA USA

• $50 - $100

Join Byblos owner Walid and WSET-Certified wine expert Bob for an evening where Lebanese culinary heritage meets the sophistication of fine wine. Each ....