Upcoming Summer Festivals in Winchester ☀️

Fellow Winstigators,

If you’re like me, you’ve had enough rain this week and you’re thinking about sunny weather and bright days ahead filled with fun things to do. No worries, I’ve got you covered.

I was looking at upcoming festivals and events in Winchester this summer and two caught my eye. The first was announced a couple weeks ago and I wanted to shine a light on it in case it got lost in Apple Blossom festivities:

This is a lineup of musicians that you can say you saw in Winchester after they’ve gone on to hit it big.

Taylor Hunnicutt brings a powerhouse combination of country and Southern rock, developed through years of relentless touring in dive bars and honky tonks across the country. After building a reputation for her intense, high energy shows, she dropped her debut album in late 2024. It’s an absolute banger that captures the live-energy feel from her days on the road opening for bands like the Red Clay Stays, Whitey Morgan, Joshua Ray Walker, 49 Winchester and performing at major festivals like Bonnaroo and CMA Fest.

Ben Chapman’s third full length album has been in steady rotation for me since it came out in December. It’s a great blend of funk, soul and country that hits a consistent groove throughout and ends on a great Bob Dylan cover that he sings with his girlfriend Meg McCree. If we’re lucky, maybe we’ll get them both on stage!

I can’t claim to be familiar with Micah Howard & The Southern Ghost but I like what I hear so far. 

This should be an awesome festival and it’s all for a good cause. Check out the website to learn more about Katie’s Comfort House and see if you can volunteer. Tickets are gonna sell out for this one so grab one now!

June is right around the corner and so is the Hop Blossom Craft Beer Festival. There’s going to be an awesome mix of breweries participating, everything from local favorites from right here in Winchester to great craft breweries from the rest of the region.

Hop Blossom is a fundraiser for Dakota’s Dream, a no-kill, non-profit animal rescue group. If you’re interested in helping out, check out how to volunteer for Hop Blossom. 

Pet Adoption!

Check out happy guy Andre, sassy girl Chloe, and elegant Oreo.

Events and happenings in Winchester and the surrounding territories:

Wednesday, May 14th

Stitch Needlepoint, Middleburg - Wednesday Night Stitch 5-7pm

Dirt Farm Brewing, Bluemont - American Craft Beer Week + Concord Grape Sour Release

Dividing Creek Brewing, Winchester - Disney Animated Trivia 7:30 pm

Thursday, May 15th

Bad Habits Bar and Grill, Martinsburg WV - Appalachian Noise Fest (metal festival, Thurs-Sun)

50/50 Taphouse, Winchester - 50/50 Trivia 8:30pm

Chilly Hollow Brewing, Berryville - BEER RELEASE: Fruited Sour "P.O.G. Wild", a passionfruit, orange, and guava sour, goes on tap at noon

Friday, May 16th

Bright Box Theater, Winchester - An Evening With Mike Frazier 8pm

Back Seat Events, Winchester - Colt Ford Live: Country Rock Party Night 8pm

Dirt Farm Brewing, Bluemont - Stock The Fridge Beer Sale! (20% off beer to go Fri-Sun)

Dirt Farm Brewing, Bluemont - Althouse Pottery Spring Raku Bowl Firing (Fri-Sun check for times)

Chester Street Tavern, Front Royal - Live Music: "From the Heart" John Landis, Kenny Smith, and Friends 7-10pm

Museum of the Shenandoah Valley, Winchester - Heritage Plant Sale 9am (runs through Saturday at 5pm)

Vibrissa Beer, Winchester - First Responder Friday (20% off food and beverages for all responders!) 11 am - 11pm

West Oaks Farm Market, Winchester - Farm Concert - Robbie Limon Band 7-10pm

Clarke County Fairgrounds, Berryville - Lucketts Spring Market (all weekend check for early bird times on Friday and times for Saturday & Sunday)

Saturday, May 17th

Washington County Agricultural Center, Boonsboro MD - Quad State Pickle Fest (Saturday and Sunday)

Clarke County Farmer’s Market, Berryville - 8am - noon

Locke Store, Millwood - Wine Tasting noon-3pm

Chester Street Tavern, Front Royal - Open Mic/Musician Stage noon-5pm

Hollywood Casino at Charles Town Races, Charles Town WV - Ashley McBryde 8pm

Segra Field, Leesburg - Food Truck Festival 11am-3pm

Main Street, Front Royal - 2025 Virginia Wine and Craft Festival 11am-6pm

Winchester Brew Works, Winchester - Nine Niche Ales (9th anniversary party) noon-6pm

Shenandoah Conservatory, Winchester - ShenCoLab: Festival of Arts, Ideas & Exploration 1pm (view schedule)

Handley Library, Winchester - Conservation of Historic Documents and Fine Art on Paper 10:30am

Barrel Oak Winery, Delaplane - Preakness Party 11am - 7pm

Lions Club of Charles Town, Ranson WV - Ranson Sports Card Pokémon Collectibles Memorabilia Show 9am - 3pm

Kitchen’s Farm Market, Falling Waters WV - First Annual Car Show On The Farm 10am-4pm

Lost Rhino Brewing, Ashburn - Crawfish Boil noon-5pm

Locust Post Brewery, Little Orleans, MD - Mountaineer Jeepers Go Topless Day (Jeep meetup event and trail riding) 3pm

Winchester Book Gallery, Winchester - Author Event: R. Kane Maurer - The Gallant Conqueror 11am - 1pm

Winchester Book Gallery, Winchester - Author Event: Ashley Henriott - Confidence is an Inside Job 2-4pm

Winchester Book Gallery, Winchester - Author Event: K. Ray Carter - One Innocent Comment 5-7pm

Bright Box Theater, Winchester - Phil Zuckerman’s Rock Room Concert 1:30pm

Bright Box Theater, Winchester - Stone Temple Pilots & Rage Against The Machine Tributes: Lounge Fly (STP Tribute) & Evil Empire (Rage Against The Machine) 8pm

Chilly Hollow Brewing, Berryville - Live Music: Alex Parez

Lost Barrel Brewing, Middleburg - Out West Fest 11am-5pm

Wolf Gap Vineyard, Edinburg VA - Live Music: Brennan Edwards 6-9pm

Half Note Lounge at The George Washington Hotel, Winchester - Live Music: Meisha Herron

Cedar Creek Battlefield Headquarters, Middletown - Vintage Baseball Game, Gates Open at 10 am

Sunday, May 18th

Stitch Needlepoint, Middleburg - Sunday Afternoon Stitch 2pm

Stone Branch Arts Center, Front Royal - Bookmaking Sampler Workshop

Stone Branch Arts Center, Front Royal - Bound Books Workshop

Locke Store, Millwood - Wine Tasting noon-3pm

Chilly Hollow Brewing, Berryville - EMS Week (All first responders drink 20% off -beer only- during National EMS Week from May 18 to 24 when you show your badge)

Lost Barrel Brewing, Middleburg - Distinguished Gentleman’s Ride (vintage motorcycle fundraiser) 12:30-4:30pm

Monday, May 19th

The Catamount Lounge, Front Royal - Open Mic Monday, 7-10p

Tuesday, May 20th

Vibrissa Beer, Front Royal - Trivia Night 6:30pm

Dirt Farm Brewing, Bluemont - Happy Hour 3-5pm half price pints!

Wolf Gap Vineyard, Edinburg VA - Behind The Scenes Tour With The Owner 2-3:30pm

Like this email? Forward to a friend and tell them to subscribe.

Follow us on Instagram.

Questions, comments, suggestions or just want to say hi? Send us a note at [email protected]

Have fun out there!