Pints 🍻 Paws 🐾 & Plans 📅 – Your Weekend In Winchester.

Winstigators,

Wanted to take a quick second to share a rundown of my visit to Chilly Hollow Brewing in Berryville last week. My wife and I met up with some friends on Friday afternoon and had a great time.

The brews were on point—I especially liked the P.O.G. (passionfruit, orange, and guava) sour ale, which was perfect for a scorching hot afternoon. My wife’s Black Widow pour, a German dark beer, was smooth and flavorful—definitely one I plan to enjoy this fall on a return trip. And for the designated drivers or anyone just looking for something non-alcoholic, the slushies were a hit—blue raspberry lemonade was my favorite.

Did I mention walking tacos? Chili, cheese, lettuce, sour cream, salsa, and guacamole piled on Fritos (or Doritos, if that’s your thing) in a bag. Is it gourmet? Nope. Is it perfect for enjoying beers with friends to kick off the weekend? Absolutely.

Chilly Hollow is also super kid-friendly. My son’s chicken nuggets and mac & cheese were a hit, and the expansive playground kept him busy while we relaxed.

I can’t recommend this place enough. Looking forward to going back soon to try more brews!

Justin Clyde Williams at Bright Box Friday Night!

Last week, I also had the pleasure of seeing Justin Clyde Williams open for Silverada in D.C. If you're into heartfelt lyrics full of heartbreak and regret—immediately followed by a song that'll make you laugh out loud—don’t miss the chance to catch him live. He’ll be at Bright Box Theater this Friday night. Go check him out!

Pet Adoption!

Check out happy Bluey, smart-guy Aiden, ready-to-go Buck, and understanding Binx.

Events and happenings in Winchester and the surrounding territories:

Wednesday, July 30th 

Clarke County Parks and Recreation, Berryville - FREE Summer Concert Series: Concert #3 Robbie Limon, 6pm

The Virginia Piedmont Heritage Area Association, Middleburg - The Heritage Area in the American War for Independence, 5:30 pm

Clarke County Virginia Rotary Club, Berryville - Rotary Evening Social At Chilly Hollow Brewing, 6pm

Mt. Defiance Cidery and Distillery, Middleburg - Bingo Night, 6pm

Touch of Texas, Bunker Hill - Free Line Dancing Lessons, 7pm

Skyline Sports Bar, Front Royal - Open Mic @ Skyline Sports Bar (hosted by CBD), 7pm

Strasburg Community Library, Strasburg - End of Summer Reading Ice Cream Party, 1pm

Broken Window Brewing Co., Winchester - Championship Trivia, 7pm

Shenandoah Valley Axe Throwing Co, Front Royal - Music Bingo & Trivia Night Every Wednesday, 6pm

Thursday, July 31st

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

Bright Box Theater, Winchester - Joey Harkum (Solo), 7pm

The Farm Brewery at Broad Run, Haymarket - Movies On The Farm, 7pm

On Cue Sports Bar & Grill, Front Royal - Karaoke Night @ On Cue, 7:30 pm

Brickhouse Bar & Grill, Front Royal - Brickhouse Bar & Grill - Mack Berry, 4pm

Runners’ Retreat, Winchester - RRTGR (running club) - Thursday, 6pm

Wildlife Center of Virginia, Front Royal - Summer Library Tour - Samuels Public Library, 2pm

Jordan & Hess Company, Martinsburg - Annual Summer Sidewalk Sale, 9am

Samuels Public Library, Front Royal - Studio 330: Embroidery Club, 10am

A Grave MisBake, Stephenson - Pop Up Bake Sale, 12pm

The Homestead Farm at Fruit Hill Orchard, Winchester - Bluegrass on the Farm, 6pm

Tilty McFlipperz, Martinsburg - Tilty McFlipperz Amateur Pinball Tournament, 7pm

Apollo Civic Theatre, Martinsburg - AUDITON CALL: RUMORS, 6pm

Cousins Maine Lobster, Purcellville - Cousins Maine Lobster🦞at Costello's Ace Hardware of Purcellville, 10am

Lost Barrel Brewing, Middleburg - Double Hard Seltzer Release: Strawberry Lemonade & Piña Colada, 12pm

Wild Hare Cider Tasting Room, Berryville - Tiered Happy Hour & Game Night @ The Tasting Room, 5pm

Willowsford Conservancy & Farm, Aldie - Willowsford Farm Stand at the Boat House, 4pm

Chilly Hollow Brewing Company, Berryville - Bingo Night @ Chilly Hollow Brewing, 6:30 pm

Friday, August 1st

Shenandoah County Library, Edinburg - Finale Magic Show, 7pm

Wolf Gap Vineyard, Edinburg - First Friday! Food Specials & Live Music with The MotherTuckers, 6-9pm

Middleburg VA - 19th Annual Summer Sidewalk Sale (multiple dates)

West Oaks Farm Market, Winchester - Smuggler’s Moon, live music 6-9pm

Flying Ace Farm, Lovettsville - Live Music by Noah "Red" Hawes at Flying Ace Farm, 6pm

Monks BBQ, Purcellville - Sidetracked at Monk's BBQ, 8pm

Brickhouse Bar & Grill, Front Royal - Dj Robbie and Rockstar Karaoke, 8pm

Touch of Texas, Bunker Hill - Ladies Night, 8pm

The Vintage Barrel, Luray - It's Trivia Night at The Vintage Barrel (in Luray, VA)!, 7pm

Shenandoah River State Park, Bentonville - Toads, Turtles & Snakes, 11am

Dirt Farm Brewing, Bluemont - American Craft Beer Month - Weekly Beer Releases at Dirt Farm, 12pm

Jordan River Theatre Company, Front Royal - Jordan River Theatre Company presents Rodgers and Hammerstein's State Fair, 6:30 pm

Apollo Civic Theatre, Martinsburg - Audition call: Rocky Horror Picture Show Shadow Cast, 7pm

A Rad Cookie Bake Shop, Woodstock - A Rad Cookie August POP-UP at F&M Bank in Woodstock, 3pm

Blu Design Co., Purcellville - 08/01 Beads + Besties Half Day Camp, 10am

Barns of Rose Hill, Berryville - Good Ol' Charles Schulz Screening, 7pm

Bright Box Theater, Winchester - Lucas Jagneaux & The Roadshow w/ Justin Clyde Williams, 8pm

Winchester Brew Works, Winchester - Franklins BBQ @ WBW!!, 5:30 pm

Ohrstrom-Bryant Theatre, Winchester - Million Dollar Quartet (multiple dates and times available)

Saturday, August 2nd

317 West Main Street, Berryville - Clarke County Farmers Market 8am - noon

Ronnie Wolford & 50 West, Capon Bridge - Capon Bridge Yard Party, 7pm

James Charles Winery, Winchester - Cousins Maine Lobster At James Charles Winery, noon-7pm

Sunset Polo, The Plains - Cosmic Vibes Night, Gates open at 5:30

Fox Meadow Winery, Linden - Culinary and Wine Education Experience (Aug 3rd, too)

Chilly Hollow Brewing Co., Berryville - Franklin’s Smokin Barnyard, 1-6pm

The Amp at Sam Michaels Park, Harpers-ferry - Laurie Berkner at The Amp at Sam Michaels Park, 11am

Wolf Gap Vineyard, Edinburg - Live Music with Ryan Jewel, 2-5pm

Dirt Farm Brewing, Bluemont - Nomini Bay Oyster Festival at Dirt Farm (Aug 3rd, too)

Barn of Harpers Ferry, Harpers Ferry - Mike Kuster and the Catoctin Cowboys, 8pm

DM Shift, Bluemont - DMShift Playing Live @ Bluemont Station, 5pm

Ghost Tours of Harpers Ferry, Harpers Ferry - Ghost Tour, 8pm

Middleburg Nomad, Middleburg - ✨🎤Karaoke @ Middleburg Nomad🎤✨, 7:30 pm

Andy's, Lovettsville - Gary Smallwood on the Patio!, 6pm

Wolf Gap Vineyard, Edinburg - Live Music with Jerry Wimmer & JJ 6-9pm

Tarara Summer Concert Series, Tuscarora - Last Child with Elizabeth’s Furnace - All Aerosmith and Big Hair Band Hits, 6pm

Loudoun Wildlife Conservancy, Purcellville - Annual Butterfly Count: Let’s Count Butterflies!, 9am

Green Frog - Altos, Shepherdstown - Green frog Saturday 8 Ball Tournament, 6pm

Shark Pit Jiu Jitsu, Winchester - Guard Passing Seminar with Brad Souders, 12pm

Shenandoah Drive, Wardensville - Bluegrass in the Barn with The Fly Birds & Hammaville, 7:30 pm

Weber's Nursery & Garden Center, Stephenson - Succulent Bowl Workshop, 11am

The Studio, Front Royal - Pet Portrait Applique Quilt Workshop, 1pm

Star Tannery Volunteer Fire & Rescue, Star Tannery - Annual Carnival, 12pm

CrossFit Durable, Haymarket - Mission 22 Community WOD/Fundraiser, 9am

Bear Chase Brewing Company, Bluemont - Pickle Party at Bear Chase!, 11am

Handley Regional Library System, Stephens City - Color Our World Summer Reading Finale, 10am

Samuels Public Library, Front Royal - Studio 330: String Theory- A Fiber Arts Club, 2pm

Middleburg Humane Foundation, Marshall - Free & Low-cost Vaccine Clinic, 9am

South Mountain Spirits, Funkstown - Rosie & Cheeks Moonshine Tasting Event, 3pm

Berkeley County Youth Fair, Martinsburg - 4-State Garden Tractor Pull, 6pm

Bluemont Vineyard, Bluemont - Sunflower Brunch, 11am

Sunday, August 3rd

Main Street, Front Royal - Farm to Market on Main farmers market, 9am-2pm

Reitano Vineyards, Front Royal - National Watermelon Day, noon-4pm

West Oaks Farm Market, Winchester - Peaches and Beaches Festival, 11 am-5pm

The Studio, Front Royal - Paint Your Pet's Portrait Paint Party, 1pm

The Catamount Lounge, Front Royal - Grown Up Show And Tell (THEME: CHILDHOOD), 7pm

Drift Nirvana, Summit Point - Two Track Challenge: Washington and Jefferson, 7am

Box Office Brewery, Strasburg - Open Mic!, 6pm

Archwood Green Barns Farmer's Market, The Plains - Archwood Green Barns Farmers' Market 2025, 10am

Lost Barrel Brewing, Middleburg - Sunday FUNDay: Junior Woman's Club of Loudoun, 2pm

Chrysalis Vineyards, Middleburg - White Wine Weekend, 12pm

Erika Marie Ceramics, Berryville - Funky Clay Chicken Workshop, 12pm

The Vintage Barrel at Faithbrooke, Luray - Michel Fonne Comes to The Barrel!, 2pm

Wolf Gap Vineyard & Winery, Edinburg - Matt Palmieri Live at Wolf Gap Vineyard, 2pm

Berkeley County Youth Fair, Martinsburg - BCYF TRUCK & TRACTOR PULL, 5pm

Western Maryland Catfish Tournament Trail, Williamsport - WILLIAMSPORT - STOP #5, 7pm

Lost Barrel Brewing, Middleburg - DOG DAYS OF SUMMER at Lost Barrel Brewing, 11am

Fit4Mom Winchester VA, Winchester - Sip and Stroll, 10am

Great Country Farms, Bluemont - Family B-I-N-G-O at the Cider Barn, 2pm

Reitano Vineyards, Front Royal - CBD Music @ Reitano Vineyards, 1pm

Barrel Oak Winery and Brewery, Delaplane - Sunday Country Social: Line Dancing, Laid-Back Vibes & Vineyard Views, 11am

Monday, August 4th

Atlantic Pro Pulling, LLC., Martinsburg - Berkeley County Youth Fair - Martinsburg, WV, 6pm

Lark Brewing Co., Aldie - Bingo Night, 6:30 pm

Berkeley County Youth Fair, Martinsburg - Atlantic Pro Pulling Truck & Tractor Pul, 6pm

Let There Be Rock Schools - Leesburg, VA, Leesburg - Let there be Rock Summer Camp, 10am

Tail Race Farm, Aldie - August 4th-8th Tail Race Farm Horseback Riding Camp, 9am

Comic Kung Fu, Winchester - Board Game Mondays, 5-10pm

Tuesday, August 5th

Vibrissa Brewing, Winchester - Trivia Night, 6:30pm

Winchester Police Department, Winchester - National Night Out 2025, 5pm

Woodstock Enhancement, Woodstock - National Night Out, 6pm

Berkeley County Youth Fair, Martinsburg - BullRide Manio Rodeo, 7:30 pm

Front Royal Police Department, Front Royal - National Night Out 2025, 5pm

Berryville Main Street, Berryville - Clarke County National Night Out 2025, 6pm

Honey & Hops Brew Works, Front Royal - 🎶✨Music Bingo✨🎶, 7pm

Lovettsville's Summer on the Green, Lovettsville - Lovettsville's Summer on the Green Special Event - National Night Out & The Wild Robot, 6pm

Town of Stephens City Police Department, Stephens City - National Night Out 2025, 6pm

Purcellville Police Department, Purcellville - Purcellville PD- National Night Out, 5:30 pm

HEAT Program, Middleburg - National Night Out in Middleburg, 6pm

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