Pipes by Day, Ponies by Dusk 🎵🌄🐎

Winchester Wire #020: Sunset Polo, Scottish Games, Labor Day events and happenings and more.

Author

Winchester Wire
August 27, 2025

Hey Winstigators,

Last weekend, some friends invited us out to Sunset Polo at Great Meadow in The Plains—just a quick, easy drive from Winchester. It’s a relaxed, picnic-style evening where you can spread out a blanket, drink something cold, and casually watch fast-paced polo matches as the sun sets. The vibe is totally family-friendly, with food trucks and a kids’ tug-of-war between matches to keep the little ones entertained.

There are only three weekends left in the season, so if you’re looking for a fun Saturday night outdoors with cool evening weather and a bit of tailgating, this is a great pick.

Another can’t-miss for Labor Day weekend: the Virginia Scottish Games, also held in The Plains on Saturday and Sunday. I won’t make it this year, but I’ve been several times and it’s always a blast. Expect everything from bagpipe bands and Highland dancing to athletic feats like the caber toss (think of people throwing telephone poles) plus rows of tents with Scottish crafts and heritage info. Curious about your roots? Clan booths can help you trace your tartan.

Car enthusiast? There’s a British car show featuring Aston Martins, MGs, Land Rovers and Rolls Royces. Hungry? You’ll find fish & chips, Scotch eggs, shortbread, and even whisky tastings along with standard fair snacks like fried Oreos and funnel cakes. And if you’re a dog lover, the herding demonstrations with border collies, corgis and sheepdogs are great to watch, too.

Thinking about spending a day at the Scottish Games? Here’s a family-friendly itinerary:

Morning (10:00 AM – 12:00 PM)

  • Clan Village Stroll – Start with a leisurely walk through the clan tents. Kids can collect stamps or stickers, hear stories, and snap photos with tartan-clad hosts.

  • Highland Dancing & Music – Catch the morning performances of fiddlers and dancers to get into the Scottish spirit early.

Midday (12:00 PM – 2:00 PM)

  • Lunch on the Lawn – Grab Scotch eggs, meat pies, or fish & chips while enjoying the piping & drumming competitions nearby.

  • Kid Zone Fun – Let the kids tackle mini caber tossing, a Nessie moon bounce, or try archery in the family activity area.

Afternoon (2:00 PM – 4:00 PM)

  • Heavy Athletics Finals – Watch the pros toss cabers, hurl stones, and heave weights—the big crowd pleasers!

  • Sheepdog Demos & Terrier Races – A must-see for animal lovers (and great for family photos).

Late Afternoon (4:00 PM – 5:30 PM)

  • British Car & Motorcycle Showcase – Take a stroll among classic cars and vintage bikes before wrapping up your visit.

  • Shortbread & Souvenir Stop – End on a sweet note and pick up a tartan trinket for the ride home.

Make a day of it! You could combine the two events by heading to the Scottish Games in the morning and then over to Sunset Polo when the gates open at 5:30. Two events, one easy drive!

Pet Adoption!

Check out ready-to-go Bo, Max Scherzer-eyed Aiden, happy Kia, and um…the intense Nebraska.

Events and happenings in Winchester and the surrounding territories:

Wednesday, August 27th

Bear Chase Brewing Company, Bluemont - Bingo & Brews at Bear Chase!, 6:30 pm

West Trail Wellness and Massage, Purcellville - Reiki + Yoga, 6:30 pm

Urban Easel, Martinsburg - 4 Week Intro to Pottery Workshop, 6pm

Honey & Hops Brew Works, Chester Gap - Combs & Cones Club Member Event KICKBALL, 6pm (becoming a member is easy!)

Shepherd University Center for Appalachian Studies and Communities, Shepherdstown - "I've Endured": The Music & Legacy of Ola Belle Reed Documentary & Panel Discussion, 7pm

Fauquier Agriculture Coalition, Warrenton - FAC - Community Meet-Up, 4pm

Thursday, August 28th

The Cider House, Winchester - Open Mic Showcase at The Cider House, 6pm

Shenandoah County Fairgrounds, Woodstock - Tauren Wells, 7pm

Thick-n-Thin Brewing Company, Funkstown - Bar Feud Thursdays @ Thick-n-Thin Brewing Company, 7pm

Runners’ Retreat, Winchester - RRTGR (Run Club), 6pm

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

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

Magnolias at the Mill Restaurant, Purcellville - Magnolias' Italian Wine Dinner, 6:30 pm

Slater Run Vineyards, Upperville - Desperate Flight: The Wanzer-Grigsby Escape, 6:30 pm

Brickhouse Bar & Grill, Front Royal - Anthony Taylor at Brickhouse!, 7pm

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

Muse Vineyards, Woodstock - Mountain Strings and Thursday Things, 5pm

Barns of Rose Hill, Berryville - Third Thursday Open Acoustic Jams, 5pm

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

St. Isidore Market, Charles Town - St. Isidore Farmer's Market, 5pm

The Farm Brewery at Broad Run, Haymarket - Movies At The Farm (Night At The Museum), 7pm

Handley Regional Library System, Winchester - Home Food Preservation, 6pm

The Catamount Lounge, Front Royal - Rich Ridgell @ The Catamount Lounge, 8pm

Charles Town Library, Charles Town - Adult Writing Circle, 6pm

Barn of Harpers Ferry, Harpers Ferry - Andrew Copenhaver, 8pm

Warren Heritage Society, Inc., Front Royal - An Afternoon Tea with Warren Heritage Society, 2pm

Friday, August 29th

Famous Last Words @ Piccadilly’s, Winchester - FLW BACK LIVE at PICCADILLY'S!, 7:30 pm

The Venue by Brix27, Martinsburg - Murder Mystery Dinner!, 6:30 pm

Cousins Maine Lobster, Brunswick - Cousins Maine Lobster🦞 at Brunswick Crossing, 4pm

The Goldberg School of Music, Berryville - Music in the Park - GSM final Summer Showcase!, 6pm

Dirt Farm Brewing, Bluemont - Watermelon Crawl Mountain Water Release, 12pm

Bear Chase Brewing Company, Bluemont - Friday Night Live at Bear Chase Brewing Company, 6pm

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

Eleven Eleven Brewing Company, Purcellville - Jess Jams Eleven Eleven! Live Music with Jessica Paulin, 6pm

Shenandoah County Fairgrounds, Woodstock - Crowder: Grace & Glory Tour, 7:30 pm

Willowsford Conservancy & Farm, Aldie - Tree of Heaven/Spotted Lanternfly Volunteer Workshop, 1:30 pm

Stitched by G, Berryville - a girly POP🥤hat bar✨, 5pm

Royal Cinemas, Front Royal - JAWS on the BIG Screen., 7pm

Mack Berry Band, Front Royal - On Cue Sports Bar & Grill - Mack Berry Band, 8pm

Shenandoah Downs - County Fair Association, Woodstock - Tauren Wells at Shenandoah Downs - County Fair Association, 7:30 pm

Blandy Farm, Boyce - August Bird Walk, 8am

Touch of Texas, Bunker Hill - Freedom Friday, 8pm

Newtown History Center, Winchester - Hungry for History: Valerie Hill, 7pm

Tilty McFlipperz, Martinsburg - Beer, Bistro & Bands!!, 5pm

SMV Equestrian, Middleburg - Fit and Sip : saddle fitting demo, 5pm

Barn of Harpers Ferry, Harpers-ferry - Poehemia, 8pm

Saturday, August 30th

The City of Charles Town, Charles Town - Charles Town Car Show, 10am

Bear Chase Brewing Company, Bluemont - Cars & Brews at Bear Chase!, 11am

The Monument, Winchester - Bones Owen: The Best Western Tour, 7pm

The Dark Horse Irish Pub, Flint Hill - Robbie Limon FULL BAND is Back!, 7pm

Henway Hard Cider Barn, Bluemont - Doxie Derby: Dachshund Rescue Race, 9am

DV Rides, Haymarket - DV Rides Sunset Crew, 7pm

Bright Box Theater, Winchester - Comedy Night: Winston Hodges, 7pm

Skyline Ranch Resort, Front Royal - Appaloosa Roots Music Festival, 2 day event

The Young American, Martinsburg - “Sip into Fall” — END of SUMMER BASH!, 5pm

Rack ‘Em Billiards and Games, Winchester - 8ball Chip Tournament, 7pm

Honey Hops and Brew Works, Front Royal - August homesteaders meeting, 5pm

Martinsburg Farmers Market, Martinsburg - Martinsburg Farmers Market at the Roundhouse, 10am

Winchester Book Gallery, Winchester - Author Event: Erin Mackey - Hidden World, 11 am-1pm

Winchester Book Gallery, Winchester - Author Event: Randina Sheldon, 2-4pm

Stone Branch Center for the Arts, Front Royal - Labor Day Weekend Print-A-Thon! (Aug 30 - Sept 1, 2025), 10am

Handley Regional Library System, Winchester - Thunder and Song: A Collection of Civil War Poetry Author Talk, 2pm

Patsy Cline Historic House, Winchester - 15th Annual Patsy Cline Block Party, 10am

Monk’s BBQ, Purcellville - Cowpoke @ Monk’s, 8pm

Shenandoah Valley Chess Club, Stephens City - Chess at Bowman Library, 10am

Ruby Yoga, Front Royal - Meditative Goat Yoga, 11:30 am

Sunday, August 31st

Shafer Memorial Park, Boonsboro - 5th Annual Boonsboro Food Truck Festival, 12pm

The Handcrafted Board @ Chilly Hollow Brewing, Berryville - Charcuterie Workshop, 11am

Estate Vineyards, Hillsboro - LoCo Fest 2025, 12pm

Lost Barrel Brewing, Middleburg - Live Music by Scott Kurt at Lost Barrel Brewing, 1pm

Winchester Book Gallery, Winchester - Author Event: Elaine Honeycutt - Chop It Chip, noon-2pm

Shenandoah River State Park, Bentonville - Gundalow Racing, 3pm

Wolf Gap Vineyards, Edinburg - Yoga With Aimee, noon - 1pm

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

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

Robey Meeting Room at Purcellville Library, Purcellville - Yoga for Beginners, 1pm

Barrel Oak Winery and Brewery, Delaplane - Western Sundays at Barrel Oak, 11am

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

Wolf Gap Vineyard & Winery, Edinburg - Family Movie Night at Wolf Gap Vineyard & Winery, 8:30 pm

Alamo Drafthouse, Stephens City - Invasion '53 at GenreBlast, 11am

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

4Js Farm and Brewery, Warrenton - 4Js Farm Days, 2pm

Josephine School Community Museum, Berryville - Book Club Discussion, 3pm

Lost Barrel Brewing, Middleburg - Sunset Sessions at Lost Barrel Brewing, 6pm

Monday, Sept 1st

Wolf Gap Vineyard & Winery, Edinburg - Adeline Csontos at Wolf Gap Vineyard, 2pm

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

Chilly Hollow Brewing Co., Berryville - Pop Up Soda Bar: Overflow Soda Co, noon-6pm

Bear Chase Brewing Company, Bluemont - Labor Day at Bear Chase!, 11am

Lost Barrel Brewing, Middleburg - Labor Day Margaritaville Bash, 11am

The Farm Brewery at Broad Run, Haymarket - Labor Day Luau, 11am

Lost Barrel Brewing, Middleburg - Beer Release: Blueberry Lemon Gose, 12pm

Shepherdstown Community Club, Shepherdstown - Annual Labor Day Picnic & Boot Sale, 10am

Brunswick HS Running, Knoxville - Othello Park Labor Day 1k & 5k, 7am

River and Trail Outfitters, Knoxville - White Water Rafting on Labor Day, 10am

Olde Mother Brewing Co., Frederick - Pages & Pints: An Olde Mother Brewing Book Club, 6:30 pm

Tuesday, Sept 2nd

BikeWalk Winchester, Winchester - BikeWalk Open Meeting, 6:30 pm

Vibrissa, Winchester - Trivia Tuesday, 6:30pm

Honey & Hops Brew Works, Front Royal - Music Bingo- Decades 🎸, 7pm

Barns of Rose Hill, Berryville - Trivia Night!, 7pm

Shenandoah County Library, Edinburg - Preschool Story Time, 10:30 am

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!