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  • 🍁🏇 Racing Into Fall: 🏆 Steeplechase Thrills, 🌧️ Stormy Skies & 🗓️ Weekend Fun.

🍁🏇 Racing Into Fall: 🏆 Steeplechase Thrills, 🌧️ Stormy Skies & 🗓️ Weekend Fun.

Winchester Wire #026: Steeplechase racing, real estate listings, events and happenings and more

Author

Winchester Wire
October 08, 2025

Hey Winstigators,

There’s a lot to do in Winchester and the surrounding territories this weekend, but I wanted to take a minute to spotlight one of my favorite annual events: The Virginia Fall Races in Middleburg.

Here’s the deal: I don’t find horseracing and steeplechasing all that interesting and I still have a blast every year. For me, the Fall Races are less about the horses as it is about the social environment and experience. It’s a great way a great way to spend a day outside in nice fall weather, hang with friends and tailgate.

There’s plenty to do and things to keep everyone entertained even if you don’t know the first thing about horses. You’ll find food trucks, tent shopping and it’s more of a family-friendly (bounce houses for the kids!) social event than anything. It’s also for a good cause; proceeds from the Fall Races go to the Inova Hospital Foundation and the preservation of Glenwood Park.

Gates open at 10 AM so there’s plenty of time to get in and get set up or check out the shopping tents and the family fun-fair area. The first race starts around 12:30 and the event goes on till about 6 PM.

Unfortunately I won’t be able to attend this year, but if you’re looking for a great fall day that’s scenic and social on Saturday, check out the Fall Races at Glenwood Park in Middleburg. Bring your friends, pack a tailgate and check out one of the best traditions in the area!

Quick reminder: Monday is Columbus Day or Indigenous People’s Day!

City offices, Jim Barnett Rec Center and the Joint Judicial Center are closed on Monday, 10/13. But the bigger news is city wide trash and recycling are going to be collected one day later than usual and there’s no yard trash pickup for the week. You can see details here. And if you’re not sure what Ward you’re located in, you can figure it out here.

Homes of the Week!

Events and happenings in Winchester and the surrounding territories:

Wednesday, October 8th

The Cider House, Winchester - Karaoke with DJ Blue Nova, 7 PM

Hazel-Pruitt Armory, Winchester - Become a Habitat Hero, 5:30 PM

Stitch Needlepoint, Middleburg - Learn to Stitch! 5-7 PM

The Union Jack Pub, Winchester - UNION JACK TRIVIA, 6:30 PM

Thursday, October 9th

Backseat Events, Winchester - Let It Begin Tour, 6:30 PM

Typewriter Studio, Winchester - Kids Art Club, 4:15-5:45 PM

Shenandoah Valley Golf Club, Front Royal - Phoenix Project’s 10th Annual Wine Pull Fundraiser, 5-7:30 PM

White Properties of Winchester, Winchester - White Properties Community Shred Day, 1 PM -3 PM

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

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

Godfrey Miller Center, Winchester - Savor the World, 5:30 PM

Winchester Rescue Mission, Winchester - Conversations on a Bench, 3 PM

Taylor Pavilion Winchester, Winchester - October Bike Nights, 5:15 PM

Beer & Wine Depot, Winchester - The Prestige of J. Bookwalter Wines at The Beer & Wine Depot!, 4 PM

Museum of the Shenandoah Valley, Winchester - Teen Art Club, 4:30 PM

Wolf Gap Vineyard, Edinburg - Swatted Lanternfly: The Massacre, Noon - 6 PM

Friday, October 10th

Raven Conjure, Winchester - Build Your Own CEMETARIUM!, 6 PM

Warren County Fairgrounds, Front Royal - Homesteaders Conference (Saturday, too)

Bonfire Bookstore & Yarnery, Woodstock - Book Launch! Christmas Jars Cookbook, 6:30 PM

Front Royal Moose Lodge, Front Royal - Ryan Jewel & full band, 7 PM

Bright Box Theater, Winchester - Music Bingo, Free Event, 7 PM

Vibrissa, Winchester - First Responder Friday’s

Franklin Park Arts Center, Purcellville - The Spin Outs present Elvis: A Live Rockumentary, 7 PM

Front Royal Visitors Center, Front Royal - Dancing Downtown Front Royal • CAZHMIERE Concert, 6 PM

Sam N Jake's, Martinsburg - Bar Feud Fridays at Sam n Jakes, 8 PM

Stone Branch Center for the Arts, Front Royal - Hold My Heart Gallery, 6 PM

American Legion, Brunswick - Brunswick American Legion - Mack Berry, 7 PM

Monk's BBQ, Purcellville - Buffett and BBQ at Monk's!, 8 PM

Angels Bar & Grill, Inwood - 80s/90s honky tonk throwdown, 9 PM

Roma Old Town Wood-Fired Pizzeria, Winchester - Dylan Woelfel LIVE at Roma Old Town, 8 PM

Apollo Civic Theatre, Martinsburg - Rumors, 8 PM

Shiloh Manor Farm, Purcellville - Murder at Shiloh Manor Farm, 6:30 PM

The Beer & Wine Shop, Winchester - October Friday² FREE Tasting!!!, 5 PM

Shawnee Springs Market & Cannery (Winchester, VA), Winchester - Weekly Beer Tasting at Shawnee Springs Market, Senseny Road, 4 PM

Hollywood Casino at Charles Town Races, Charles Town - The Breeders Classic Gala Dinner Dance, 6 PM

Easely Created Winchester, Winchester - Family Funday Paint Class at Easely Created, 6:30 PM

On Cue Sports Bar & Grill, Front Royal - LouD returns to On Cue Sports Bar and Grill, 8 PM

Blandy Experimental Farm/State Arboretum of Virginia, Boyce - Spooky Arboretum Night Hike, 7 PM

Saturday, October 11th

Murphy Beverage Company, Winchester - Beer and Halloween Candy Pairing, 2 PM

Ranson Civic Center, Ranson - Spiritual Wonders Fair, 10 AM

Winchester Book Gallery, Winchester - Author Event: Kira Young - Queen of my Garden, 2 PM - 4PM

Martinsburg-Berkeley County Parks & Recreation, Martinsburg - TRUNK or TREAT🎃, 2 PM

Bright Box Theater, Winchester - Comedy Night: Brian Enk (7pm and 9:30pm shows)

Hollywood Casino at Charles Town Races, Charles Town - Blackberry Smoke, The Reverend Peyton's Big Damn Band in Charles Town, 8 PM

The Conche, Leesburg - Art Of Cocktail Making Class, 12 PM

Movementation, Winchester - Practical Tai Chi, 11 AM

Wardensville Community Library, Wardensville - Capon Valley Fire Dept Car Show, 9 AM

Spring Mills High School, Falling Waters - READY, SET, GLOW 5K FUN RUN AND TOT TROT, 5:30 PM

Handley Choral Boosters, Winchester - Bag Bingo Fundraiser, 6 PM

Sherando Park, Stephens City - Trails 4 Miles and 1 Mile Fun Run/Walk, 8:30 AM

Touch of Texas, Bunker Hill - 🚦 Stop Light Party, 8 PM

Sunday, October 12th

Stitch Needlepoint, Middleburg - Sunday Afternoon Stitch 2-4 PM

State Arboretum of Virginia, Boyce - Wild Gathering Community, 12 PM

Museum of the Shenandoah Valley, Winchester - Dino-Con, 10 AM

Henry Arena, Martinsburg - WV05 Breast Cancer Barrel Race, 12 PM

The Venue by Brix27, Martinsburg - 8th Annual Wine & Food event, 2 PM

Blandy Experimental Farm, Boyce - NSVAS 50 Year Anniversary Celebration, 2 PM

Franklin Park Arts Center 540-338-7973, Purcellville - Planetarium: Halloween Astronomy, 1 PM

Walsh Family Wine, Purcellville - Winemaker's Apprentice Tour, 12 PM

Downtown Martinsburg, Martinsburg - classic hog roast, 4 PM

The River House, Capon Bridge - Camera Club, 1 PM

West Oaks Farm Market, Winchester - 2025 Winchester Medical Center NICU Reunion, 1 PM

Erika Marie Ceramics, Berryville - Clay Jack O’Lantern Workshop, 3 PM

Chilly Hollow Brewing Company, Berryville - Chilly Hollow Brewery - Tuff Luck Band, 1 PM

Riverbend Bar & Grill, Falling Waters - Chili Cook Off with Mark Miller, 3 PM

Godfrey Miller Center, Winchester - Stitch-in at Godfrey Miller Center, 2 PM

Bluemont Station Brewery & Winery, Bluemont - 🎃🐾 2nd Annual Paws N’ Pumpkins: A Dog-Friendly Fall Celebration 🎃🐾, 11 AM


Monday, October 13th

BikeWalk Winchester, Winchester - TalkWalk Community Walks - October, 6 PM

Lark Brewing Co., Aldie - Bingo, 6:30 PM

Bonnie's at the Red Byrd, Keedysville - Dine and Donate Spirit Night Fundraiser, 3 PM

Raven Rocks Trailhead Parking Lot, Bluemont - Raven Rocks 5.8 miles - moderately strenuous, 8:30 AM

Tuesday, October 14th

Saint Andrews Mountain Community Center, Millville - Harpers Ferry Silent Book Club, 7 PM

Vibrissa, Winchester - Trivia Night, 6:30 - 8 PM

Handley Regional Library System, Berryville - Magic: The Gathering (Weekly), 5 PM

Main Street Martinsburg, Martinsburg - Paws & Pours, 6:30 PM

Leesburg Community Church, Leesburg - Free Women's Clothing Swap, 6 PM

Handley Regional Library System, Winchester - Lineage Society Workshops with Katherine Collins, MLISc, 10:30 AM

Jefferson County Emergency Services Agency 419 16th Street Ranson, WV, Ranson - CPR / Stop The Bleed Certification Class, 9 AM

Blue Mountain Art Studio-Artist Laura Corebello, Front Royal - LITTLE ARTISTS CLASSES FOR HOMESCHOOLERS - AGES 6-8 - (GRADES 1-3)- OCTOBER SESSION, 11 AM

Harpers Ferry, WV, Harpers Ferry - Beginner Fencing Class in Harpers Ferry, 6:30 PM

Salamander Middleburg, Middleburg - October Biz Buzz, 5:30 PM

Rose Hill Park 35 E Main St, Berryville, VA 22611, Berryville - Fall Homeschool Picture Day, 10 AM

Museum of the Shenandoah Valley, Winchester - Mindfulness Walk: Forest Trail, 2 PM

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