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🕯️ The Haunted Edition: 👻 Ghosts, 😈 Ghouls & 🎉 Good Times 🎃

Winchester Wire #029: Haunted spots in Winchester, events and happenings this weekend and more.

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Winchester Wire
October 29, 2025

Hey Winstigators!

Halloween is on Friday and I’ve been doing some digging (with help from loyal readers!) into Winchester’s most haunted spots. Here’s are the top 5 places to hear strange knocks in the night and spot a ghost:

  1.  Abram’s Delight: This is the oldest house in Winchester and it dates back to 1754. Legend has it that Mary Hollingsworth (a key figure in the history of Winchester who may have disguised herself as a man to spy for the Confederacy) used her family home as a gathering place for Quaker meetings. She lived most of her life at Abram’s Delight, only leaving the property in her final years. Now, many people believe she never really left as visitors have reported objects moving on their own, vases being knocked over and strange noises. Some even claim to have seen a figure in old Quaker clothing; possibly Mary herself, forever watching over her family home.

  2. Cork Street Tavern: A lot of you might know it as a great bar in downtown Winchester located in an early 19th century building but it’s also allegedly haunted by two ghosts: Emily and John Mann, names given by the restaurant staff. John has been reported as being seen in a long black coat and Emily has been heard calling out for him. People at the restaurant have reported being tripped by unseen forces and one paranormal investigator in 2009 said, “Nothing holds a candle to Cork Street.”

  3. 135 North Braddock Street (Lloyd Logan House/Kimberly’s): Lloyd Logan was a local tobacco merchant and around 1850 he built the house that is now Kimberly’s. When the Civil War started, the house was taken over by Union generals and under their orders, Logan was jailed and the house was confiscated for the army. Logan’s wife and daughters were also forced to leave the property and it’s believed that this moment might be a part of the reason for the paranormal things seen in the home.

    Walking along Braddock Street, pedestrians have looked up at windows on the second floor and seen the ghost of a man pacing and waving his arms in frustration. Employees of Kimberly’s have also seen the same man in that room and have said they’ve also seen a woman crying in the corner.

  4. 103 North Loudoun Street (Village Square Restaurant and V2 Bar): This building used to be Miller’s Apothecary which was opened in the middle of the 18th century and run by the same family all the way up through 1992. People that have owned and operated the building since then have seen various spirits, most notably one named Jeannette, a woman who lived with the family in the 18th century.

    During the Civil War, Union soldiers were held in the upstairs rooms of this building and people have also reported hearing voices of arguing soldiers and their footsteps.

  5. 33 North Loudoun Street: On July 20th, 1864, during the Battle of Rutherford’s Farm, Confederate Captain Randolph Ridgeley was severely wounded. A young woman in her mid-20s named Matilda “Tillie” Russell found him and nursed him throughout the night. Ridgeley survived his wounds and Russell earned the nickname “The Angel of The Battlefield.”

    For many years, locals have seen Tillie’s ghost leaving building at 33 North Loudoun street as she pulls her shawl over her shoulders and walks towards Rutherford’s Farm.

Did I miss anything? Hit reply and let me know!

Homes of the Week!

Pet Adoption!

Check out pretty-girl Ginger, ready-to-go Wooly, sweet Wynonna-Rae, shy Penny, and tiny tyrant Harley.

Events and happenings in Winchester and the surrounding territories this weekend:

Friday, October 31st:

Shenandoah River State Park, Bentonville - Fall Foliage Wagon Rides, 2 PM

On Cue Sports Bar & Grill, East Main Street, Front Royal, VA, USA, Front Royal - Its a M**der..a party..and a Dinner!, 6:30 PM

Skyline Sports Bar, Front Royal - ZomBAES & Chardonnay: Halloween Bash, 7 PM

Charles Town, WV, Charles Town - PotterWeen in Downtown Charles Town, 6 PM

Backseat Events, Winchester - Backseat's Haunted Metal Bash, 8 PM

Bakerton Market, Harpers Ferry - Bakerton Fall Fest, 6 PM

Bear Chase Brewing Company, Bluemont - Adult Halloween Party at Bear Chase!, 6 PM

Big Timber Hatchet House & Sports Bar, Martinsburg - Halloween Party - NO COVER CHARGE, 9 PM

Touch of Texas, Bunker Hill - Halloween Costume Party 21+, 8 PM

Chester Street Tavern, Front Royal - Halloween Party at Chester Street Tavern, 7 PM

King's Tavern & Wine Bar, Leesburg - NoVA Singles Halloween Party, 8 PM

Saturday, November 1st:

Warren County Fairgrounds, Front Royal - CAR SHOW: Benefiting Cars Changing Lives, 10 AM

Museum of Shenandoah Valley, Winchester - Holiday Wreath Sale, 10 AM

Hollywood Casino, Charles Town - Voyage: Celebration of the Music of Journey, 8 PM

Downtown Charles Town Historic District, Charles Town - Sunset Market…Under the Lights on Charles St., 4 PM

Big Timber Hatchet House & Sports Bar, Martinsburg - Halloween Party - NO COVER CHARGE, 9 PM

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

The Book Shelf, Winchester - Guest Reading: Half Tail Tarot, 11 AM

Sky Meadows State Park, Delaplane - A Fall Tree-mendous Hike, 10 AM

Bonfire Bookstore & Yarnery, Woodstock - Adult Scary Story Night, 7 PM

The Radical, Brunswick - Day of the Dead Party, 12 PM

Blue Fox Billiards Bar and Grill, Winchester - Cedar Creek Grade Halloween Party, 9 PM

Winchester Moose Lodge, Winchester - The SideMen, 7 PM

Hollywood Casino at Charles Town Races, Charles Town - Voyage - Celebrating The Music of Journey, 8 PM

Bluemont Station Brewery & Winery, Bluemont - Dia de los Muertos!, 2 PM

Warren County Fairgrounds, Front Royal - Charity Car Show, 11 AM

Orlean Market & Pub, Orlean - ADWELA- For the love of Reggae, 7 PM

Sunday, November 2nd:

Frederick County Public Libraries, Brunswick - Dress and Dance in Jane Austen’s World, 2 PM

Kimberly’s, Winchester - Holiday Open House Nov 2-6

National Humane Education Society, Charles Town - Cattery Yoga at Briggs Animal Adoption Center, 2 PM

Drum Orpheum Rehearsal Hall, Winchester - Drum Fever Workshop, 5 PM

Barns of Rose Hill, Berryville - Bubbles & Brunch Benefit, 1 PM

Gray Ghost Vineyards, Amissville - Wine Library Tasting at Gray Ghost Vineyards, 1 PM

Blue Valley Vineyard and Winery, Delaplane - Sammie&Shree@Blue Valley Vineyard, 1 PM

Hanging Rocks Ice Cream, Romney - Santa & Mrs. Claus at Hanging Rocks Ice Cream, 4 PM

Dirt Farm Brewing, Bluemont - Paint and Sip with Brushstroke Art, 1 PM

Beverly Equestrian, The Plains - Wk 2: Fall USEF Jumper Classic, 9 AM

Wolf Gap Vineyard & Winery, Edinburg - The Fever Project at Wolf Gap Vineyard, 2 PM

Chilly Hollow Brewing Company, Berryville - Chilly Hollow Brewing Company - Mack Berry, 2 PM

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Have fun out there!