As the summer season slowly yields into the fall season, we begin to compile the best that Winchester and the surrounding areas has to offer associated with the Halloween Season, oftentimes no matter how remotely connected to everyone’s favorite and frightful time of year. We’re gathered pumpkin patches, movie showings, haunted houses, ghostly pub crawls, trick or treating events and whatever else lurks at the bottom of deep, dank graves everywhere. Be sure to check back often and even review our Dream Weaver Team Winchester Events Page for all manner of things to do to celebrate what easily is our favorite holiday!
Hedgebrook Farm Market and Pumpkin Patch: Pick-your-own apples and pumpkins, see farm animals, and more! 690 Shady Elm Rd. (Route 651), Winchester, VA. Phone: 540-450-0310.
The Pumpkin Patch at High Hill Farm: Opens on September 23rd, The Pumpkin Patch can accommodate small groups (*minimum of 10 required) as well as large private tours. For additional information and to schedule your visit to our farm, please call us at 540-667-7377. We are very busy preparing for the upcoming season, so if no one is available to answer your call, please leave a message and we will contact you as quickly as possible.
Wilson’s Wild Animal Park & Pumpkin Patch: Fall is a special time at the Animal Park. The deer’s antlers have matured, the bears are ready to doze off for the winter and the parrots and monkeys are enjoying the last few weeks before moving into winter quarters. The beautiful fall colors and cool temps make this perfect time to have that last family outing before winter sets in. This year the Pumpkin Patch will be open from Mid-September though the end of October. As always, the pumpkin patch is free with admission to the Animal Park. 985 West Parkins Mill Road, Winchester, VA. (540) 662-5715
West Oaks Pumpkin Patch & Corn Maze: Our South location is now back open for the fall offering a Pick-Your-Own Pumpkin Patch and a new tricky Corn Maze! Call for additional details and opportunities for school field trips! We are located at: 4305 Middle Rd, Winchester, VA 22602. 540-662-6622
Wayside Farm Pumpkin Patch & Corn Maze: Get completely lost in our 10-acre corn maze. Use your sleuth skills to navigate your way through our football-themed maze. Pumpkins of every shape, color and size are plentiful in our 8-acre u-pick pumpkin field. Each fall we turn our 120-acre working farm into a unique Fall Festival with pig races, hayrides, pumpkin drops, corn mazes and much more! We are busy planning activities for this fall. Admission Costs: General Admission $10/person 2 and under FREE; Military with ID FREE; Group (10-20) $9/person; Group (20 or more) $8/person. 5273 Harry Byrd Highway, Berryville, VA 22611. (540) 539-3276
Festivals and Special Halloween Events
9/20 through Halloween: Every Wednesday and Saturday night comes the Haunted Pub Crawl from 8:30 p.m. until 11:00 p.m. Ghost Tours Old Town Winchester Virginia presents a Haunted Pub Crawl every Wednesday and Saturday night. Visit local haunts including 147 North, V2, The Half Note Lounge, Brewbaker’s, Cork Street Tavern, and the Bright Box Theater. The cost is 29.99 per person and does not include drinks. For more information and reservations, call 540-827-9948.
10/8: Murder Mystery Comedy Show: Halloween Whodunit From the people who brought you “A Merry Murder Mystery,” “The Newly Dead Game,” and “Back to the 80’s” comes “HALLOWEEN WHODUNIT!” Eat. Drink. Laugh. Solve a Murder! This Murder Mystery is one third scripted, one third improv, one third audience participation, and 100% funny.
10/14: Boo at the Zoo, Petting area, wagon rides, costume parade, bounce house and more!
10/19: Winchester Brew Works pumpkin carving party! Sharpen your pumpkin tools, watch a little Nightmare on Elm Street (or Hocus Pocus-you do you) and get in the Halloween spirit. For $15 we’ll provide you an average sized pumpkin, a carving kit (including saw-style tools; looks pretty safe) and a pint of your choice! Bringing your kids? No problem! They can get a pumpkin without the beer for $8. We’ll throw on some spooky tunes and you bring your carving A-game. Starts at 6pm.
10/21: At Marker-Miller Orchards come find the “great pumpkin” during their Pumpkin Festival! Choose from ones already picked or pick your own. Enjoy pumpkin pie, pumpkin rolls, pumpkin bars and pumpkin donuts from our bakery. A variety of food will be available at the food building. Come and enjoy this free event!
10/27: Halloween Salsa Party, Wear your best Costume👻🎃, Beginners Salsa Lessons: 9:30pm – 10pm, Party til 1:30am
10/28: Halloween Bash at the James Charles Winery! All ghosts, ghouls, goblins and zombies are invited for an evening of spooky fun at the winery, featuring party beats and lots of fun! It’s time to get creative! Whatever you wear, make it funky and fabulous and boogie through the night as your alter ego – there will even be prizes for the best costumes! Hors d’oeuvres and a glass of Witch’s Brew are included with your ticket. 8:00 p.m. until midnight; $15 in advance, $20 at the door.
10/28: Terror in the Tasting Room, Nearly 100 years ago, 320 N. Cameron St was the site of a deadly speakeasy massacre when they were discovered by local murderous teetotalers. Now, those partygoers have returned from the grave to exact their revenge upon the drinkers of today! Come in costume for an adults-only Halloween party at the Winchester Brew Works tasting room. All ghouls in costume are eligible for our costume contest! Buy a ticket in advance for heavy snacks, music from DJ Sellout and dancing, and a commemorative glass! Beer and wine will be available for purchase. $20 per person, limited tickets available. $25 at the door until sold out.
Trick or Treating
10/21 & 10/28: Family Drive In Halloween Halloween Trunk or Treat, Costume Contest & Haunted Trail – 2 BIG WEEKENDS THIS YEAR
10/28: Another option for Halloween is Old Town Winchester’s Spooktacular Celebration at 11 a.m. Saturday on the Loudoun Street Mall. The fun will kick-off with a pet parade by Posh Pets. Children can enjoy trick-or-treating at participating businesses from 2 to 4 p.m.
10/29: Sherando Safe Halloween, games, food, haunted house, cake walk and more from 1-5pm
10/29: 0 to 60 Energy Cafe is holding a Trunk or Treat in the parking lot starting at 1pm
10/29: What’s New Worship church trunk or treat from 2pm – 5pm
10/31: Winchester Announces Trick or Treating Times: Winchester Police recommend children begin trick-or-treating in the city at dusk and conclude by 8 p.m., according to a Monday news release. Residents are reminded to drive slowly all evening and look for children crossing the road. If you see any suspicious activity, report it immediately to the police department.
10/31: Stephens Landing in Stephens City will be having Trick or Treating taking place from 5:30 pm – 8:30 pm
Haunted Houses and Tours
10/20, 10/21, 10/27, 10/28: Haunted Trail at the Family Drive In, starting at 6pm each day, perfect for the whole family!
10/27, 10/28, 10/31: Haunted History Ghost Tour – Prepare yourself for a spine-tingling tour that delves into the mysterious history of Winchester! Learn of the restless spirits from the Colonial and Civil War eras often seen and heard in the streets and historic buildings of Old Town. Your expert guide weaves a tale of carefully researched history and true ghost stories that will leave you intrigued and hopefully convinced that they are here! Tour lasts approximately one hour. Tickets must be purchased in advance at the Winchester-Frederick County Visitors Center, 1400 S. Pleasant Valley Road, Winchester. Cost: $10, cash or check only. Limit of 25 participants per tour. Meet at the intersection of Cork Street and the Loudoun Street Mall. For more information, call (540) 542-1326.
All weekends, select Thursdays, and Halloween Night in October: Haunted Nightmares is an intense, high energy haunted attraction that uses the latest technology available to the haunt industry. With over 4600 square feet, trained actors, professional makeup and highly detailed sets, our haunt is not one you will soon forget. (They even have daytime events.) 933 Barley Lane, Winchester, VA. 540-667-7377.
Looking for more haunted houses in the area? Try Dark Wood Manor in Luray, The Death Trail in Dumfries, Fear Forest in Harrisonburg, The Fright Night in Ashburn, Gravensteen in DC, Haunted Hollow or Haunted Farm in Warrenton, Haunted Laurianne Woods in Gainesville, or Shocktober in Leesburg.