The 2019 Guide to Halloween in Winchester

Excited for Halloween, but not sure what to do? Don’t freak out! Instead, let out a sigh of relief because we’ve got you covered. Here is a guide compiling some of Winchester’s Halloween happenings all throughout the month.

Blog post by Winchester-Frederick County Tourism intern, Paige Bridgeforth

Hill High Farm Presents: Haunted Nightmares and Other Events

Prepare to face your greatest fears at Hill High Farm’s Haunted Nightmares haunted house attraction. The house will be open through November 1st, 2019. For younger guests, they will be open during daylight hours on Saturdays and Sundays with a less-intense show. If you are eager for more scares, also check out The Last Ride. This is a “buried alive” simulator where you can lay in a casket to see what it’s like while still being able to get out afterwards. If spooky isn’t your cup of tea, they will also be hosting a slew of other activities such as escape rooms, a moonlit hayride, and a corn maze. For more information on these activities and their hours of operations for the haunted house, visit the Hill High Farm website. 933 Barley Lane, Winchester, VA 22602 Hill High Farm

Easely Created 

In the spirit of the season, Easely Created will be hosting a slew of Halloween-themed nights all throughout the month of October – and each night offers a different finished product. A sample of classes include: Hocus Pocus Door Hanger Paint Class, Hocus Pocus Sign DIY Workshop Class, and All Ages ‘The Great Pumpkin’ Paint Day 16×20 Canvas. New to painting? That’s okay! These classes are intended for anyone interested in painting and for all levels! For more information on specific classes and dates, check out their website. 47 W Boscawen St, Winchester, VA 22601

Courtesy of Easely Created’s Facebook Page

Worlds Away Escape: Redstar Sanatorium

Grab a few of your friends and head downtown to check out the latest escape room by Worlds Away Escape. The recommended number of players is 4-6 with 8 being max capacity. This room is horror-themed and features loud audio/music with strobe/flashing lights. Think you can solve the way out? For more information on this room, their other offered rooms, and for booking, check out their website. 9 N Loudoun Street, Suite 105, Winchester, VA 22601

Courtesy of Worlds Away Escape Website

October Happy Hour Run/Halloween Scavenger Hunt

Grab your sneakers because its time for Runner in Training‘s monthly happy hour run, but this time is different! This run will be in conjunction with their 3rd annual Halloween Scavenger Hunt. On October 18th, 2019 from 6pm-9pm, teams will have exactly one hour to race across Winchester finding the items needed and taking photos. Return back to Escutcheon Brewery to see which team ends up with the most points. Whether you win or lose, everyone can finish the evening off with a fresh pint. 141 W Commercial St, Winchester, VA 22601

Courtesy of Runner in Training’s Facebook Page

1st Annual Spooktacular Ball

Double, double toil and trouble! Come grab a Witches’ Brew or a Bloody Mary at this year’s Spooktacular Halloween Ball.  The Youth Development Center‘s first annual ball will be on October 19th, 2019 from 6pm-10pm. With your brew in hand, dance away the night to music performed by Meisha Herron Band. Take part in the costume contest by wearing your most hauntingly spooky costume. Also, expect to see a silent auction, door prizes, a dance competition, a cash bar, and more to be announced. Tickets can be purchased ahead of time on their website. The YDC said it best with, “It’s going to be a howling good time!” 3 Battaile Drive, Winchester, VA 22601

Halloween Trunk-or-Treat and Costume Contest

So great, it’s happening twice! The Family Drive-In will be hosting their annual Trunk-or-Treat and Costume Contest on Saturday, October 19th and Saturday, October 26th, 2019 from 5pm-7pm. As you go from trunk to trunk, make sure to catch the magic shows being performed by Kevin Owens, the face painting station, and an assortment of games. Don’t forget your best costume because there will be a costume contest with categories for children, teens, adults, and pets. The show is only beginning once trunk-or-treating is over! Screen 1 will show new releases Maleficent: Mistress of Evil and The Addams Family (2019) and over on screen 2 will be Zombieland: Double Tap and Joker. Keep checking their website or their Facebook page for when tickets go on sale. 5890 Valley Pike, Stephens City, VA 22655

Olde Towne Halloween Faire

Things are about to get a little bit spooky along the Loudoun Street Mall. This year, don’t just expect the usual trick-or-treating. The Olde Towne Halloween Faire will take place on Saturday, October 26th, 2019 from 4pm-7pm. Along with trick-or-treating, look for all kinds of new games and activities from kids of all ages. As you stroll along admiring the decorated storefronts, each participating business will be hosting their own game or activity. Some of these games include: Polka Dot Pot will be having a “Witches’ Hat Ring Toss” and Murphy Beverage Company will host “Mummy Bowling.” Once the sun goes down, the faire doesn’t end there. Head over to the Taylor Pavilion for a viewing of a Halloween classic, “Hocus Pocus,” or go on the family-friendly Apparition Trail tour to get a glimpse at the haunted history surrounding the Old Town Mall. 136 S Loudoun St, Winchester, VA 22601

Adults-Only Halloween Bash

Ghosts, goblins, and ghouls! Oh, my! All creatures are welcome for this creepy evening at the winery. On Saturday, October 26th, 2019, James Charles Winery & Vineyard has got you covered for an Adults-only Halloween Bash from 8pm-Midnight. As the rhythmic beats of BKDJ Paramount keep the night going, try a glass of Witch’s Brew! A glass of brew is included with the ticket purchase and additional glasses are only $5. Sexi-Mexi will be on-site serving up a wonderful selection of food for the evening. But don’t leave before 10pm or risk missing the costume contest. Prizes will go out to the best female, best male, and best couples costume. Tickets can be purchased online in advanced on their website or at the door, but beware. If the event is sold out, door tickets will not be available. 4063 Middle Rd, Winchester, VA 22602

Courtesy of James Charles Winery & Vineyard Facebook Page

Haunted History Ghost Tours

Ever wondered where the spirits of Winchester lie? These guided tours give you an in depth look at the mysteries found in Winchester’s history. As you glide along the streets and through the buildings of Old Town, the expert guide will tell historic tales and true ghost stories. There are three chances to go on this tour, Saturday, October 26th, Wednesday, October 30th, and Thursday, October 31st, 2019, all starting at 6pm. The tour lasts approximately one hour. Tickets for the tour must be bought in advance at the Winchester-Frederick County Visitors Center (1400 S. Pleasant Valley Rd, Winchester, VA 22601). Tickets are $10 and can be purchased with cash or check only. Each tour has a limit of 25 participants. For more information, call (540)-542-1326. Be prepared to have this tour leave you with goosebumps! Tour meets on the intersection of Cork St. and Loudoun St. Mall

History and Hauntings 

On Saturday, October 26th and Thursday, October 31st, 2019, the history of Valerie Hill Winery’s Manor House comes alive. Their ever-popular event known as “History & Hauntings,” allows guests the opportunity to listen to stories of first-hand accounts of experiences with the residential ghosts – such as the famous woman in the cellar that calls for help, and the spirit of a boy perpetually locked in the attic. Tickets include dinner by Village Square Restaurant, a glass of wine of your choice, and a detailed tour of the Manor House which focuses on the history and documented paranormal activity. This event is for adults 21 and over. For information on the event, check out their website. 1687 Malboro Road, Stephens City, VA 22655

Photo Courtesy of Valerie Hill Winery’s Website