HalloWinchester is a celebration of all the incredible autumn and Halloween events happening throughout October in Old Town Winchester! Whether you’re into harvest festivals, horror movie trivia, costume parties—or all of the above—our Old Town businesses have you covered with a full calendar of events for lovers of all things harvesty, autumnal, and spooky.
October 12th
Pumpkin Carving at Winchester Brew Works 4 PM
October 13th
Friday the 13th Open House at Passe 10 AM–7 PM
October 14th
Author Event & Craft Project – Who Will Trick or Treat With Me? at Winchester Book Gallery 11 AM–1 PM
October 18th
Psycho Cinema Horror Film Trivia at Broken Window Brewing Company 7:30 PM
October 19th
Ace of Cups at Hopscotch Coffee and Records 7 PM
October 21st
Royal Icing Cookie Class and DIY Sign Workshop at Easely Created (Halloween-themed) 2–4 PM
October 22nd
Create Your Own Pumpkin Charcuterie Board at Polka Dot Pot 4 PM
October 24th
Thrifty Tuesday $25 Paint Night at Easely Created (Hocus Pocus theme) 6:30 PM
October 26th
Runners’ Retreat Halloween Scavenger Hunt Fun Run 6–7 PM
Halloween Trivia at 50/50 Taphouse 8:30 PM
October 27th
Hideaway’s Mad Masquerade & Costume Contest 7–10 PM
Monster Bash at Piccadilly’s Public House 8 PM
October 28th
- Halloween Open House at The Quirky Closet 10 AM–5 PM
- Fairy Hair with The Tinsel Divas at The Quirky Closet 11 AM–5 PM
- Posh Pets’ Spooktacular Pet Parade and Costume Contest 1–2 PM
- Old Town Trick-Or-Treat 2–4 PM
- 2nd Annual Boos and Brews Brewery Crawl 4–10 PM
- Willie’s Halloween Party 6 PM–12 AM
- Halloween Party at Winchester Brew Works 7–10 PM
- Costume Contest at Cork Street Tavern 7–10:30 PM
- Bright Box Halloween Costume Party 8:00 PM–1 AM
- Night of the Grateful Dead Halloween Bash at Vibrissa Beer 8–11 PM …Plus a Halloween extravaganza at the Taylor Pavilion in the evening featuring a spooky slideshow, creepy tunes, and a ghoulishly fun light show!
October 29th
- Halloween Trivia at Winchester Brew Works 2 PM
- Free Community Meal and Trunk-or-Treat at T-Bone’s Bar & Grill 1 PM
October 30th
Free Trunk-or-Treat at the George Washington Hotel 5:30–6:30 PM
