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If you’re looking for something fun to do during the spooky season, whether it's for the entire family or adults only, check out these Halloween events happening either in Winchester or in a nearby community:
Halloween Bash
The Winchester Chamber of Commerce, Family Action Network and Winchester Recreation Department will co-host the annual Halloween Bash Trunk-or-Treat and Downtown Trick-or-Treat on Saturday, Oct. 24, from 10 a.m. to 12:30 p.m.
The Downtown Trick-or-Treat is free and open to the public.
The Downtown Trick-or-Treat will be held from 10–11:30 a.m. Local businesses in Winchester Center open their doors to trick-or-treaters for a safe, family-friendly morning.
Trunk-or-Treat will be held from 10:30 a.m.–12:30 p.m. at the Jenks Center parking lot. Local residents and organizations decorate their car trunks to hand out candy. The festival includes characters, crafts, balloon twisters, and live music.
Trunk-or-Treat is free for FAN members and $10 per family for non-members.
In the event of rain, Trunk-or-Treat moves to the Winchester Town Hall.
Hosting a Trunk
On Saturday, Oct. 24, the Family Action Network and Winchester Recreation Department will hold Trunk, from 10:30 a.m.-12:30 p.m., at the Jenks Center parking lot, 109 Skillings Road.
Hosting at trunk is free to do and is open to the public. Every trunk host receives free entry and a fan bag filled with Halloween treats.
Grab your family, friends and neighbors and get into the Halloween spirit! Decorate your trunk, hand out candy or festive treats and help make Halloween unforgettable for Winchester kids.
Email childrensevents@fanwinchester.org to sign up for this event.
Halloween Window Painting
Spooky ghosts, witches and glowing jack-o-lanterns come alive as Winchester residents paint Halloween pictures in this wonderful community event. Participants decorate the outside of designated windows of local businesses using specialized window paint.
All windows must have a “Halloween Theme.”
Sponsored by the Winchester Recreation Department, this event will take place on Saturday Oct. 24, from 1-4 p.m. or Sunday, Oct. 25, from 9 a.m.-4 p.m. Window assignments/locations with instructions will be emailed one week prior to event.
Space is limited, so register early.
Fee: $35 per window
Max 150 Participants
Click here to register.
‘Dr. Feverdream’s Halloween Experiment’
Get ready for some haunted happenings on Friday, Oct. 23 and Saturday, Oct. 24 when “Dr. Feverdream’s Halloween Experiment” returns!
For the second consecutive year, “Dr. Feverdream’s Halloween Experiment” will take over Winchester Unitarian Society (WUS), where multi-sensory installations, animatronics, immersive sets, hundreds of props, and dozens of actors promise visitors a Haunted House experience like no other.
“Dr. Feverdream’s Halloween Experiment” offers spine-chilling experiences for thrill-seekers as well as a family-friendly Rainforest Adventure path.
The single ticket grants entry into the venue where you can freely choose your experience path, whether you prefer the family-friendly Rainforest Adventure or the intense, mythological Dark Path.
Concessions and interactive games will also be open in the Haunted Hall following the walkthroughs.
The event will open on Friday, Oct. 23, from 6 to 9 p.m., at the Winchester Unitarian Society, 478 Main St. Entrance begins at 6 p.m. for the two haunted paths and the Rainforest Adventure.
The fun continues on Saturday, Oct. 23, as doors once again open at 6 p.m. for the attraction.
All ages are welcome, from 3 to 93.
Cost is $15. Tickets can be purchased here.
NEARBY EVENTS
WOBURN
Woburn Student Art Contest
The Woburn Lions Club is hosting a Halloween art contest for students. Winners will have their artwork displayed on a Halloween float during the Woburn Halloween Parade.
The deadline to submit is Oct. 15.
Submit artwork at woburnhostlions.com
Woburn Halloween Parade
On Sunday, Oct. 25, the Woburn Lions Club will present the 72nd Annual Halloween Parade, beginning at 1 p.m. on Main Street.
This year’s theme is “America’s 250 Anniversary.”
The money raised through the parade allows the Lions Club to support the following: braille books for blind children, independent living for blind adults and other physical and cognitive disabilities, veteran services, service dogs, breast cancer and many other needs in the community.
Click here for more information.
STONEHAM
Jack-O’-Lantern Nights at Stone Zoo
Stone Zoo will run Jack-O’-Lantern Nights through October, Thursdays through Sundays, 5:30-9:30 p.m.
Experience the magic of autumn after dark as Stone Zoo transforms into a glowing wonderland filled with hundreds of illuminated pumpkins, larger-than-life sculptures and family-friendly Halloween fun.
As you wander Stone Zoo’s illuminated pathways, discover dazzling carved scenes featuring classic spooky creatures and towering pumpkin sculptures reaching up to 18 feet tall. You'll also find beautifully carved animal displays inspired by species from around the world, including giraffes, rhinos, bison, butterflies and more.
Be sure to capture the memories with photo ops, including a giant pumpkin chair, pumpkin wall, scarecrow display and other festive backdrops. Along the way, enjoy seasonal snacks and beverages available for purchase to sweeten your autumn evening.
Click here for ticket information.
Medford
Sixth Annual Halloween Fest & Pumpkin Float
Date & Time: Saturday, Oct. 24, 6–8:30 p.m. (Kids Costume Parade at 6:45 p.m.)
Venue: Wright’s Pond, Medford
Description: Features a lantern-lit path, carved pumpkin displays on land and floating on the water, kids' artwork, live music, seasonal treats, and food concessions.
Cost: Free
Welcome to Deadford Halloween Ball
Date & Time: Saturday, Oct. 31, 7 p.m.-midnight
Venue: Arts Collaborative Medford, 162 Mystic Ave., Medford
Description: The venue is transformed into the legendary Deadford Manor with food, drinks by Medford Brewing Company, costumes, and music by DJ Cruz.
Cost: Ticket required (21+)
Website: Eventbrite Registration
Hall O Ween at The Great American Beer Hall
Date & Time: Saturday, Oct. 31, starting at 8 p.m. (Live music from Legends of Summer) / 9 p.m.
Venue: The Great American Beer Hall, 142 Mystic Ave., Medford
Description: Costume party featuring dancing, drinks, live music, and late-night DJ sets.
Cost: $10 at the door or advance tickets (21+)
Website: The Great American Beer Hall Event Info
Oh The Horrors! A Burlesque Show
Date & Time: Saturday, Oct. 10, 7 p.m.
Venue: Deep Cuts, 21 Main St., Medford
Description: A horror-themed evening where classic movie villains are reimagined as burlesque performers in a restaurant and bar setting.
Cost: Ticket required (18+ or accompanied by a parent/guardian)
Website: Do617 Event Listing
Halloween festival and market
Date & Time: Sunday, Oct. 18, starting at 10 a.m.
Venue: Condon Shell, 2501 Mystic Valley Parkway, Medford
Description: An outdoor daytime festival and market featuring local crafters, artists, bakers, and chefs alongside interactive games and family-friendly activities.
Cost/Tickets: Free admission, all ages.
Arlington
Halloween Dance
Date & Time: Friday, Oct. 16 at 4 p.m.
Venue: Knights of Columbus #109, 15 Winslow St., Arlington
Description: A festive, kid-friendly indoor celebration featuring music, dancing, a pizza dinner, and dessert. Costumes are encouraged. The event offers budget-friendly inclusive pricing with special rates and financial assistance available.
Cost: Budget-friendly (specific reduced/inclusive rates available).
Website: Biltne Event Page
