More than a dozen Halloween and fall events fill the calendar across Winnetka, Wilmette, Glencoe, Kenilworth and Northfield in October.
The Record North Shore, in a roundup first reported by Samuel Lisec on Sept. 30, cataloged 34 seasonal events across the broader North Shore. Here are the highlights in our five communities.
Witches rides and charity fun
The Wilmette Witches Ride starts at 3 p.m. on Saturday, Oct. 10, from the corner of Harvard Street and Birchwood Avenue. Women ride through town tossing candy, with a requested $45 donation benefiting Erika's Lighthouse, a youth mental health organization.
A week later, the Winnetka Witches Ride begins at 1 p.m. on Sunday, Oct. 18, from Hubbard Woods Park, 939 Green Bay Road, ending at Fred's Garage. The three-and-a-half-mile ride costs $75 per entry, supporting Henry's Heroes, which funds epilepsy research. Each entry includes a raffle ticket.
The big one: Night of 1,000 Jack-O'-Lanterns
The Chicago Botanic Garden's signature fall event returns Wednesdays through Sundays, Oct. 7–25, at 1000 Lake Cook Road in Glencoe. According to the garden's event page, the paths are lined with artist-carved pumpkins, including at least 75 giant gourds weighing 150 pounds each. New this year: a 20-foot illuminated sculpture called the Monarch Skull, created by artist Alyse Gamson.
Timed tickets run 6:30–9:30 p.m., with last entry at 9:45 p.m. Advance nonmember tickets cost $24 for adults and $17 for children ages 3–12. Reduced pricing for those receiving food assistance is available on select dates, with parking included. Advance online parking is $15; on-site parking costs $25.
Family-friendly frights
Wicked Wilmette takes over Gillson Park on Friday, Oct. 16, from 5:30 to 7:30 p.m. at the Lakeview Center, 800 Gillson Park Drive. Families can expect inflatables, face painting, a hayride, a costume contest and a pumpkin decorating station. Registration is required for children, and an adult must accompany each child.
Pumpkins in the Woods fills Hubbard Woods Park in Winnetka on Friday, Oct. 23, from 4 to 6 p.m. A $7 registration fee covers a pumpkin and decorations. Carnival games, bounce houses and a costume parade are free.
The Pumpkin & Paws Fall Fest, hosted by the Wilmette-Kenilworth Chamber of Commerce, runs 10 a.m.–1 p.m. on Saturday, Oct. 24, at Linden Square, 400 Linden Ave. in Wilmette. The free event features a pet parade, costume contest, petting zoo and live music.
Oct. 30–31 blitz
Three events land on Friday, Oct. 30. Halloween Hello, hosted by the Winnetka-Northfield-Glencoe Chamber of Commerce, runs 10 a.m.–5 p.m. at Glencoe Village Hall, 675 Village Court, with trick-or-treating at downtown businesses and a "Ghosts in the Garden" experience from the Glencoe Historical Society. That evening, the Northfield Park District Boo Bash runs 6–7:30 p.m. at 401 Wagner Road, with games, crafts and a train ride through Willow Park. The Wilmette Children's Theater also opens "Mary Poppins Jr." at 7 p.m., with performances running through Nov. 7. Tickets are $13 and go on sale at 10 a.m. on Tuesday, Oct. 13.
On Halloween day, Spooky Skate at Centennial Ice Rink, 2300 Old Glenview Road in Wilmette, invites all ages to skate in costume from 1 to 2:30 p.m. Entry costs $8 for students, $9 for adults and $4 for ages 5 and under. The costume contest is $5, free for ages 5 and under.
Also on the calendar
The Winnetka Golf Club Fall Scramble opens the month on Saturday, Oct. 3, at 8 a.m. at 1300 Oak St. ($120 per player, $80 for passholders). That evening, Community House Winnetka presents The Witch Project, a one-night performance by Alex Benjamin at Winnetka Chapel, 630 Lincoln Ave., at 7:30 p.m. Tickets cost $26.50.
The Winnetka Park District hosts a Fall Beach Clean Up at Lloyd Beach, 799 Sheridan Road, from 8 to 10 a.m. on Saturday, Oct. 10. Registration is recommended but not required.







