Chicago residents can enjoy a full calendar of outdoor events this October, many of which welcome participants in costume. Below is a guide to 13 activities across the city, ranging from apple‑picking festivals to Halloween parades.

Lincoln Square Apple Fest (Oct. 2‑4)

North Lincoln Avenue between Sunnyside and Lawrence Avenues will host the annual Apple Fest. The weekend features Midwestern produce, apple‑themed foods, cider, live music and kids’ activities. The Jesse White Tumblers will perform on Friday evening. Admission is free with a suggested $5 donation at the gate.

Bike Ride to Apple Fest (Noon, Oct. 3)

Meet at the Welles Park Gazebo in Lincoln Square for a leisurely eight‑mile bike loop that departs at noon and arrives at Apple Fest by 1 p.m. The Femmes and Thems Bike Chicago group welcomes all types of micromobility, including e‑bikes, cruisers, trikes and scooters. Riders should bring sunscreen, snacks, bike locks and water.

Chicago BIPOC Bird Walks (6:30‑8 a.m., Oct. 5, 12, 19, 26)

Big Marsh Park in South Deering offers free weekly bird walks for all skill levels. Ten pairs of binoculars are available for borrowing, and indoor restrooms are on site. No registration is required; participants simply show up. These walks are organized for BIPOC attendees.

West Loop Walking Tour (4‑5:30 p.m., Oct. 4)

Connie Fairbanks, author of the West Loop’s history, leads a one‑mile walking tour in partnership with the Chicago History Museum. The tour explores the neighborhood’s development from the 19th century to today. Tickets cost $25, or $22.50 for museum members.

Begyle Brewing & Dovetail Brewery Malt Row Block Party (Oct. 10‑11)

Located at 1800 W. Cuyler Ave. in North Center, the breweries will host a block party with special beers, food trucks, live music and family‑friendly activities. A $5 suggested donation supports The Friendship Center food pantry. The event is dog‑friendly and includes an “Oktoberfestiversary” celebration.

Jefferson Memorial Park Fall Festival (11 a.m.–2 p.m., Oct. 11)

This free festival in Jefferson Park offers pumpkins, arts‑and‑crafts stations and a costume swap where participants can donate or trade Halloween outfits.

Grand Crossing Movies in the Parks (7‑8:30 p.m., Oct. 17)

Grand Crossing Park will screen the classic horror film “A Nightmare on Elm Street” for all ages. Admission is free.

Lincoln Park Zoo Adults‑Only Halloween Festival (6:30‑10 p.m., Oct. 23‑24)

The zoo opens after hours for a 21+ Halloween celebration featuring beer and cider tastings, pumpkin‑carving demos, a costume contest, live DJ sets and unlimited rides on the carousel, giant slide and Ferris wheel. Tickets are $65 in advance or $70 on the day of the event.

Northalsted Dog Costume Parade (10 a.m.–2 p.m., Oct. 24)

Dog owners can register for a $5 fee to join a Halloween pet parade along Halsted Street from Aldine to Cornelia Avenue. Participants receive a tote bag for giveaways and can have their pets photographed with Miss Foozie on the Lark patio, followed by an after‑party brunch.

Arts in the Dark Parade (6‑8 p.m., Oct. 24)

The parade returns to Columbus Drive, moving from Balbo Drive to Monroe Street. Organizers expect about 100,000 visitors. The free, family‑friendly event features costumes and artistic floats celebrating Halloween.

Women’s Weekend at Big Marsh Park (Oct. 24‑25)

Mountain bike and BMX riders who identify as female, trans or non‑binary are invited to a two‑day weekend of instruction, clinics, group rides and optional overnight camping.

Garfield Park Conservatory Nature Day (4‑7 p.m., Oct. 28)

This indoor/outdoor event offers free admission to the Conservatory and includes animal experts introducing kids to insects and bats, craft stations, candy and prizes.

Mack’s Bike & Goods Halloween Ride (5‑10 p.m., Oct. 29)

Cyclists in Evanston are encouraged to wear costumes for a group ride that loops around North Evanston, followed by a candy toss on Lincoln and Harrison Streets. Participation is free, though donations are collected for Sanctuary Evanston.

Chicago’s October calendar provides ample opportunities for families, cyclists, pet lovers and history enthusiasts to enjoy the city’s parks, neighborhoods and cultural venues while celebrating the season.

Original reporting: Block Club Chicago — read the source article.