City Island Avenue is about to change color. On Saturday, October 24, residents will paint Halloween scenes onto shop windows along the avenue, kicking off a two-week run of island events that ends with the City Island Chamber of Commerce Halloween Parade on Saturday, October 31. Here is what is on the calendar, all of it on the island's one main street in the Bronx.

Witch Con at the American Legion, Friday, October 23

The first Halloween event on the Chamber's community calendar is Witch Con, set for Friday, October 23, at 7 p.m. at American Legion Post 156, 550 City Island Avenue. The post, named for Leonard H. Hawkins, hosts the evening, and the Chamber lists it among the island's Halloween events. The post's own website has details on the night.

Halloween window painting, Saturday, October 24

The morning after, the avenue becomes a canvas. Window painting starts at 9:30 a.m. on Saturday, October 24, along City Island Avenue. Supplies are free and are handed out at Hawkins Park, the small triangle park on City Island Avenue between Fordham Street and Hawkins Street. Painters take their materials to participating storefronts up and down the strip, so by afternoon a walk from the bridge end of the island to the seafood houses at the south end should show the results. Questions go to the organizers at cityislandhalloween@gmail.com, the contact listed on the Chamber's event page.

The painted windows stay up through the following weekend, which means they will be on view as the backdrop when the parade comes down the avenue on October 31.

A Halloween party at Sea Shore, Friday, October 30

Sea Shore Restaurant, at 591 City Island Avenue near the southern tip of the island, has a Halloween party on its Chamber listing for Friday, October 30, from 6 p.m. to 10 p.m. The listing gives the time and place; call the restaurant for the menu and any costume details. Man Overboard Sports Bar, at 247 City Island Avenue, also has an all day Halloween listing for Saturday, October 31.

The Halloween Parade, Saturday, October 31

The main event is the Chamber's own Halloween Parade on Saturday, October 31, with a 5:30 p.m. start at Hawkins Park. The Chamber sponsors and organizes it It falls on a Saturday this year.

Last year, according to the Chamber's look back at the 2025 parade, crowds filled City Island Avenue and costumed judges spread out through the crowd to pick winners. Categories in 2025 were Best Group, Best Female, Best Male, Best Boy, Best Girl, Best Infant, Best Pet, Scariest and Most Original, with honorable mentions on top. The 2025 winners included a family dressed as Moana and the ocean, a Sherlock Holmes, a baby dressed as a Sabrett hot dog vendor and a dog dressed as a cow. Ron Terner of Focal Point Gallery photographed the day, and the Chamber posted the album and video afterward.

Getting there and planning the day

City Island is reached by the City Island Bridge from Pelham Bay Park. Without a car, take the 6 train to Pelham Bay Park, the last stop, and transfer to the Bx29 bus, which runs over the bridge and down City Island Avenue. Hawkins Park is a short walk from the bridge end of the avenue.

Quick reference: Witch Con, Friday, October 23, 7 p.m., American Legion Post 156, 550 City Island Avenue. Window painting, Saturday, October 24, 9:30 a.m., free supplies at Hawkins Park. Sea Shore Halloween party, Friday, October 30, 6 p.m. to 10 p.m., 591 City Island Avenue. Halloween Parade, Saturday, October 31, 5:30 p.m., Hawkins Park. The Chamber posts updates on its community calendar at cityislandchamber.org.

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