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  • Applefest

    Historic Downtown Bowmanville Bowmanville, Ontario, Canada

    Apple-themed street festival and artisan market.

  • Doors Open Whitby

    Multiple heritage and cultural sites across Whitby Whitby, ON

    One-day heritage event, 2026 theme “every door tells a story.” Participating sites: Burr Lodge; Camp X Memorial, Intrepid Park (presentations 11 a.m. and 2 p.m.); Fieldgate Sports Complex; Lynde House

  • Fall Fling (October 17)

    Millennium Square Pickering, ON

    City-run fall festival with artisan vendor market, pumpkin painting, crafts, face painting, live music, and free giveaways. October 17 activities include a scavenger hunt and line dancing. Drop-in.Municipality: PickeringOfficial event

  • Oshawa Halloween Boo Bash

    Downtown Oshawa King Street East between Simcoe Street and Mary Street, Oshawa, ON

    Free 2nd-annual outdoor Halloween street festival (“King Street Kreepshow”) presented by Oshawa Tourism: live punk/rock music, theatrical scare performances, roaming costumed characters, vendors, downtown trick-or-treating, and a Krampus street party.

  • Prologue Cross

    Elgin Park 55 Elgin Park Dr, Uxbridge, ON

    Ontario Cycling-sanctioned Ontario Cup cyclocross round with full category racing plus beginner extras — free kids’ course and race with prizes, women-only guided ride, open Try-a-Ride. Spectators get free coffee,

  • Box Office Books and Brews: The Housemaid

    Ajax Centre for the Arts 78 Church St. S., Ajax, Ontario, Canada

    Film screening and facilitated book discussion, presented with Ajax Public Library.

  • Rooted In Art: 60 Years Together

    Ajax Creative Arts 22 Sherwood Rd. West, Ajax, ON

    Fine art show and sale celebrating 60 years of Ajax Creative Arts, featuring 20+ local artists with artist demonstrations, a kids’ art table, a tea room, and free draws. Drop-in.Municipality: