It’s that time of year again — when local halls, churches, and bakeries transform into festive marketplaces filled with holiday cheer. From handmade crafts to home baking, these annual fairs are a cherished way to connect with neighbours and support local causes.
🎄 St. Cuthbert’s Christmas Fair
Saturday, November 8th, 11 a.m. – 2 p.m.
1399 Bayview Avenue
St. Cuthbert’s Leaside is welcoming the community back for its beloved Christmas Fair, featuring all your favourite tables — from baking and preserves to books, crafts, and gift baskets. Enjoy a boxed lunch, browse “red tag” treasures, or sip a coffee while catching up with friends and neighbours. Proceeds support St. Cuthbert’s Church and its outreach programs. Learn more about St. Cuthbert’s Christmas Fair →
🕯️ Holly Berry Fair at Rosedale United Church
Saturday, November 22, 10 a.m. – 4 p.m.
Sunday, November 23, 12 p.m. – 5 p.m.
159 Roxborough Drive
Celebrating 75 years, the Holly Berry Fair at Rosedale United Church is one of Toronto’s oldest community fairs. The weekend event offers festive shopping, live entertainment, and activities for all ages. Little ones can visit Santa’s interactive workshop (and bring their letters to Santa!), while adults explore the thrift market, silent auction (Saturday only), and a range of unique local vendors. Be sure to stop by for the deli lunch (Saturday will feature home-cooked ham!) and home baking.
100% of proceeds from the fair support the Out of the Cold food security program in downtown Toronto — helping provide meals and support to those in need during the winter months. See details for the Holly Berry Fair →
🍪 Robyn’s Cookies — Outdoor Holiday Marketplaces
Saturday, November 22 & Saturday, December 6
953 Mt Pleasant Road
Robyn’s Cookies will host two outdoor Holiday Marketplaces (plus a food drive) this season — perfect for picking up locally made gifts, sweet treats, and festive goodies in time for the holidays. Visit Robyn’s Cookies online →