The holidays are officially taking over WindsorEats Food Hall! From November 14 to December 31, Tinseltown Windsor is popping off with cocktails, cookies, cocoa, and more holiday fun than you can shake a candy cane at. Here’s the complete schedule to all the festive goodness coming your way.
🎉 Opening Night – Friday, November 14
Kick things off in style with our Opening Night featuring live tunes from the Myskow Brothers from 7–10pm. Expect holiday cheer, cocktails, and all the insta-worthy vibes.
🎲 Board Game Night – Saturday, November 15
Channel your inner strategist with Living Room Board Game Night while enjoying the sounds of New Standard from 7–10pm. Fun, games, and music? Yes, please.
🎅 Santa’s Sipping Scavenger Hunt – Friday, November 21
Put your holiday sleuthing skills to the test with Santa’s Sipping Scavenger Hunt inside the bar from 7–10pm. Clues, cocktails, and festive fun await.
🏅 Elf Olympics – Saturday, November 22
Team up and compete in the Elf Olympics while Avonlea sets the soundtrack from 7–10pm. Let the games—and holiday chaos—begin!
🎨 Ornament Decorating & Paint Night – November 28–29
Get crafty with Ornament Decorating on Friday, and channel your inner artist during Paint Night on Saturday with Fontaines (duo) performing live from 7–10pm on the Saturday. Perfect for a holiday date night or friend outing.
🍪 Cookie Classes & Santa Socials – November 30
- Be A Cookie Artist Cookie Decorating Class with Cheslea: 12–1:30pm
- Santa’s Cocoa and Candy Cane Social: 2–5pm
Bake, sip, and socialize—you know, the true holiday trifecta.
🎅 Santa Pub Crawl & Gingerbread Fun – December 5–6
- Santa Pub Crawl: Friday, December 5 (6–11pm) with Avonlea playing 7–10pm
- Christmas Cocktail Class with Adriano Ciotoli: Saturday, December 6, 3–5pm
- Gingerbread House Making with The Raisbecks providing the soundtrack: Saturday, December 6 from 7-10pm
Cocktails, gingerbread, and some good ol’ pub crawl chaos—what more could you want?
📚 Book Fair for Grown Ups – Sunday, December 7
Calling all book lovers! Browse, sip, and shop at our Book Fair for Grown Ups from 2–8pm.
🔮 Spirits of Christmas Tarot Reading – Thursday, December 11
Get a peek into your festive future from 5–9pm with Sarah’s Oracle. Holiday spirits, tarot-style.
🎶 Live Music Highlights
- An East Coast Christmas with Fiddle & Friends – Friday, December 12, 6–10pm
- New Standard – Saturday, December 13, 7–10pm
- Myskow Brothers – Friday, December 19, 7–10pm
- The Fontaines – Saturday, December 20, 7–10pm
- Avonlea – Saturday, December 27, 7–10pm
All the festive tunes you need to get in the holiday spirit.
☕ Cocoa, Cookie, and Baking Fun
- A Very Cocoa Christmas with New Standard – Saturday, December 13, 7–10pm
- Santa’s Cocoa and Candy Cane Social – Sunday, December 14, 2–5pm
- Baking with Cheslea – Sunday, December 14, 2–5pm
- Be A Cookie Artist Cookie Decorating Class with Cheslea – Sunday, December 21, 12–1:30pm
- Santa’s Cocoa and Candy Cane Social – Sunday, December 21, 2–5pm
Sip, bake, repeat.
🎄 Festive Competition
- Ugly Christmas Sweater Competition – Saturday, December 20, 7–10pm
Break out the tacky sweaters!
🎉 NYE Party – Wednesday, December 31
Ring in 2026 with our NYE Party from 7–close. Cocktails, music, and all the holiday hangover prevention you can muster.
Tinseltown Windsor is shaping up to be the ultimate holiday destination in the city. Whether you’re here for cocktails, cookies, or just a little chaotic Christmas fun, there’s something for everyone. Keep an eye on our socials for updates, themed nights, and surprises along the way!
