Windsor Arms Hotel

What is Windsor Arms Hotel? Tucked along St. Thomas Street just south of Bloor, this historic neo-Gothic boutique address operates as an enclave of quiet old-world luxury with three distinct culinary programs under one roof. Guests move between the Roaring Twenties-inspired Gatsby dining room with seating for up to a hundred, a collection of plush, Victorian-styled parlors dedicated to afternoon tea, and Chagall, an intimate 32-seat kosher dining room trimmed in natural stone, dark wood, and custom Italian furniture.

Windsor Arms Hotel Menu & What to Order The multi-tiered Afternoon Tea remains a perennial draw, layering classic cucumber and smoked salmon finger sandwiches with warm English scones, clotted cream, and an exhaustive cellar of loose-leaf brews. Over in Chagall, the kitchen executes a disciplined, dairy-free kosher steakhouse menu headlined by high-grade USDA cuts, crisp short rib mini tacos, and a formidable Classic Beef Wellington alongside a thoughtful vegan equivalent. At The Gatsby, anchor dinner with the seared tuna tataki or the lamb duo, supported by a deep 700-label wine list and finished with a rich Basque cheesecake.

Know Before You Go Afternoon tea seatings require advance reservations weeks ahead for weekends, while Chagall operates exclusively for dinner from Sunday through Thursday. Bay subway station is a brief three-minute walk away, though on-site valet handles street parking on St. Thomas. The Gatsby serves continuously from 7:00 a.m. until 1:00 a.m. daily, making it a reliable refuge for late-night cocktails and live music.