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Concert

Symphony in the Gardens: Sinatra & Friends PT. 2

Monday, August 31, 2026 · 7:30 p.m. – 7:30 p.m.·Casa Loma·$63
Symphony in the Gardens: Sinatra & Friends PT. 2 event
Event Websitevia ticketweb.ca
Date

Monday, August 31, 2026

Time

7:30 p.m.7:30 p.m.

Venue

Casa Loma

Address

1 Austin Terrace

There is something undeniably magical about spending a summer evening at Casa Loma, and the Symphony in the Gardens series captures that feeling perfectly. Perched atop the escarpment in the prestigious Casa Loma neighbourhood, the castle serves as a dramatic, gothic backdrop to the Glass Pavilion, where Maestro Paolo Busato and the Casa Loma Symphony Orchestra curate an experience that feels worlds away from the frantic pace of downtown Toronto.

A Night of Ol' Blue Eyes

This particular instalment of the series is a love letter to the Chairman of the Board himself. Frank Sinatra’s music has a unique ability to bridge generations, and hearing these arrangements performed by a full symphony orchestra—rather than a standard big band—adds a lush, cinematic texture to classics like "Fly Me to The Moon," "My Way," and "Cry Me a River." Under the artistic direction of Maestro Busato, the orchestra leans into the sophistication of the Great American Songbook. Expect a performance that balances the technical precision of a symphony with the loose, improvisational spirit of a Vegas showroom. It is the kind of show that demands a glass of scotch in hand and a bit of finger-snapping as the sun dips below the Toronto skyline.

The Venue: A Midtown Jewel

Casa Loma is more than just a tourist attraction; it is a piece of Toronto history. Built by Sir Henry Pellatt in the early 20th century, the castle’s sprawling estate gardens offer one of the most unique vantage points in the city. While the interior of the castle is a marvel of Edwardian architecture, the outdoor Glass Pavilion allows you to soak in the humidity of a Toronto August evening while remaining sheltered from the elements. The juxtaposition of the rugged, historic stone of the castle against the modern, airy pavilion creates an atmosphere of refined elegance that you simply won't find at a standard concert hall.

Making the Most of Your Evening

Because seating is first-come, first-served, the "early bird" rule is gospel here. Doors open at 5:00 pm, and with a 7:30 pm start time, you have a generous window to explore the gardens, grab a drink from the al fresco bars, and stake out a prime spot. If you are heading to the area early, consider grabbing a pre-show dinner in the nearby Annex or Wychwood neighbourhoods. Both are just a short drive or a brisk walk away and offer a fantastic array of independent eateries that are far more interesting than standard downtown fare.

Good to Know

* **Logistics:** Entrance is strictly through the East Gate. Don't wander to the main tourist entrance; you’ll only be doubling back. * **Seating Strategy:** If you are attending with a group, ensure at least half your party is present to hold your space. Because seating is not guaranteed, arriving closer to 5:00 pm than 7:00 pm is highly recommended. * **Parking:** On-site parking is limited and costs $20. If the lot is full, the George Brown College parking lot just south of the castle is your best bet. Alternatively, the Dupont subway station is a pleasant 10-minute walk away—a great way to avoid the post-show traffic jam. * **Weather:** This is a rain-or-shine event. While the pavilion offers cover, the gardens can get cool once the sun goes down, so bring a light layer. * **Accessibility:** If you or a guest require accessible seating, call 416-923-1171 well in advance. The staff at Casa Loma are well-versed in accommodating guests in the pavilion, but they need notice to ensure you have the best view in the house.

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