HomeNews & LifestyleThe Pilot In Toronto Offers Casual Fun Alongside Amazing Outdoor Dining

The Pilot In Toronto Offers Casual Fun Alongside Amazing Outdoor Dining

One Of Toronto’s Iconic Roof Top Bars

The Pilot is a historic rooftop bar located in the Yorkville neighbourhood of Toronto, Canada. The bar has been in operation since 1944 and has become a beloved institution among locals and visitors alike.

The Pilot’s rooftop patio offers stunning views of the city skyline and is a popular spot for after-work drinks, weekend brunch, and summer cocktails. The bar is also known for its live music performances and has hosted many well-known artists over the years.

What sets The Pilot apart from other rooftop bars in Toronto is its history and character. The building that houses the bar was built in 1914 and was originally a Victorian-era row house. The bar has been carefully preserved and restored, with much of the original woodwork and decor still intact.

In addition to its rooftop patio, The Pilot also has several other areas for guests to enjoy, including a cozy indoor bar and a spacious dining room. The menu features classic pub fare, as well as more upscale dishes like steak and seafood.

Overall, The Pilot is a must-visit spot for anyone looking for a unique and memorable rooftop bar experience in Toronto.

The Pilots History

the pilot toronto
image: @thepilot_to on Instagram

The Pilot rooftop bar has a rich history that dates back to 1944 when it first opened its doors. The building that houses the bar was originally a Victorian-era row house built in 1914, and it was converted into a bar in the 1940s.

The bar was named after a Royal Canadian Air Force training program called the British Commonwealth Air Training Plan, which was commonly referred to as “The Pilot Plan.”

In the early days, The Pilot was a popular spot for pilots and aviation enthusiasts, who would gather to swap stories and enjoy a drink or two. Over the years, the bar became a favourite haunt of artists, musicians, and writers, and it played a significant role in the cultural scene of Toronto.

In the 1970s, The Pilot was threatened with demolition, but a group of local residents and artists came together to save the building and preserve its historic character. The bar underwent a significant renovation in the 1990s, which included the addition of the rooftop patio and the restoration of many of the building’s original features.

Today, The Pilot is a beloved institution in Toronto and a popular destination for locals and visitors alike. It continues to be a hub of artistic and cultural activity, and it remains true to its roots as a gathering place for pilots and aviation enthusiasts.

Where Is The Pilot Located?

the pilot toronto
image: @thepilot_to on Instagram

The Pilot rooftop bar is located at 22 Cumberland Street in Toronto. It’s situated on the 3rd floor of The Pilot Tavern, which is an historic pub located in the city’s Yorkville neighbourhood.

If you are using public transportation, you can take the subway to the Bloor-Yonge station and walk about 5 minutes to reach The Pilot Tavern. If you prefer to drive, there are several paid parking lots in the area.

Here are some driving directions to The Pilot Tavern from the downtown core of Toronto:

  1. From downtown, head north on Yonge Street.
  2. Turn right onto Cumberland Street.
  3. The Pilot Tavern will be on your left-hand side, just past Bellair Street.

Alternatively, if you are using a ride-sharing app or taxi, you can simply input the address of The Pilot Tavern into your preferred app, and it should give you directions that’ll drop you off right in front of this popular rooftop bar.

Does The Pilot Have A Dress Code?

the pilot toronto
Image: @thepilot_to on Instagram

While The Pilot likely had a dress code back in the day, you don’t have to worry about one now, per se.

The vibes here are casual, but of course you want to carry through your personal brand consistency and dress for success wherever you go. Who knows, you might bump into a pilot and those gals are notoriously well-dressed.

What Food Does The Pilot Serve?

the pilot toronto
Image: @thepilot_to on Instagram

The Pilot rooftop bar serves a variety of delicious food, including appetizers, entrees, and desserts. The menu features a mix of classic pub fare and contemporary cuisine, with an emphasis on fresh, locally sourced ingredients.

Some popular appetizers on the menu include nachos, poutine, calamari, and bruschetta. For entrees, guests can choose from a selection of salads, sandwiches, burgers, and main courses such as fish and chips, steak frites, and roasted chicken. Vegetarian and gluten-free options are also available.

In addition to their food menu, The Pilot rooftop bar also has a selection of cocktails, beer, wine, and spirits. Guests can enjoy a cold beer or a handcrafted cocktail while taking in the stunning views of the Toronto skyline.

Overall, The Pilot rooftop bar’s menu is designed to cater to a variety of tastes and preferences, with something for everyone to enjoy. Whether you’re looking for a quick bite or a full meal, you’re sure to find something delicious at this popular Toronto establishment.

What Else Is The Pilot Known For?

the pilot toronto
Image: @thepilot_to on Instagram

The Pilot rooftop bar is not only known for its great food, drinks, and stunning views of Toronto, but it is also known for its support of the LGBTQ+ community and involvement in Toronto Pride.

During Pride time, The Pilot rooftop bar has been known to host special events and parties to celebrate the LGBTQ+ community. In past years, they have hosted drag shows, dance parties, and other events featuring local LGBTQ+ performers and artists.

Additionally, The Pilot rooftop bar has been a sponsor of Toronto Pride and has shown its support for the LGBTQ+ community through various initiatives and partnerships. This has included donating a portion of sales to LGBTQ+ charities and organizations, hosting fundraisers and benefit events, and partnering with other local businesses and groups to promote LGBTQ+ inclusion and visibility in Toronto.

Overall, The Pilot rooftop bar is a beloved establishment in Toronto’s LGBTQ+ community, known for its welcoming and inclusive atmosphere, delicious food and drinks, and commitment to supporting and celebrating the diverse communities of Toronto.

Private Events

the pilot toronto
Image: @thepilot_to on Instagram

Book a private event at The Pilot rooftop bar in Toronto! It’s a great way to celebrate a special occasion with friends, family, or colleagues. The rooftop bar is available for private events. This includes birthday parties, corporate events, weddings, and other special occasions.

To book a private event at The Pilot rooftop bar, you can contact the bar to discuss your requirements and their availability. They will work with you to create a custom event package. Because of this, it will suit your needs and budget. You can choose to include food and beverage options, event space rental, and any other additional services you may require.

The rooftop bar can accommodate up to 200 guests. You can also configure the space to suit a range of event types, from casual cocktail parties to formal sit-down dinners. The bar’s events team can assist with event planning and logistics, including decorations, audiovisual equipment, and entertainment.

The Pilot rooftop bar also offers a variety of event menus, including appetizers, entrees, and desserts, with vegetarian and gluten-free options available. Guests can also choose from a selection of cocktails, beer, wine, and spirits to suit their tastes and preferences.

Overall, booking a private event at The Pilot rooftop bar is a great way to celebrate a special occasion. It’s a unique and memorable experience in one of Toronto’s most iconic rooftop bars. What else is there to say?

Saturday Jazz

the pilot toronto
Image: @thepilot_to on Instagram

The Pilot rooftop bar in Toronto hosts a weekly Saturday Jazz event. This spot is a popular attraction for locals and tourists alike. The event features live jazz music from local musicians along with delicious food and drinks, and stunning views of the Toronto skyline.

The Saturday Jazz event typically starts in the afternoon and continues into the evening. The jazz musicians perform on the rooftop bar’s outdoor patio. This provides a relaxing and intimate atmosphere for guests to enjoy. The music ranges from classic jazz standards to contemporary interpretations.The musicians also often interact with the audience and take requests!

In addition to the live music, guests can enjoy a variety of food and drink options from The Pilot’s menu. These include appetizers, entrees, and desserts, as well as a selection of cocktails, beer, wine, and spirits. The rooftop bar also offers a special Saturday Jazz menu. Here you’ll find a selection of jazz-inspired cocktails and dishes.

Overall, Saturday Jazz at The Pilot rooftop bar is a great way to spend a relaxing afternoon or evening. You’ll enjoy great music, delicious food and drinks, and stunning views of the city. Jazz aficionados and those simply looking for a unique and memorable experience… don’t miss Saturdays at The Pilot!

Related: Check out our article on the best jazz bars in Toronto

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