Leaside After Dark: 5 Fun Things to Do at Night

Leaside is easy to think of as a daytime neighbourhood, but there is plenty to do once dinner is over.

You can catch live jazz on Bayview, play pickleball or padel late into the evening, lace up for a skate or even turn curling into a group night out.

Here are five ideas for the next time you want to do something more interesting than heading straight home.

1. Play Pickleball or Padel at Fairgrounds Leaside

At 849 Eglinton Avenue East, Fairgrounds Leaside has 11 pickleball courts and four padel courts, along with a lounge, food and drinks, ping-pong and a sauna.

The facility stays open until 11 p.m. Monday through Saturday and 10 p.m. Sunday, making it one of the easiest late-evening activities in the area.

You can book a court, join open play, take a lesson or try one of the club's weekly social sessions.

Best for: Dates, groups of friends and anyone who likes a little competition.

2. Catch Live Jazz on Bayview

The Leaside Live Jazz Series returns to Bayview on Friday, November 27, 2026 at 1522 Bayview Avenue.

Doors open at 7 p.m., with the show beginning at 7:30 p.m. The evening features emerging vocalists alongside The Fat Quarter Ensemble in an intimate listening-room setting.

Dinner packages and shared-table options are also available, so it can work as a full evening rather than just a quick concert stop.

Best for: Date night, music fans and a quieter evening out.

3. Go for an Evening Skate at Leaside Memorial Gardens

Leaside Memorial Community Gardens Arena at 1073 Millwood Road operates an indoor rink and is currently listed by the City of Toronto as open.

Drop-in skating schedules change throughout the season, so this is one activity where checking the City schedule before leaving matters.

A casual skate can be an easy option when you want to get out for an hour without committing to an entire night.

Best for: Families, couples and a low-key winter evening.

4. Try Curling With a Group

Right next door, Leaside Curling Club at 1075 Millwood Road has eight sheets of curling ice and operates from September through April.

The club rents ice to individuals, companies and groups from mid-November through mid-April, and no previous experience is required. Instructors can also be arranged.

That makes curling a more realistic casual-night option than many people probably realize.

Best for: Groups, work outings and trying something different.

5. Build a Bayview Night Around Dinner and a Show

Sometimes the activity does not need to be complicated.

Start with dinner along Bayview Avenue, then pair it with live music, dessert or one of the neighbourhood's evening events.

When the Leaside Live Jazz Series is running, the combination is especially easy: dinner and music are already happening in the same Bayview setting.

Best for: An easy date night without driving across the city.