Live at The Square Windsor 2026 | Free Outdoor Music | Fun Group Activities

A Different Kind of Thursday Night

Presented by the City of Windsor with support from Enbridge Fueling Futures, Live at The Square celebrates Windsor-Essex’s local music scene.

Consider it a chance to listen to someone you might not already have on your playlist. Go with an open mind, stay for a few songs and give the performance your attention. Finding a new favourite artist is a good reason to step outside your usual routine.

It is also a plan that works without a big group. Bring a friend, make it a casual date or head over on your own. There is no need to wait until everyone’s calendar lines up.

Check the City’s event page and social channels for performer announcements before choosing your evening.

Spend Some Time at City Hall Square

The plaza is more than a place to pass through on your way somewhere else.

Windsor’s redesigned City Hall Square includes a water feature, a pavilion with washrooms and gathering space intended for community events throughout the year.

Arrive a little early rather than making your entrance while trying to answer three “where are you?” messages. Agree on a meeting point, get your bearings and give yourself time to settle in.

Keep the plan simple. You do not need to fill every minute before and after the music for the evening to feel worthwhile.

Make an Evening of Downtown Windsor

Plan Dinner After the Music

Choose your dinner spot before heading out so the evening does not end with everyone standing on the sidewalk scrolling through restaurant reviews.

For an Italian option, La Guardia at 59 Pitt Street East serves pasta, pizza and other Italian dishes. Check its current menu, hours and reservation availability when planning your visit.

Leave a little breathing room between the performance and your reservation. That gives you time to walk over without spending the last few songs watching the clock.

Dinner is an optional extra, not part of the concert. Budget separately for food, drinks and transportation.

Add a Waterfront Walk

Another option is to make the riverfront part of your outing.

Windsor’s Riverfront Trail connects waterfront parks and public spaces, including Dieppe Gardens and Festival Plaza, with views across the Detroit River.

Pick a manageable section rather than setting out to cover the whole waterfront. A short walk before the music can be enough to clear your head after work. Afterwards, choose your route based on the light, weather and how much energy your group has left.

Comfortable shoes are a better companion for this plan than an ambitious step target.

Remaining dates: Thursday, September 17; Thursday, September 24; and Thursday, October 1, 2026.
Time: 5–7 p.m.
Location: City Hall Square Plaza, downtown Windsor.
Admission: Free.
Weather: Performances are weather permitting.