More than 50 free events coming to Windsor through new summer and fall series

The Experience Windsor series launches in Windsor, Ont., on Tuesday, June 16, 2026. (Sanjay Maru/CTV News Windsor)

Windsor will play host to more than 50 free events and activities this summer and fall as the city launches a new initiative aimed at making local entertainment more affordable.

The Experience Windsor series will feature waterfront festivals, neighbourhood celebrations, movie screenings, roller-skating nights and opportunities to swim, skate, curl and golf at municipal facilities.

The initiative, approved by city council in late May, is supported by up to $500,000 from the city’s Tourism Development, Infrastructure and Program Reserve. The reserve is funded through the municipal accommodation tax collected from hotel stays and must be used for tourism-related purposes, according to Windsor Mayor Drew Dilkens.

“We know that this is going to be a challenging summer for families to afford to be able to fly or get into a long road trip,” said Dilkens. “They’re going to want to stay home and stay local.”

Experience Windsor is divided into three programming streams: the Riverfront Summer Series, Staycation Activation and Neighbourhood Nights.

The Riverfront Summer Series will include four themed festivals:

• Riverfront Rewind at Reaume Park on July 11.
• The Big Picnic at Alexander Park on July 25.
• Riverfront Speakeasy at Michael D. Hurst Legacy Park on Aug. 22.
• Great Canadian Riverfront at Dieppe Park and Gardens on Sept. 6.

Each festival will transform a different waterfront park into a free destination featuring entertainment, food and interactive activities.

“Because one of our best natural attractions is our riverfront,” Dilkens said.

The Staycation Activation stream will use civic, recreational and cultural spaces for events running from June through October.

Among them are free Saturday movie screenings presented in partnership with the Windsor International Film Festival.

Films will be shown at the Windsor Armouries on July 4, 11, 18 and 25, before moving to the Capitol Theatre on Aug. 1, 8, 15, 22 and 29.

WIFF executive director and chief programmer Vincent Georgie said families will also receive free popcorn and drinks at the screenings.

“I really can’t wait for the Saturday screenings downtown,” said Georgie. “So every Saturday of July and August, you’ve got a free family film at the Capitol Theatre and at the Armouries.”

The planned lineup includes The Little Mermaid, The Wild Robot, The Lego Movie and The Lion King.

For Georgie, the value of the screenings extends beyond giving families something inexpensive to do.

“So many kids are in the house. Where are they watching movies? Maybe on an iPad in the basement,” he said. “So watching a fantastic film is one thing, but watching it in a beautiful space such as the Capitol Theatre or the Armouries, I think, actually makes memories.”

The new programming will run alongside Windsor’s established festivals and seasonal activities. For example, the Saturday screenings will be shown at times that will complement the Downtown Windsor Farmers’ Market.

“We’ll start right at 11 o’clock in the morning for the films, so some families will have already been to the farmer’s market or some can go after. We wanted that to be synergistic,” said Georgie.

He said that same approach guided discussions between the city, WIFF and the other organizations involved in the series.

“That was actually the core of this whole thing: how do we build on what’s already working and just make it that much better for everybody?” Georgie said.

WIFF will also partner with the city for four “dive-in” movie experiences at Adventure Bay and Lanspeary Outdoor Pool.

The screenings are scheduled for Aug. 7 and 9 at the Windsor International Aquatic and Training Centre and Aug. 14 and 16 at Lanspeary.

Georgie said the concept puts a new spin on the outdoor screenings WIFF has previously organized.

“We have a history doing drive-ins. This is a dive-in series,” he said. “We’ve got some special screenings … around some water-themed films like Jaws and Finding Nemo that we think will be a lot of fun.”

Exact capacities for the pool screenings have not yet been finalized. Georgie said residents should watch for registration information once the remaining details are announced.

“We want as many people as possible to safely enjoy it,” he said. “You can be in the pool and make a few laps, but also watch the film. I think that’s a way of making something truly an experience.”

Other Staycation Activation events include roller-skating nights at City Hall Square on July 3, 10, 17 and 24, along with the Windsor Pizza Festival on Sept. 19.

Free swimming, skating, curling and golf opportunities will also be offered at several city-owned facilities.

The Neighbourhood Nights stream will bring one free event to each of Windsor’s 10 wards throughout June, July and August. The events will feature live music, food vendors, family entertainment and local activities.

Dilkens said that portion of the series is intended to make the programming accessible beyond the downtown and waterfront areas.

“This is actually bringing the party to your neighbourhood, to be able to celebrate community and celebrate Windsor,” he said.

The first Neighbourhood Night is scheduled for June 25 at Optimist Memorial Park in Ward 4. Other events will be held at Bruce Park, Central Park, Mic Mac Park, Ford Test Track, Captain Wilson Park, Remington Park, Forest Glade Park, Realtor Park and Fontainebleau Park.

Although the reserve contained enough unallocated funding to support the 2026 initiative, the mayor said future municipal accommodation tax revenue has other demands placed on it.

“A lot of the money’s already allocated for future spending, like the Peace Fountain as an example,” said Dilkens. “We’re able to do that because that actually leads into what Tourism Windsor Essex promotes.”

More programming details, registration information and schedules are available online.