Windsor Mayor Drew Dilkens and Guests Unveil Details for the Experience Windsor Summer and Fall 2026 Event Series

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Over 50 Free Events and Activities to Showcase the Best of Windsor

Building on a commitment to creating a more vibrant, connected, and livable city while reflecting affordability challenges Canadians are facing, Windsor Mayor Drew Dilkens today unveiled the Experience Windsor event series. The new Council-approved city-wide initiative will deliver more than 50 free events, activities, and experiences across Windsor throughout the summer and fall of 2026.

Through three distinct programming streams — Riverfront Summer Series, Staycation Activation, and Neighbourhood Nights — Experience Windsor will bring parks, waterfront spaces, neighbourhoods, community centres, cultural venues and civic facilities to life with a season-long calendar of low-barrier events, entertainment, recreation, and community programming.

Joining Mayor Dilkens for the event announcement were members of City Council; Tourism Windsor Essex Pelee Island (TWEPI) and Invest WindsorEssex Chief Executive Officer (CEO) Gordon Orr; TWEPI Vice-President of Marketing and Communications Jason Toner; Executive Director and Chief Programmer of the Windsor International Film Festival (WIFF) Vincent Georgie; representatives from LiUNA!; Ward 3 Councillor Renaldo Agostino; Downtown Windsor Business Improvement Association (DWBIA) Board Chair Chris MacLeod; members of City administration; and community partners working to help bring the initiative to life.

Approved by Windsor City Council in May, Experience Windsor is supported through an investment of up to $500,000 from the Tourism Development, Infrastructure and Program Reserve — a non-taxpayer-funded reserve strictly allocated for tourism initiatives in Windsor.

As household costs rise in response to global economic uncertainties, the tariff and trade war with the United States, and conflicts in Iran, and as more families look for affordable ways to spend time together, Experience Windsor aims to provide opportunities for residents to connect with their community, explore, and discover City spaces and amenities, support local businesses, and create lasting memories throughout the season.

Mayor Dilkens said the true success and impact of Experience Windsor will be measured by the memories residents create together throughout the season.

"My hope is that every resident finds at least one Experience Windsor event that excites them — and then discovers several more," said Mayor Dilkens. "I hope families fill our parks, neighbours meet neighbours, children create memories they'll remember for years, and residents proudly share their experiences with friends and family. Windsor has incredible parks, facilities, artists, organizations, businesses, and community partners. Experience Windsor is about bringing those strengths together to create a season filled with connection, pride, and unforgettable moments."

All Experience Windsor engagement opportunities will be delivered through three distinct programming streams:

Riverfront Summer Series:

The Riverfront Summer Series will feature four signature events taking place from June through September along Windsor's internationally recognized waterfront. Inspired by Windsor's history, culture, and community spirit, each event will transform a riverfront park into an immersive destination featuring unique themes, live entertainment, interactive activities, curated food experiences, and welcoming gathering spaces. Admission will be free of charge to everyone. The 2026 Riverfront Summer Series includes the following:

  • Riverfront Rewind:
    • Reaume Park — Saturday, July 11
  • The Big Picnic:
    • Alexander Park — Saturday, July 25
  • Riverfront Speakeasy:
    • Michael D. Hurst Legacy Park — Saturday, August 22
  • Great Canadian Riverfront:
    • Dieppe Park and Gardens — Sunday, September 6

Together, the four events will create memorable seasonal experiences while celebrating the stories, traditions, and character of Windsor's waterfront.

Staycation Activation:

The second stream of Experience Windsor focuses on activating civic and cultural facilities and spaces through a coordinated series of accessible cultural, educational, entertainment, wellness, and community experiences. Running from June through October, events in this stream are designed to showcase Windsor's impressive collection of civic facilities and outdoor spaces while encouraging residents and visitors to explore and enjoy new areas. Residents can look forward to signature events including the following:

  • City Cinema Saturdays in partnership with WIFF:
    • Windsor Armouries — July 4, 11, 18, 25
    • Capitol Theatre — August 1, 8, 15, 22, 29
  • Wheels Roller Nights at City Hall Square in partnership with the DWBIA:
    • City Hall Square — July 3, 10, 17, 24
  • Dive-In Movie Experiences presented in partnership with WIFF:
    • Windsor International Aquatic and Training Centre — August 7 and 9
    • Lanspeary Outdoor Pool — August 14 and 16
  • Windsor Pizza Festival:
    • City Hall Square — September 19

Residents will also have opportunities throughout the season to enjoy free swimming, skating, curling, and golf at a variety of municipal facilities, including the following:

  • Atkinson Park
  • Capri Pizzeria Recreation Complex
  • Central Park
  • City Hall Square
  • Gino and Liz Marcus Community Complex Pool
  • Lanspeary Park
  • Mic Mac Park
  • Remington Booster Park
  • Riverside Centennial Pool
  • Roseland Golf Course
  • WFCU Centre
  • Windsor International Aquatic and Training Centre presented by WFCU Credit Union

Neighbourhood Nights:

The third stream of Experience Windsor brings entertainment, culture, and community celebrations directly into Windsor neighbourhoods. The city-wide series will feature ten free weeknight events — one hosted in each ward — throughout June, July, and August. Featuring live music, food vendors, family entertainment, and local activities, Neighbourhood Nights is designed to create welcoming gathering opportunities close to home while encouraging residents to reconnect with the parks and public spaces, and fellow residents that help define their neighbourhoods. Neighbourhood Nights will take place at the following locations:

  • Ward 1
    • Central Park — Tuesday, July 14
  • Ward 2
    • Mic Mac Park — Thursday, July 16
  • Ward 3
    • Bruce Park — Tuesday, June 30
  • Ward 4
    • Optimist Memorial Park — Thursday, June 25
  • Ward 5
    • Ford Test Track — Sunday, July 26
  • Ward 6
    • Realtor Park — Wednesday, August 26
  • Ward 7
    • Forest Glade Park — Tuesday, July 28
  • Ward 8
    • Fontainebleau Park — Friday, August 28
  • Ward 9
    • Captain Wilson Park — Tuesday, August 4
  • Ward 10
    • Remington Park — Thursday, August 6

In addition to the Experience Windsor events, as previously announced, residents are also invited to attend the Windsor Soccer Festival watch party on June 18 and 19 at City Hall Square.

Additional event details, programming announcements, schedules, and locations will be released in the coming weeks as Experience Windsor continues to take shape. To stay informed, explore www.VisitWindsorEssex.com/ExperienceWindsor for updates and the latest information on events taking place throughout the season.

For more information on City projects and services, visit CityWindsor.ca or contact 311.

Quotes:

"With a focus on Investing Responsibly, Windsor’s 2026 budget keeps affordability top of mind while ensuring the services and quality of life experiences that Windsorites deserve. Experience Windsor will provide more than 50 free opportunities for residents to explore, connect, and be entertained in their own city. Whether you are looking for live music, family activities, outdoor experiences, sporting opportunities, or places to relax with friends, there will be something for everyone. From major waterfront festivals and neighbourhood celebrations to free swimming, skating, curling, and golf opportunities, residents in every ward will have access to quality experiences that highlight the people, places, and amenities that make Windsor such a great place to live. Families are facing higher costs for almost everything right now, from gas to groceries, and many people are making difficult decisions about vacations and entertainment. We wanted to create something that gives residents exciting reasons to spend more time in their own community while still enjoying the kind of experiences that make this time of year special." 
- Windsor Mayor Drew Dilkens

"The Staycation Activation stream of Experience Windsor is about opening our doors wider than ever before. Windsor is home to world-class facilities, parks, recreation centres, and cultural venues that many residents may not have had the opportunity to fully experience. This initiative creates new ways for people to discover those spaces, try new activities, connect with their community, and take advantage of the incredible public assets available right here in their own city."
- Michael Chantler, Commissioner, Community Services, City of Windsor

"Windsor continues to build a reputation as a destination that offers authentic experiences, vibrant neighbourhoods, exceptional amenities, and an outstanding quality of life. Experience Windsor provides an exciting opportunity to showcase the best of our city to residents and visitors alike while supporting local businesses, attracting tourism activity, and reinforcing why Windsor is a great place to visit, invest, and call home. The initiative also highlights many of the places and partners who were recognized this year as part of the 11th Annual Best of Windsor-Essex Awards." 
- Gordon Orr, CEO, Tourism Windsor Essex Pelee Island and Invest WindsorEssex

"Windsor is a city that thrives when people come together. Experience Windsor is all about creating those moments — giving residents new reasons to explore, connect, and celebrate their city. Whether you're enjoying a free movie with family and friends, discovering a neighbourhood event or spending time on the waterfront, these experiences help strengthen the sense of pride and belonging that makes Windsor such a special place. WIFF is proud to partner with the City of Windsor to help bring accessible, memorable experiences to residents throughout the season."
- Vincent Georgie, Executive Director and Chief Programmer, WIFF

"My invitation is simple: come for the event, stay for the experience. Downtown Windsor will be home to several Experience Windsor activities this summer, and while you're here, I encourage you to explore everything the core has to offer. From great restaurants and patios to unique local businesses and attractions, there's always something happening downtown."
- Councillor Renaldo Agostino, Ward 3, and DWBIA Board Member

"LiUNA!625 has always believed that strong communities are built not only through construction but through connection. Whether we're supporting local charities, investing in health care, or volunteering for important causes, our commitment to Windsor extends well beyond the jobsite. Experience Windsor is a great example of the kind of initiative that brings people together and encourages residents to enjoy the community we've all helped build. We are proud to be the presenting sponsor of the Riverfront Summer Series and help make these free waterfront events accessible to everyone. As an organization rooted in the values of hard work, community, and pride of place, we're honoured to help bring the Labour Day weekend finale to life."
- Rob Petroni, Business Manager, LiUNA!625

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