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This summer plan a Windsor Essex Road Trip – and discover the home of Canadian whisky, the Southern mainland tip of Canada, the birthplace of bubble in Canada, Canada’s best pizza, the start of the underground railroad and more.

Check out our guide below – we’ve created easy-to-download itineraries you can use when you plan to visit – or create your own (and you even have the chance to win it!). We’ve also included great trip inspiration pieces – like our blogs, our 2021/2022 Official Visitor Guide and more.


Our itineraries are the easiest way to plan a trip to Windsor Essex. Check out our suggested and pre-designed itineraries below, or create your own using our MyTrip Digital Itinerary Builder.

This week we’re featuring our arts & culture itineraries. 


Click on any of the icons below to see ALL of our suggested 1, 2 and 3 day itinerary ideas to make the most of your trip to Windsor Essex. Select an itinerary then click the ‘Download Here‘ button to explore the itinerary in three easy way – by timeline, by calendar view, or through google maps. You can export the itinerary to your phone, and the itinerary can sync with your phone to take you step-by-step and minute-by-minute to each stop.


Blogs are a great way to learn about what others have experienced when they came to Windsor Essex. Check out our top blog posts below: 

Influencer Essentials


We’re making your next Road Trip super easy – and giving you the chance to WIN your own Road Trip itinerary worth $1,000!

  1. Click here for details on how to plan your own day trip itinerary using our MyTrip digital itinerary builder.
  2. WIN your custom road trip itinerary. Just send us the link for your chance to win!


More resources to help you plan your trip to Windsor Essex: 

Additional Resources

Additional Resources

Use these resources to help plan your trip! Our top picks feature our Official Visitor Guide, promotions, offers and much more!


Yes way, Rose! Cheers to a Sunday with good friends and a good chilled bottle from @sprucewoodshores, one of the amazing @epicwineries in #WindsorEssex! #YQG #DiscoverYQG #DiscoverON #DiscoverCanada #wine #YQGstaycation #OntSouthwest #winery #roseallday ...

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What's better than a warm weekend afternoon in a vineyard with ice cold #riesling? Add on a woodfired pizza from @Muscederevineyards? #YQGstaycation #YQG #DiscoverYQG #DiscoverON #DiscoverCanada #WindsorEssex #OntSouthwest #foodie #wine #winery ...

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There's more than just bacon and eggs out at @urescountrykitchen! Start your day with a great breakfast and then head out to their awesome mini-golf course to have a round of fun times! #YQG #DiscoverON #DiscoverCanada #DiscoverYQG #YQGStaycation #WindsorEssex ...

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