Like bold reds & blue skies or county sights & city lights - a road trip in Windsor Essex goes better when we do it together!

Start planning your own road trip now to Windsor Essex using our Official Visitor Guide. Flip through the guide for info & tips on the best things to see & do in Windsor Essex - then head out and explore! And take your pics while you're doing it!

Enter today for your chance to Win 1-of-3 Staycation Experiences in Windsor Essex and plan a trip together with your family or loved one or someone special in your life, pairing some of the greatest things to do in Windsor Essex together. Your staycation experience will give you the best places to eat, drink, stay, shop & play!

Drop your info below and pick which road trip experience you would like to win:

• a Windsor road trip with an overnight stay at Caesars Windsor
• an Essex County road trip with an overnight stay at The Grove Hotel
• a Pelee Island escape with an overnight stay at The Wandering Dog Inn

To be a valid entry you must register for at least ONE Tourism Windsor Essex digital passport. For more details or to register for a pass today (most are free) click visitwindsoressex.com/wegotogether.

Snap & Share to Win a Windsor Essex Staycation

Grand prize draw to occur on November 1st at approximately 12pm. One grand prize draw with an approximate value of $500 retail value to be awarded to be taken by June 30th, 2025. No cash value. Non-transferrable. Must be 19+ to enter.

By submitting your photo you grant Tourism Windsor Essex Pelee Island permission to use on their social media channels, website and/or in advertising elements.