Christmas Getaway to Windsor Essex
Kimberly Erin Davies, Walkaboot Travel | December 7th, 2018
Note: please contact event planners prior to visiting. Events change frequently and as this blog was posted in 2018, they may not be occurring this year. This blog should be used for inspiration, and you can check out our Holiday Event Guide for current event listings.
It’s December and you know what that means? It’s officially holiday season! I love the holidays, so it is not shocking that I would source out the best Christmas getaways in Ontario. Windsor and Essex County has so many wonderful holiday offerings throughout November and December that I couldn’t resist checking them out. From tree lightings to parades to bumping into the big guy himself, I could not have been more impressed. Check out all the fun holiday activities Windsor and Essex County has in store and why you should visit when looking for Christmas getaways in Ontario.
The Iron Kettle
(editor’s note: the Iron Kettle tree lighting no longer occurs, but you can visit the Iron Kettle Commissary for tasty treats!)
Willistead Manor Christmas Decorations in Windsor
Visiting the beautiful and historically relevant Willistead Manor, once owned by Hiram Walker’s son Edward Chandler Walker, is one of the best things to do in Windsor Ontario. The estate has been done up for the holidays in great detail. In such an affluent, uniquely designed house, there is no doubt that its Christmas decorations should be as decadent as the house itself. Put on by ‘the Friends of Willistead Manor’, preservationists and volunteers, the home is carefully curated and decorated for the holidays by interior designers and design classes from St. Clair College. With each room showcasing a specific theme, the house becomes the definition of coziness in the winter. A delight to explore.
River Lights Winter Festival in Amherstburg
Visit a town immersed in the holiday spirit!
Every night from November 15, 2025 to January 4, 2026, hundreds of customized LED light displays light up the town’s two main parks. King’s Navy Yard Park, along the Detroit River, features traditional displays that showcase the warm hearted feel of the season with carolers, angels, soldiers and more. Toddy Jones Park features whimsical, playful displays for the kids and the kid at heart to enjoy.
Epic Taste of the Season
Enjoy the spirit of the season in EPIC wine country! Discover unique gifts, delicious local wines, and cheerful festivities at each of our participating wineries!
Wineries are collecting canned goods and donations for local food banks.
Fantasy of Lights Kingsville
The Fantasy of Lights in Kingsville takes place at a public park which has been decorated with various Christmas lights and collections. Walking through the park was a pleasant experience. I loved seeing everything so lit up.
Cindy’s is one of the best Christmas Stores in Ontario
That’s right, I said it. I had a blast doing my Christmas shopping in Essex County at Cindy’s in Kingsville, and I was surprised at the size of it. There is actually something for everyone here, from delicious food to fabulous fashion to adorable nick knacks, and all things Christmas. Cindy’s even has its own Christmas Market. When considering Christmas Markets in Ontario, this would be on my list.
Windsor Essex and Pelee Island has so much going on for the holiday season. Discovering what to do in Windsor Essex is wonderfully simple as every weekend has something unique and different happening with regards to the holidays. This Canadian location is a perfect choice for Christmas getaways in Ontario Southwest.
This blog was created in partnership with funding from Ontario Southwest. To explore more that you can do in #OntSouthwest check out ontariosouthwest.com.
