Road Trips & Real Adventures: An Entertaining Escape To Windsor Essex

Road Trips & Real Adventures: An Entertaining Escape To Windsor Essex

Original blog by Carrie Steinweg

As I pulled up an online map, I was surprised to learn that from my home just outside Chicago in Northwest Indiana, I could be in another country in less than a four hour drive. I’d traveled to Ontario in the past to Thunder Bay and to Niagara Falls, which were much longer treks by car. So, when our aunt was traveling from her home in Europe to visit a friend in Kingsville, Ontario and invited us to meet her there for a few days, it seemed like a perfect opportunity to see more of this Canadian province – and there was a bonus of it being much closer than anticipated.

We made our way into Canada via the Detroit-Windsor Tunnel and spent a little time walking the riverfront in Windsor before heading to Art Windsor Essex, the largest public art gallery in Southwestern Ontario. The 15,000-square-foot gallery has a an eclectic mix of works by Canadian artists. We also explored the Chimczuk Museum, which is located in the same building and gave an interesting overview of the local history. The museum covers history of the Windsor area, including exhibits on prohibition, the Underground Railroad and the area’s agricultural significance as the “Tomato Capital of Canada.”

Next we made a stop at the 36-room mansion named “Willistead Manor,” which was built for one of the sons of distiller, Hiram Walker. Since we arrived just past closing, we weren’t able to tour in the interior, but it was still worth the trip to see the 15-acre estate, which is now a public park, and three buildings on the site.

Our second day was spent at Point Pelee National Park. This beautiful natural space is where you will find the southernmost point of the Canadian mainland. It’s the most ecologically diverse national park in Canada and the views are breathtaking as you make your way down the point to where it narrows to a small, sandy tip with Lake Erie surrounding you. There are several paths for walking, hiking and biking and canoe and kayak launches. Campsite and cabin accommodations are available in the park. We drove to the visitor center, which delivered us near the beach via shuttle and we walked all the way to the very end.

The following day we made our way to Historic Amherstburg, a town near the mouth of the Detroit River where Fort Malden was established in 1796. We walked around downtown, along the water and along the main street lined with beautiful, historic homes. We also explored Fort Malden Historic Site where costumed entrepreneurs roamed the grounds.

That afternoon, we visited the Canadian Transportation Museum & Heritage Village in Kingsville. Situated on a 100-acre site, you’ll find one of the largest transportation museums in Ontario as well as the only ambulance museum in Canada. The museum also includes a fun, nostalgic 1950s diner. My husband loves antique cars so when there’s a car museum nearby, we like to work that into our travels. This one did not disappoint and included car models we’d never seen before. The Heritage Village, located just behind the museum, is a collection of over 20 buildings dating from the 1700s to the 1920s.

On day four we made our way to the town of Harrow where the 169th Harrow Fair was happening. We had so much fun wandering through the exhibits of everything from flower arranging to poetry to needle arts. We sampled some home baked pies, made our way through the poultry and cattle barns, watched auctions and sat in tractors. We followed it up with a stop for ice cream and mini golf at Ure’s Country Kitchen & Mini Golf and then ate and hung out at the Polish Beach Club.

On the way home I took a little detour through Colchester so I could stop at The Grove Motel, which opened recently. I’m a big fan of the show, Schitt’s Creek, which was filmed in Ontario, and you’ll find a few nods to the show in this new retro motel. A David Rose quote is etched above a wine cooler, a key card slot bears a photo of Eugene Levy and the large painting behind the front desk resembles the one that hung in the lobby of the Rosebud Motel.

On our final day, before heading out of town we took an e-bike wine tour with Unconquered Customs Custom Electric Bike Wine Tours. The vintage-style bikes were accompanied by vintage looking helmets and goggles and set a whimsical vibe for our day. We met at the John R. Park Homestead. Included is a ticket for admission to the Homestead to use after the bike tour.

We visited three wineries where we had a flight at each location with a charcuterie board at our middle stop. It was a wonderful way to see the landscape, riding along country roads where we didn’t really do a lot of pedaling thanks to our e-bikes. Our tour guide’s sidecar stored our purchases. It was a lovely way to finish up our time in Southwestern Ontario – leisurely sipping wine on the outdoor patios, soaking up nature and reflecting on a memorable and relaxing few days in a place I never knew was just a few short hours from home.

Our time included some amazing food and drink, as well, and I’ll explore that more in another blog post.

Original Blog Post by Carrie Steinweg. Carrie is a freelance writer, photographer, author and blogger in Northwest Indiana. She writes a travel column for the Northwest Indiana Times and shares her food adventures on the blog Chicago Foodie Sisters. You can follow @chicagofoodiesisters on Instagram, TikTok and Facebook.

Sponsored story by Tourism Windsor Essex. For more details on Tourism Windsor Essex click their website, or visit them on Facebook, Twitter, or Instagram.