Playgrounds, Parks and Good Food: Our Family Getaway in Windsor
Four days of waterfront paths, family adventures and a bike ride into Detroit.
For us, a family getaway needs a few things: somewhere to ride, time outside, good food and places for Lilly to play.
Windsor gave us plenty of all four.
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In early October, Adam, Lilly and I packed up the car, brought the bikes and headed to Windsor, Ontario. It was about a four-hour drive from home. Over the next few days, we explored waterfront paths, stopped at playgrounds, walked through parks and worked our way through some great places to eat. We even rode our bikes across the Detroit River for a day of exploring on the other side.
Travelling with Lilly adds a different pace to our adventures. There’s the ride itself, and then there’s the playground along the way. There’s a walk through a park, with plenty of reasons to stop and investigate something small. Those moments were a big part of this trip.
We stayed at Hyatt Place Windsor, our base for all four days. From there, we had a mix of outings across Windsor and a cycling adventure into Detroit, with time together at the centre of it all.
If you’re looking for things to do in Windsor, Ontario, with kids, here’s what filled our four days.
Windsor’s Waterfront Paths and Playground Stops
After the drive, our first outing was a walk along the Herb Gray Parkway Trail. Getting outside and moving around was a good way to settle into the trip.
The waterfront became another part of our exploring. Along the Windsor Riverfront Trail, we could ride beside the Detroit River, take in the views across the water and make stops along the way.
One of those stops was the pirate ship playground. With Lilly along, playground time was very much part of the outing, and having places to stop and play added to the fun of being out on the bikes together.
We also explored Windsor Sculpture Park, where the outdoor artwork gave us more reasons to slow down and look around. There’s something nice about discovering a city this way, moving between the paths, public art and open spaces at your own pace.
Our waterfront exploring also included a stop at the Hiram Walker Statue.
For a family outing, the riverfront gives you plenty to work with. Pick a stretch to ride or walk, leave room for a playground stop and see what catches your attention along the way.
Cycling from Windsor to Detroit
One of the bigger adventures of the trip was cycling across the Gordie Howe International Bridge. Check out bikethebridge.ca for everything you need to plan your own adventure.
With Lilly along for the ride, we pedaled over the Detroit River on the bridge’s dedicated multi-use path. Being on a bike gives you time to take in the views and appreciate the scale of what you’re crossing. It was a memorable way to begin a day of exploring Detroit together.
Once across, we spent time in Mexicantown, taking in the colourful murals and stopping for tacos. Lunch and some time off the bikes made a good break before heading to the waterfront.
At Ralph C. Wilson, Jr. Centennial Park, the giant bear-shaped slide in the Delta Dental Play Garden is hard to miss. We made time for Lilly to explore the play area and for all of us to enjoy the park.
The combination worked well for our family: a bike ride, somewhere new to explore, a lunch stop and plenty of time to play.
Back in Windsor, we finished the day with dinner at The GOAT Tap & Eatery in Walkerville and a stop at Frost Ice Cream Co. in South Windsor.
If you’re planning a similar ride, check the bridge’s official information for current path access, permitted bikes and travel-document requirements for everyone in your group. Allow time for border processing, and plan for the climb as well as the distance.
Where We Ate in Windsor
Food was a big part of this trip, from our first pizza dinner to café lunches, cookies and barbecue. Sitting down together between outings gave us a chance to take a break and enjoy another part of the city.
Antonino’s Original Pizza in South Windsor
Our first dinner was at Antonino’s Original Pizza in South Windsor. We got a look at the pizza-making in action before sitting down to eat.
After the drive and a walk outside, sharing a pizza was a very welcome way to finish our first day. It was also a chance to try Windsor-style pizza while we were in town.
Lunch at Taloola Café in Walkerville
Another lunch stop took us to Taloola Café in Walkerville.
We spent some time together over a meal before heading back out to explore the waterfront. Having a lunch stop between the museum, bike rides and playgrounds gave us a chance to sit down and enjoy the day together.
Cookie Bar and Sawyer’s Craft BBQ in Ford City
In Ford City, we stopped at Cookie Bar and had dinner at Sawyer’s Craft BBQ.
Both are on Drouillard Road, making them easy to pair if you’re spending time in the neighbourhood. Between the cookies and barbecue, there was plenty to look forward to after a day of exploring.
Indoor Things to Do in Windsor with Kids
Our time in Windsor also included a couple of indoor stops that gave Lilly more ways to explore and play.
Hands-On Exploring at Chimczuk Museum
At Chimczuk Museum, the exhibits introduce visitors to Windsor’s history, while the Children’s Gallery and Learning Space gives younger visitors opportunities to get hands-on.
Lilly explored the interactive displays, and we got to discover a little more about the city together. It was a good addition to a trip with so much time spent outside.
Family Fun at Big Time Entertainment
We also visited Big Time Entertainment, where the arcade and glow-in-the-dark mini golf added another kind of family fun to the trip.
If you’re putting together your own Windsor family itinerary, Chimczuk Museum and Big Time Entertainment are useful stops to have in mind when you want to mix up the day or make plans around the weather.
Nature Walks at Ojibway Park and Malden Park
Our final day included more time outside, starting with a walk at Ojibway Park.
We explored on foot and let Lilly take her time investigating the little things she found along the way. Walking with a toddler gives you plenty of opportunities to notice things you might otherwise pass by.
At Malden Park, we found more trails, grassy space and another playground stop. It was a good place to spend part of our last day, with room to move around before getting back in the car.
We also stopped at Windsor Crossing Premium Outlets in nearby LaSalle, then finished with lunch at Rock Bottom Bar and Grill in historic Sandwich Towne before heading home.
A Few Days Away, With Plenty to Remember
There were some memorable experiences on this trip, especially riding across the river into Detroit. There were also lots of smaller moments that made the time away feel special: watching Lilly explore a playground, riding along the waterfront and sitting down for a meal together.
That mix was what we enjoyed about Windsor. We had places to ride, parks to explore, activities for Lilly and good food throughout the trip.
For anyone planning an Ontario family road trip, there’s plenty here to shape a few days around what your family enjoys. Leave time for the stops along the way. A playground, a walk or an ice cream together can become as much a part of the memory as anything else on the itinerary.
We came home with new places to recommend and a reminder that a few days away, close to home, can still feel like a proper reset.
Save this post for your next family getaway, and visit Tourism Windsor Essex Pelee Island to start planning your own time in Windsor.
Click here for more highlights from this trip.
Original Blog Post by: Emily Batty
