Windsor Essex with Kids: The Most Surprising Weekend Getaway
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As a kids travel content creator, my kids and I have been to some pretty incredible places around the world this year, but somehow Windsor Essex – just 20 minutes from Detroit and four hours from both Toronto and Chicago – ended up being the most surprising trip of all. What I thought would be a quiet agricultural weekend turned into one of our favourite family getaways, filled with wineries, breweries, farms, quirky shops, and some of the most charming small towns in Ontario.
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Open Farms Day
Our visit happened to line up with Open Farms Day, a once-a-year event where 16 local farms open their gates for families to explore. It’s designed to give visitors a real look at where our food comes from, with tractor rides, tastings, animal encounters, and hands-on activities for kids.
We fueled up with strong java from micro-roastery Acorn & Oak Coffee before heading over to Sauvé’s Country Market. The kids climbed onto a tractor ride through the fields and forests, ran through a spooky corn maze complete with giant skeletons, and giggled as they “milked” a mechanical cow. Meeting the (real) cows was the highlight, but they also loved pushing mini shopping carts inside and picking out their own local treats while we stocked up on farm fresh produce. This first stop set the tone for how special Open Farms would be.
Next was Trimble Farms Cattle Company, a working cattle farm focused on field-to-fork. Here the kids collected fresh eggs, met the herd, and learned how the cows are raised without antibiotics or hormones. At Raymont’s Berries, we filled baskets with ripe raspberries straight from the vine, then made a quick stop at Denver’s Homestead to say hello to the chickens and let the kids jump on the bouncy castle set up for the event. From there it was on to Hawksview Honey, where we met the beekeepers and left with jars of golden honey.
Wineries on Lake Erie’s North Shore
After a full morning on the farms, we spent the afternoon exploring some of the wineries along Lake Erie’s North Shore. There are more than 20 wineries in the region, and what surprised me most was how family-friendly they all are. At Vivace Estate Winery, we ordered a full charcuterie board piled high with local meats and cheeses. The kids had fun roaming around and catching grasshoppers, while we enjoyed a fantastic wine tasting flight. Muscedere Vineyards was just as fun, but with a completely different vibe. There were goats and chickens to visit, a small playground, wood-fired pizza, and a gelato stand serving flavours like Nutella and Bounty. These wineries struck the perfect balance: relaxed enough for kids to play, while parents got to enjoy really great wine and food.
Breweries in Windsor Essex
Windsor Essex is also home to more than a dozen breweries and our final stop of the day at GL Heritage Brewing Company ended up being one of the most fun parts of the weekend.
Because we visited during Open Farms Day, the brewery had turned its big outdoor space into a full family festival. The kids rode ponies, visited donkeys, and bounced between lawn games and craft tables. Even outside of the event, GL Heritage has a reputation for being one of the most family-friendly breweries in the region.
My husband ran out to grab a Windsor-style pizza to-go from OG Pizza Harrow for our picky eaters, while we tucked into some of the best Brussels sprouts from the onsite food vendor and shared flights of craft beer and hard seltzers. GL Heritage has a great story behind the brand and a creative approach to brewing fun flavours like the spicy pineapple Ca-Jen Pale Ale. The best part? GL Heritage was just a five-minute walk from where we were staying.
Where We Stayed
For our home base, we checked into the Little White Church Boutique Hotel. Built in 1892 and beautifully restored, this converted church was a unique place to stay. Stained-glass windows and soaring ceilings gave it a lot of character, but it was also very functional for a family stay. The kids had a loft with a cool staircase to climb up to their own second-floor space with two beds, there was a small kitchenette with a microwave for snacks, and plenty of room for everyone to spread out after long days exploring.
Charming Towns, Shops & Family Fun
The rest of the weekend was all about quirky, kid-friendly experiences that made Windsor Essex feel so unique. Everyone’s favourite stop was hands down Ure’s Country Kitchen. This roadside diner is so much more than it looks: part convenience store stacked with treats, part old-school ice cream parlour with 30+ flavours, and even a gas station. Their homemade cinnamon-sugar donuts are worth the stop alone, and the breakfast sausages were the best we’ve ever had. Out back is where it really shines though – a botanical-themed mini golf course with ponds, fountains, trick shots, and a 16th-hole waterfall dump that had the kids squealing (don’t forget to bring a towel!).
We also stopped at John R. Park Homestead, which turned out to be way more fun than I expected. The kids pressed apples into cider, tried old-fashioned toys, tasted pumpkin bread cooked over an open fire, fed goats, and wandered through the heritage buildings while costumed interpreters brought the 1800s to life. The highlight for my son was catching a toad in the sawmill, which he still swears was the best part of his weekend.
For downtime, Colchester Beach and Harbour was perfect. The sand is soft, the water is clean, and there’s a giant pirate ship playground and splash pad. It gave the kids a chance to run wild while we caught our breath.
Billy’s Taphouse was another foodie standout. Everything on the menu is homemade with fresh, local ingredients, and nothing is processed. They brew their own craft beer, grow herbs in their garden out back, and even have a full sand volleyball court that kids are welcome to play in when it’s not in use.
To round out the trip, we explored Amherstburg, one of the most picturesque towns in the region. With waterside benches, cozy coffee shops, and even an old-school candy store, it oozes charm. We popped into River Bookshop with its fantastic children’s section and coincidentally stumbled upon their weekly storytime in the art alley surrounded by the colourful Essex Murals.
Our last stop was Priscilla’s Presents, which captured the spirit of Windsor Essex perfectly. It’s part quirky gift shop, part vintage ice cream parlour, and part cut-your-own sunflower field. The kids chased butterflies between the blooms while I browsed the shelves and swooned over the sunflower field stretching behind the shop. It summed up the region in one stop: unexpected, family-friendly, and full of charm.
Final Thoughts
By the time we headed home, I couldn’t believe Windsor Essex hadn’t been on our radar sooner. Between the farms, wineries, breweries, beaches, and small-town gems, it turned into one of the most family-friendly trips we’ve taken all year. This is a hidden gem that deserves way more attention.
Original Blog Post By: Olga Valentin, Mini Jetsetter
