The Ultimate Family Weekend in Windsor Essex: 4-Day Itinerary with kids
If youโre looking for a quick, stress-free, and incredibly fun family getaway from Ottawa, put Windsor, Ontario right at the top of your list! Windsor Essex seamlessly combines rich history, beautiful waterfront trails, and an incredible food scene that welcomes families with open arms.
We recently teamed up with Tourism Windsor Essex Pelee Island for a 4-day summer adventure with our 5-year-old. Flying out of Ottawa on Porter Airlines made travel an absolute breeze. We were in the air and touching down at Windsor International Airport (YQG) in under two hours! The terminal was remarkably easy to navigate with luggage and a young child in tow. Within minutes of landing, we picked up our rental car right outside the terminal doors and were ready to begin our road trip.
Here is a look at our exact itinerary and how we fell in love with Windsorโs incredible food, waterfront views, and family-friendly spots.
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Thursday
Checking In: DoubleTree by Hilton Downtown Windsor
After a quick drive from the airport, we checked into the DoubleTree by Hilton Windsor Hotel & Suites. You really canโt beat this location! It sits right on the riverfront next to Dieppe Gardens, offering sweeping views of the Detroit skyline across the water. The rooms are incredibly spacious, giving our little one plenty of room to unwind after travel day. The best part for our 5-year-old? The warm, legendary chocolate chip cookies handed to us right at check-in!
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Dinner: The Loose Goose RestoPub & Lounge
For dinner, we took a short, pleasant walk over to The Loose Goose in downtown Windsor. Itโs a beloved local staple in the area, super welcoming for families, and famous for its wings with over 60 different sauces and rubs to choose from! The relaxed atmosphere and patient staff made dining with a young child completely stress-free. It was the perfect comfort-food meal to officially kick off our trip.
Evening Walk: Riverfront Sculpture Park & Streetcar No. 351
After dinner, we strolled along the Windsor Sculpture Park, a unique “museum without walls” featuring over 30 large-scale contemporary sculptures right along the scenic river trail. The wide paved paths are ideal for strollers or little feet that need to burn off extra energy before bedtime. We made a special stop at the Legacy Beacon to check out Streetcar No. 351, a fully restored 1918 streetcar that had our 5-year-old completely fascinated. We topped off the evening with a sweet treat at the Streetcar Cafรฉ while watching the river barges float past before heading back to our hotel.
Friday
Breakfast: The River Room Restaurant
We started our morning at The River Room, located conveniently on the 2nd floor of our hotel. Fueling up with a delicious breakfast while looking out over the Detroit skyline set the absolute best tone for the day. Their kid-friendly menu options and floor-to-ceiling windows kept our 5-year-old happily entertained while we enjoyed our morning coffee.
Morning & Lunch: Colasantiโs Tropical Gardens
By 10:00 AM, we made the 45-minute drive to Colasantiโs Tropical Gardens in Kingsville, and wow, this place is a total dream for kids! Itโs a massive 3.5-acre indoor tropical wonderland filled with cacti, exotic plants, a petting zoo, mini golf, and arcade games. Our little one had an absolute blast feeding the animals and playing games. For lunch, we dug into their famous “Broasted” chicken, fresh pizza, and their special homemade apple cider donuts that truly live up to the hype.
Afternoon: Seacliff Park & Beach (Leamington)
Just 15 minutes away in Leamington, we spent a sun-drenched afternoon relaxing at Seacliff Park & Beach along the shores of Lake Erie. Between the lengthy sandy beach, shaded green space, and the massive Tomato Splash Pad, our 5-year-old burned off tons of energy splashing around with other kids. The facilities here are exceptionally clean and accessible, making it an easy beach stop for parents traveling with young children.
Dinner: Armandoโs (Walker Rd. Location)
You cannot visit Windsor without trying authentic Windsor-style pizza, and Armandoโs is one of the best! Famous for its shredded pepperoni, canned mushrooms, and local Galati mozzarella baked to perfection, this award-winning pizza was an instant hit with our entire family. They also cater wonderfully to dietary needs with delicious gluten-free options and their own 100% vegan cheese!
Saturday
Breakfast: Downtown Windsor Farmersโ Market
We spent Saturday morning soaking in the vibrant community vibe at the Downtown Windsor Farmersโ Market. We grabbed delicious breakfast pastries from local vendors, strolled past bustling stalls of fresh local produce and handcrafted goods, and stopped by the dedicated Kids Corner. Our 5-year-old loved the hands-on craft activities and live music, making it a wonderful way to connect with the local community.
Morning: Museum Windsor – Chimczuk Museum & Art Windsor-Essex
Located just steps from the market, the Chimczuk Museum was a massive highlight for our child. While the main galleries cover fascinating local history and Indigenous culture, the state-of-the-art Childrenโs Gallery & Learning Space offers interactive exhibits, dress-up stations, and hands-on play that kept our child happily engaged for hours. Afterwards, we popped upstairs to explore Art Windsor-Essex (AWE) to appreciate incredible historical Canadian and contemporary artwork together as a family.
Lunch: Bistro At the River
Located right on Riverside Drive, Bistro at the River offers a gorgeous outdoor patio overlooking the Detroit River. We enjoyed a delicious, casual lunch in the sunshine while taking in the fresh air and watching boats cruise along the international waterway. The casual outdoor setting was very accommodating for a family with a young child.
Afternoon: Adventure Bay Family Water Park
If you have kids, Adventure Bay is a non-negotiable Windsor stop! This massive indoor water park sits right in the heart of the downtown core, making it super convenient to access. From the low-depth Tot Loch splash slides and relaxing lazy river to the gentle wave pool and multi-level Cannon Cove dry play structure, our 5-year-old was in total paradise and did not want to leave.
Dinner & Dessert: Mamo Burger & The Cookie Bar
For dinner, we headed over to the trendy Ford City neighborhood on Drouillard Road to visit Mamo Burger (operating out of the same building as Cookie Bar). Their fresh, hand-pressed craft burgers loaded with local ingredients were incredible. Afterwards, we couldn’t resist picking up a few quarter-pound, scratch-made gourmet treats from Cookie Bar for dessert for the perfect sweet ending to an active day!
Evening: Willistead Manor Park
Before wrapping up the day, we took a peaceful evening stroll through Willistead Park. Our 5-year-old had a blast running around the playground tucked into the southeast corner of the grounds while we admired the stunning historic architecture of the 1906 Willistead Manor. The sprawling, mature shade trees made it a picturesque spot for family photos.
Sunday
Breakfast: Thyme Kitchen
We kicked off our final morning in downtown Windsor with a chef-driven, locally sourced breakfast at Thyme Kitchen. Their menu caters brilliantly to all dietary preferences with gluten-free, vegetarian, and vegan choices, and their specialty coffees were top-tier. The bright, welcoming atmosphere made us feel right at home from the moment we walked through the door.
Morning Walk: Pivoting to Local Gem Shopping:
When a light drizzle settled over Windsor on Sunday morning, we pivoted our outdoor plans at Ojibway Park to support some amazing local businesses, and it turned out to be such a fun alternative! We spent the morning browsing downtown Windsor’s charming boutique shops and historic storefronts. A highlight was stopping into Whiskeyjack Boutique, a cozy shop filled with 100% Canadian-made products, local handcrafted gifts, and unique souvenirs. Our 5-year-old loved looking through all the neat local treasures and picking out a special keepsake to bring home!
Lunch: The G.O.A.T Tap & Eatery (LaSalle)
We headed to The G.O.A.T in nearby LaSalle for a relaxed Sunday lunch. It offers a super stylish, kid-friendly sports bar atmosphere with clever, elevated twists on comfort foods like gourmet burgers, crisp wings, and fresh sandwiches. The fun sports decor kept our little one entertained while we waited for our food to arrive.
Final Stop: The Velvet Scoop & Malden Park Observation Deck
Located right across the parking lot from lunch, we made one last sweet memory at The Velvet Scoop before heading home. With 32 ice cream flavors, gelatos, soft serve, and dessert treats, it was the ultimate high note to end our family trip!
As the rain cleared, we drove over to Malden Park and took the short walk(kid-friendly) up the trail to the observation platform (the highest point in Essex County!). The vantage point gave us a stunning panorama of the Detroit skyline and a front-row seat to the impressive Gordie Howe International Bridge construction project across the river.
Heading Home
With big smiles and wonderful memories, we made the quick 15-minute drive back to Windsor International Airport, returned our rental car effortlessly, and boarded our 4:30 PM Porter Airlines flight back home to Ottawa.
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Final Thoughts: Why Windsor is Perfect for Families
Windsor completely blew us away! From interactive water parks and lush tropical gardens to kid-welcoming restaurants and stunning waterfront parks, every single stop on our itinerary made traveling with a 5-year-old feel totally effortless. The warmth of the local community and the richness of the region’s family attractions exceeded all our expectations.
A huge thank you to the Tourism Windsor Essex and Pelee Island team for hosting our family and curating such an unforgettable getaway!
To see more highlight of Windsor Essex click here.
Original Blog Post by Perfectly Imperfect Fam
