The Best Things to Do in Windsor, Ontario: The Ultimate Windsor Itinerary For Your Visit

Windsor, Ontario has long been a place that I’ve felt is extremely underrated in this province. If you know where to look, and how to plan your trip, you’ll be sipping on great beer and wine, feeling the breeze while out on the river (or exploring the Windsor Sculpture Park), cycling to your heart’s content, and perhaps even winning a buck or two at the casino. It’s a fun city, and worth exploring.

Walking along the Windsor Sculpture Park/Waterfront, with Detroit right across the river.

When I moved back to Canada from Istanbul a few years ago now, I hadn’t imagined that I’d visit Windsor so much, and get so much out of those visits.

I had friends who went to the University of Windsor, and they had a strong appreciation for the city, but I hadn’t really thought twice about it. When I began to visit though, I found that this with a city with passionate business owners, an epic cultural scene (the Windsor International Film Festival, street art galore), plenty of outdoor space, and neighbourhoods that each had their own flavour.

Whether you’re getting to Windsor after cycling around this area of Ontario, or heading here after trips to the beautiful destinations of Kingsville and Pelee Island, there is so much to see in this great city.

In short, I’ve found a special place in my heart for Windsor, and this article is all about sharing all I can so that you can do the same.

A Brief History of Windsor

You’ll find Windsor in Ontario’s Southwest, right on the south bank of the Detroit River. You couldn’t be closer to Detroit, in fact, if you tried. It’s population sits around a quarter of a million, but I do feel as if, for its size, it has more going on from a tourism perspective than you’d expect. But let’s back up, shall we?

Windsor's history as a settlement dates back to the late 18th century when it was originally inhabited by Indigenous Peoples. European settlement began in the late 1700s, with both French and British influences. The region's strategic location along the Detroit River made it important for trade and transportation.

In terms of the region’s indigenous history, Windsor Essex Pelee Island created a list of Indigenous Historical Sites that you may want to check out, as they aim to honour the unique histories, cultures, and contributions of First Nations, Inuit, and Metis people to this area.

Many people may not know that Windsor played a significant role in the War of 1812, with the American invasion of Upper Canada (now Ontario). Fort Malden, located in nearby Amherstburg, was a key military post during this conflict. Bri and I actually headed to Amherstburg to learn more about that history not all that long ago, and tacked on a trip to nearby Kingsville.

Windsor also has a strong connection to the Underground Railroad, was a hub for booze during the prohibition era due to its proximity to Detroit (and its impressive distilling industry), and a Canadian automative juggernaut.

Some come for the casinos, others for the distilleries and breweries, and others still to make a base to explore the emerging wine country. There’s no wrong way to approach Windsor, but there are a multitude of ways to explore this multidimensional city in Ontario.

*Please note that this post contains affiliate links. Simply put, this means that we may receive a small commission for our honest and heartfelt recommendations, at no additional cost to you.

What to Do in Windsor, Ontario

People don’t know that you could easily fill a week in Windsor, so I’d urge you to at least spend a weekend, if only to realize that, to experience it all, you’ll need to set aside another weekend or two.

Test Your Luck at Caesar’s Windsor

Whatever you think about gambling, Caesar’s Windsor is a world-class casino and hotel complex. Not long ago, my brother and I actually did a weekend away in Windsor and Detroit, and perhaps not shockingly, that’s where we stayed.

There was always a buzz, and I will say that I’ll never forget getting back from Detroit after seeing the Red Wings play our beloved (yet ever frustrating) Maple Leafs, and being able to play some roulette before bed!

Generally speaking—it offers a large casino with various games, a 5,000-seat entertainment venue, a luxury hotel, diverse dining options, a spa, and convention facilities.

It originally opened in 1994 and later rebranded as Caesars Windsor. If you do think you’ll head there, take a look at who might be doing a show, as they bring in popular bands and artists on the regular.

I’d highly recommend booking a stay at Caesars Windsor if you’re looking for a memorable and momentous stay while you’re in town.

Make Time For Ford City

Ford City isn’t always on a visitor’s itinerary when they’re coming to Windsor, but it should be. In fact, I feel so strongly about that, we’ve got a whole article just about Ford City over on my sister site, Ultimate Ontario.

It’s a historic neighbourhood closely tied to the automotive industry (hence the name). Not shockingly, it was established by the Ford Motor Company in 1904, and it became an industrial and residential hub. Over the years, it faced economic challenges (largely due to the decline in the automotive industry) but has seen recent revitalization efforts, preserving its historic character.

Nowadays, you can see murals everywhere showcasing the roots of the neighbourhood, but there’s also very much a sense that it’s brightest days may be ahead of it. It’s worth the time to walk up and down the main drag, popping into a variety of shops, and stopping somewhere for a bite to eat. Sawyer’s Craft BBQ would be my choice in the neighbourhood if you’re hungry!

Have Some Fun at Adventure Bay Family Water Park

This is one of the top things to do in Windsor if you’ve got a family in particular, but I went on my own here, and was lucky enough to have Michael Chantler, who runs the show here, give me a run of the place.

It’s located in the heart of the city, yet at 35,000 square feet, it certainly doesn’t lack in size for a downtown water park. There are water slides, kids play areas, lazy rivers, wave pools, and perhaps my personal favourite, the FlowRider.

The FlowRider is an innovative surf attraction that creates artificial waves using jet-propelled water, providing a really unique surfing experience that, in Canada, is hard to find. I started off on my stomach, facing the waves head on and having a blast, but experts can stand up on this bad boy and really showcase their skills.

One thing to note, typically Adventure Bay operates 12-4pm, and that’s largely because they offer private classes outside of those hours for ambitious flow riders, Aquafit classes, River Walking, and kids programming like “Wave Babies.”

Take Flight at the Canadian Aviation Museum

Mid “Flight Experience” at the Canadian Aviation Museum

If you’re at all interested in Canadian aviation or military history, this museum has a lot to catch your eye, and a dedicated, knowledgable staff.

My grandfather was a WWII pilot, so this place spoke to me - so much so that I wrote a full article on the Canadian Aviation Museum over on another of my sites, We Explore Canada. You can peruse the impressive collection of aircrafts, take a tour to really dive into the nitty gritty, or even book a flight experience, which is something that I did, and I will honestly never forget it for the rest of my life.

I got to fly in the Harvard, a plane that my grandfather would likely have trained on before heading off to a Royal Canadian Air Force base in the UK.

In the spring and summer, they tend to operate Tuesday through Saturday 10am-4pm, and in the fall and winter, they’re open Thursday through Saturday, 10am-4pm.

Visit WIndsor’s Parks and Gardens

Windsor has done a nice job of setting up outdoors space for its citizens and visitors, and you might as well take advantage of that on your own visit to the city, especially if you happen to have little ones in tow. Here are some spots that you might want to have on your radar:

Dieppe Gardens: Located along the Windsor waterfront, Dieppe Gardens offers some picturesque views of the Detroit River and the Detroit skyline (so don’t forget to bring a camera). It features beautifully landscaped gardens, walking paths, and a Peace Beacon monument in honour of fallen Canadian soldiers.
Coventry Gardens: Situated next to Dieppe Gardens, Coventry Gardens is known for its impressive Peace Fountain, which is actually illuminated at night. The park also has sculptures, walking paths, and a riverfront promenade.
Jackson Park: This historic park in downtown Windsor boasts a lovely little landscape with mature trees, flowerbeds, and walking paths. It's a tranquil spot for a planned picnic, or perhaps just a leisurely stroll.
Malden Park: One of the largest parks in Windsor, Malden Park offers a wide range of amenities, including sports fields, walking trails, and a pond.
Lakewood Park: Okay, so this is technically in Tecumseh, but it’s only a 15 or so minute drive from the downtown core, and the reason I mention this is for the disc golf lovers. I ended up playing the Lakewood Park Disc Course, an 18 hole public course, and it was a blast.
Sandpoint Beach Park: Located on the shores of Lake St. Clair, Sandpoint Beach Park provides a sandy shoreline for swimming and sunbathing during the summer months. It’s also a nice place to simply take a walk.

Explore Walkerville - My Favourite Neighbourhood in Windsor

Learning about Walkerville’s boozy past during the J.P. Wiser Experience

It is not an accident that my article on Windsor’s Walkerville neighbourhood is the top article on the neighbourhood - and that’s because I adore it, and I’ve explored it extensively.

Walkerville is renowned for its well-preserved historic architecture, particularly the houses built by Hiram Walker and the Hiram Walker and Sons Distillery. You should find time to peruse the elegant homes, but do note that that you’ll also want to visit the distillery and dive into this history a bit.

It’s extraordinary, as it was essentially a model town headed up by Hiram Walker (hence “Walkerville”). If you want to do a full tour of the area, then you should certainly do the J.P Wiser Experience to start so you actually understand what makes Walkerville, Walkerville.

After that, I’d plan to do pizza and pints at Walkerville Brewery, then peruse the shops and cafes on the main strip. I typically also pop into Anchor Coffee House for one a cup of java and one of their “Egg-scone wiches.”

There are also art galleries, and Willistead Manor, which I’ve written about in more detail below.

Go Out For a Bite

There are a lot of good restaurants to go out to in Windsor. Here are some of my favourites:

Nico Taverna: This Mediterranean restaurant in the heart of Windsor serves fresh and flavorful dishes with a focus on seafood, pasta, and traditional Greek cuisine. The waterfront view adds to the dining experience.
Sawyer’s Craft BBQ: This spot in Ford City has all your favourite BBQ classics, but they’ve really put their own spin on it. If weather allows, I’d strongly recommend getting a spot in the back (not far from their epic smoker), and soaking in the vibe. The mural in the back area certainly doesn’t hurt that aforementioned vibe.
The Twisted Apron: Known for its farm-to-table concept, The Twisted Apron focuses on fresh, seasonal ingredients to create a diverse menu of contemporary dishes with international influences. I personally think they do brunch particularly well, so perhaps time your visit to be able to take advantage of that.
Terra Cotta Pizzeria: If you're craving pizza, Terra Cotta is a local favourite. They serve wood-fired, Neapolitan-style pizzas with a variety of toppings and other Italian dishes.
Funky Chow Kitchen: This relatively new spot in Walkerville has became a staple for locals and visitors looking to get their hands on a delicious bao bun, noodle dish, or sushi. Sometimes Asian fusion can be a touch too ambitious, but they pull it all off rather nicely.
Armando's Pizza: Forget “Detroit style pizza” for a moment, and embrace Armando’s “Windsor style pizza.” They’ve got a few locations, and they’re all passionate about serving up what has become some of the most famous za’ in the region.
Spago Ristorante Italiano: Offering classic Italian cuisine in an elegant setting, Spago is known for its pasta dishes, seafood, and a fine selection of wines. It's an excellent choice for if you’re looking to take someone out on a date!
Mazaar Lebanese Cuisine: Mazaar offers a taste of Lebanese cuisine with a menu featuring a variety of kebabs, shawarma, and traditional Middle Eastern dishes. The restaurant is known for its welcoming atmosphere and generous portions.
Mamo Burger Bar: Known for its gourmet burgers and creative toppings, Mamo Burger Bar offers a selection of handcrafted burgers made with locally sourced ingredients.

Other local favourites include Eddy’s Mediterranean Bistro, Souq Lebanese Grill, Mezzo Ristorante & Lounge, The Cook’s Shop, and there’s also The Keg.

Stay Somewhere Interesting

On my most recent visit to Windsor, I had the pleasure of staying at The DoubleTree by Hilton Windsor Hotel & Suites, which is a perfectly located downtown hotel in the heart of the action. It offers comfortable rooms and suites, a dining restaurant, meeting facilities, fitness amenities, and, of course, a warm welcome with their signature chocolate chip cookies.

It’s literally steps away from the trails that roll along the waterfront, and thus the Windsor Sculpture Park. Walking down to catch my Windsor Premier Cruise was also a breeze - I think it took me about 90 seconds!

I’d also be remiss not to mention my dining experience at The River Room, where I was able to meet Chef Stan Spanos who is working hard to create a premiere dining experience in Windsor. It skews towards upscale, creative mediterranean cuisine, and I thought they did a brilliant job.

My brother and I also stayed at the Caesars Windsor, and when you come in from exploring Windsor, Caesars makes sure that the fun keeps on rolling on. Dave and I had a blast here, and loved the energy of the whole complex, especially because they were open late!

Tour Willistead Manor

A 36-room historic mansion within a 15-acre park - what’s not to love?

Willistead Manor was constructed between 1904 and 1906 for Edward Chandler Walker, a prominent Canadian businessman who was the son of Hiram Walker, the founder of Hiram Walker & Sons Limited, a major distillery in Windsor. The mansion was designed by renowned architect Albert Kahn in the Beaux-Arts architectural style.

The mansion is considered one of the finest examples of Beaux-Arts architecture in Canada, and calls Walkerville home, a neighourhood that you’ll notice is on this list of its own accord because of all it has going on.

Willistead Manor has had various uses throughout its history. After the Walker family, it served as a veterans' hospital, a public school, and even a city hall. Today, it is primarily used for cultural and community events.

When you visit, it makes sense to do a tour (which you can find more information about here), but I’d also allot some time to explore the beautiful surrounding gardens.

Set Eyes on The Windsor Sculpture Park

They describe the Windsor Sculpture Park as “a museum without walls” and I quite like that summary. In short, it’s a park that straddles the river, showcasing about 35 large-scale works from top-tier artists.

The Windsor Sculpture Park is primarily situated along the Detroit River between the Ambassador Bridge and The Art Gallery of Windsor, encompassing Ambassador and Centennial Parks, respectively. Additionally, some sculptures are found in other Windsor parks, including Reaume Park, Jackson Park, Vision Corridor, and City Hall Square.

Personally, I woke up early one morning and rented a Bird Scooter to see if I could see as many as possible. The City of Windsor has a list of all the sculptures and where you can find them right here. Don’t be too stressed though, you’ll happen across many of them simply by walking (or scootering) along the Detroit River, then visiting some of the major parks in the city along with City Hall Square.

Indulge in a Little Wine

Bri and I adore the emerging (and wondrous) wine country so much here in Windsor Essex Pelee Island, that we’ve got an entire article dedicated to it over on Ultimate Ontario. That’s a great resource to plan a strategic route around this wine country on your way to or from Windsor - or using Windsor as your base.

It’s located in and around Harrow, Ontario, and you could easily spend a few days just on this trail. You could be sipping at Colio and Cooper’s Hawk, then find yourself at lunch at Oxley in the sunshine, followed by North 42 and pizza at Paglione, and even spend a day or night over on Pelee Island, while making time for Pelee Island Winery.

We’re fans of the EPIC Wine Tasting Pass, personally, and there is no right or wrong way to do it. The only that things feels wrong is that more people don’t know just how epic the EPIC Wine Country is!

Bring Along Your Bike!

If you’re a longtime reader, it won’t surprise you in the slightest that I’m recommending a little cycling here. Cycling in Windsor Essex Pelee Island is an absolute treat as well, and you’re in luck, because I’ve written one of the most comprehensive cycling guides to Windsor Essex Pelee Island around.

Generally speaking, you’ll want to spend some time cycling on the Windsor Riverfront Trail, the Wine Trail, the Parkway Trail, the Pelee Trails, or the Lakeside Trails. In short, you’ve got options, all of which I carefully go over in the linked post above.

Hop Aboard a Windsor Premier Cruise

Aboard my 2 Hour Sightseeing Cruise of the Detroit River

Windsor Premier Cruises typically offers a range of cruise experiences along the Detroit River. These include sightseeing cruises, dinner cruises, special events, private charters for various occasions, and corporate functions.

My vote would be for the 2 Hour Sightseeing Cruise of the Detroit River. It offers views of the “historic Detroit River, including Hiram Walker, Belle Isle, waterfront mansions, and other notable locations.” I liked that it took you up close and personal with the Detroit skyline as well.

Windsor and Detroit are cities that should be viewed from the water to get a real perspective and the context you need to fully understand and explore these destinations. You can see details on all the tours they offer (everything from fireworks cruises to Halloween spooky cruises) here.

Stroll Through the Ojibway Nature Centre

The Ojibway Prairie Complex, situated in the southwest corner of Windsor, boasts a recorded count of 247 distinct species, which makes it a favourite spot for nature lovers.

It stands as a premier location for immersing yourself in wildlife and natural surroundings. Here, you'll find an extensive network of over 15 kilometres of hiking trails winding through woodlands and prairies.

Moreover, you’ll find a that there’s a centre on the complex staffed with knowledgeable naturalists. Inside, you'll encounter wildlife exhibits, hands-on programs, and more.

Grab a Pint At One of Windsor’s Breweries

If there’s one thing that I excel at, it’s grabbing a flight and enjoying the vibe at a local brewery (and I’ve actually written a full article as well about Windsor’s brewery scene). Here are some of my favourites in the Windsor area:

Sandwich Brewing Company: Located in Windsor's historic “Sandwich Towne”, this brewery offers a variety of craft beers, including IPAs, stouts, and seasonal offerings. The brewery has a welcoming atmosphere with a focus on community engagement. I loved their “White Bronco” as well as “Prarie Sunshine.”
Frank Brewing Company: This isn’t in the central core, but it’s worth making a detour for. If it’s a hot day, you’ll want to sip on their “Sombrero Cerveza” or “Sunshine,” but start with their “Straight Up Lager” so that you can taste the brewing process.
Walkerville Brewery: I mentioned this up above, but there’s simply no reason to not pop in here when you’re exploring the Walkerville neighbourhood. I like their “Electric Haze Juicy IPA” a lot, and am also a big fan of their “Purity Pilsner.”
Chapter Two Brewing Company: Located in a historic building, Chapter Two offers a cozy setting to enjoy their craft beers. They have a selection of traditional and innovative beer styles, and you can often find food trucks on-site.
Craft Heads Brewing Company: Craft Heads was just a short walk from where I was staying most recently, so this was absolutely going to make the list. They have a really impressive range of beers here that range include light/blonde ales, pale ales and IPAs, seltzers, sours, dark beers, and adventurous brews. This is a good spot to pad your Untappd profile if that’s your type of thing.

Pro tip - if breweries are your thing (and epic sandwiches), then make a stop at Cured Craft Brewing Co. on your way to or from Windsor.

Pop By Maiden Lane Wine & Spirits

Use this as an excuse to explore Maiden Lane, and some of the epic street art around here. They’re a bar and bottle-shop in downtown Windsor that just does things a little differently.

Founded in June 2019 by Mark Dutka, a third-generation bartender, and Sarah Dewar, a 20-year wine industry veteran, it offers a diverse selection of expertly mixed cocktails, unique wines, craft beers, and ciders. The atmosphere is complemented by quality food, great music, and a relaxed vibe, making it a welcoming spot for all.

I had the chance to chat with Sarah, and I just can’t say enough about how hard they work to create an exceptional experience for locals and visitors. I ended up sipping on a “Pigs Can Fly,” which featured Dewar’s blended scotch, lemon, honey syrup, dolin rouge, campari, and dehydrated strawberries - all on the rocks.

Let me tell you - the cocktails here are off the charts. Their food menu is as innovative as their drink menu, so certainly don’t hesitate to save some room and create a custom charcuterie board when you get here.

Windsor Awaits

As I hope it now evident, there’s a lot to do here, and that also means there’s something for everyone. The fun part, for me, is that I know I can continue to come back here again and again, because it’s also an ambitious city that always has more in the works.

However you approach it, I hope this guides you to creating some wonderful memories in a very underrated Ontario city.

I want to thank Tourism Windsor Essex Pelee Island for hosting me as media. That said, all opinions are completely my own. If you appreciated this article, you’ll love our newsletter, as well as our Facebook group! Feel free to join, all are welcome.