3 Days in Windsor, Ontario: A Long Weekend Guide to Neighbourhoods, Outdoor Adventures & Events
Windsor is a dynamic city of neighbourhoods, each with their own distinct history and community spirit. Chris and I recently spent a long weekend in the city, and with such a variety of things to do it was easy to create this guide to help you spend 3 days on your next trip to Windsor!
Chris and I taking in the views from Malden Park’s trails
Chris has spent plenty of time in Windsor, but up until our recent three day getaway, I’d spent a lot of time in the Windsor Essex region in nearby places like Kingsville, Amherstburg and Pelee Island. But I’d only been in Windsor’s city proper for a handful of hours at most, including visiting friends who attended the University of Windsor when I was in my university days.
It was long overdue for me to properly check out the city, and I left with so much appreciation for all of the things there are to do in Windsor.
Windsor can be a bit of a daunting city to approach for a visit over a weekend or long weekend. While there are many sections of the city that are walkable and concentrated near its downtown core, visitors should think of Windsor as a city of neighbourhoods, instead of just one city with one singular downtown core. It’s a lot like my hometown of Toronto, in that way—another city where its neighbourhoods are what make it special.
I’ve put together a 3-day itinerary that I think really demonstrates the diversity of Windsor. From appreciating history, arts and culture to enjoying seasonal festivals and events and its ever-growing restaurant scene, there’s plenty to occupy your time with. Add in a few places to go walking or cycling both in and around the city and a few top-notch craft breweries, and you’ve got yourself one heck of a long weekend destination, in my opinion!
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Why Take a Long Weekend in Windsor?
Like any city of neighbourhoods, spending a long weekend here helps you familiarize and appreciate all that’s going on in each distinct area. It also gives you the time to slow down and appreciate some of Windsor’s outdoor spaces, nature trails, and chances are you’ll catch a show or some sort of performance while you’re in town. You’ll find that there’s even an option to go canoeing on a nearby river here in this 3-day itinerary!
The itinerary below is organized into three full days, so depending on when you’re arriving and departing the city, you may want to shuffle a few things around. I’ve tried to make the itinerary as logical as possible based on activities to do, places to visit and locations of neighbourhoods.
Where to Stay in Windsor
There are many different accommodation options in and around Windsor, but staying downtown in a river view room at either the DoubleTree by Hilton Windsor or the Best Western Plus Waterfront Hotel is a highlight. The views of the Detroit Skyline and the Detroit River are beautiful from downtown Windsor, and the views change with the weather from morning to night.
Of course, you’re welcome to take a look at places to stay in Windsor using this map to find the right fit for you.
Special Events and Seasonal Activities
Windsor is a great destination any time of year, but as with any city there are different things going on in each season. You’ll find that Windsor’s outdoor spaces come to life from spring to fall, and there are other events going on at various venues throughout the city. Here are a few events to be mindful of ahead of your trip:
The Downtown Windsor Farmer’s Market: This weekly outdoor market has one of the longest runs of Canadian markets that I’m aware of—the season starts at the end of March and runs until the end of October. It’s a great community market with all sorts of produce, craft, clothing and food vendors. You can find the market on Pelissier Street between Park St. W and Wyandotte St. E on Saturdays.
The Windsor International Film Festival: WIFF is an 11-day festival that runs around late October to early November each year. It’s a non-profit film festival which shows the most films and has the largest amount of francophone films out of all film festivals in Canada. There are many events and screenings taking place throughout the city during WIFF, and I’d even encourage you to plan a trip specifically while the festival is running.
Performances in Town: With organizations and venues like the Windsor Symphony Orchestra, the Capitol Theatre Windsor, the Chrysler Theatre, Caesar’s Windsor and more, there are all sorts of shows and performances happening in Windsor throughout the year. Do a little research before your trip to see if there’s anything on while you’re in town.
WIFF Alley
Visiting during the Windsor International Film Festival makes for a fun way to experience the city! Plenty of events and installations take place downtown.
3 Days in Windsor Itinerary, Day 1: Downtown & the Riverfront
Breakfast at The River Room
If you’re staying at the Best Western Plus Waterfront Hotel, enjoying breakfast or brunch at The River Room is an especially great way to start the day.
This newly renovated space is warm and welcoming, with floor to ceiling windows looking across the Detroit River to the Detroit skyline. There’s nothing quite like the way the morning sun hits the city’s Art Deco skyscrapers. I could admire Art Deco architecture all day!
You can opt for a buffet breakfast here, but I’d recommend ordering from their a-la-carte menu. They have everything from staples like Eggs Benedict to Shakshuka. And honestly, even their Yogurt Parfait was a really nice way to start the day.
Walk the Riverfront Trail for its Views, Art & History
I’ve been on quite a few urban trails across Canada and around the world, and I can confidently say that Windsor’s Riverfront Trail is a delight to walk or bike along.
The Riverfront Trail is a dedicated pedestrian and cycling trail. It’s approximately 5km long, and part of the Trans Canada Trail network. As you walk the trail from downtown Windsor towards the Ambassador Bridge, you can admire the views of the river across to Detroit, visit the Windsor Sculpture Park (home to over 30 large-scale sculptures), and check out Streetcar No. 351.
Streetcar No. 351 is inside of the Legacy Beacon at 780 Riverside Drive West. It’s a restored 1918 streetcar trolley commemorating Windsor’s public transit history as the first city in Canada to introduce an electric streetcar system in 1886. Although the city’s streetcars stopped operating in the 1930s, seeing this car today is a nice way to learn about and honour its past.
Note: The Legacy Beacon building is open seasonally, usually from May 1 to October 31.
Sculpture Park
“The Spaghett” small batch lager
Head to Sandwich Town for Lunch and a Craft Pint
After walking the length of the Riverfront Trail from downtown to the Ambassador Bridge, it’s only a little further to walk to Windsor’s Sandwich Town neighbourhood. I’m a big fan of walking to get acquainted with a city, and this is a great way to spend some time on foot in Windsor.
Originally established as the village of Sandwich in 1797, it is one of the province's oldest and most historic settlements. Today, Sandwich’s main street has a number of shops and restaurants, and runs several blocks from around Detroit Street to South Street on Sandwich Street.
The aptly named Sandwich Brewing Company is a great place to come for a delicious pint of local craft beer and a bite for lunch. On the beer side, they’re known for reliable staples and creative, small-batch releases on tap. Their list changes regularly, so there’s usually something new to try alongside their core beers.
Chris and I enjoyed a slow afternoon sipping on a few craft brews here. I’d highly recommend ordering a sample flight of four so you get a good taste for the delicious beers they make in-house. They also have a small but mighty selection of cheese and charcuterie nibbles and sandwiches for lunch.
Plan to spend a little time walking around Sandwich Town afterwards for shopping, window peeping and appreciating all this neighbourhood has to offer.
Visit Museum Windsor & Art Windsor Essex
Back in downtown Windsor, Museum Windsor and Art Windsor Essex are in one building on Riverside Drive. This was an especially fun place to visit for me, since my grandpa was born in Windsor and there were several artifacts from around the time he and my great-grandparents would have lived here.
The museum offers an overview of Windsor’s local history, while the gallery showcases a rotating selection of exhibitions that highlight artists from the region and beyond. Chris and I spent time wandering through the displays before popping into the small gift shop at Art Windsor-Essex, which carries locally made products and independent artwork.
Whether you need a little time to freshen up at the hotel or you’re looking for another food stop, The Loose Goose is a good place to go for a casual dinner downtown. They have plenty of beers on tap, and over 50 types of wing flavours to try!
Taking in the galleries at Art Windsor Essex
Caesars Windsor
Try Your Luck or Catch a Show at Caesars Windsor
Yes, that Caesars! The famous Caesars Palace of Las Vegas has a location here in Windsor. They have several gaming rooms, restaurants, bars and different performances that come through town.
There were no shows during our visit, so Chris and I hit the casino for a bit of gaming (we typically only agree to spend around $20 each for a little fun—it’s important to always play responsibly), and we had a few cocktails at Legends Sports Bar and Cosmos Lounge on site.
Day 2: Nature Trails, Historic Walkerville & Ford City
Walk the Trails at Malden Park
On your second day in Windsor, start the day with some fresh air at Malden Park. This park is a short drive from downtown Windsor, with several walking trails, a small lake and off-road mountain biking paths.
Head all the way up to the top of the hill in the park to the observation area for views of the modern Gordie Howe International Bridge. If you’re looking for an extra walk or bike, once this bridge is open, pedestrians and cyclists can use it for free.
Gordie Howe International Bridge views from Malden Park
Willistead Manor tour in Walkerville
Shopping, History and Dining in Walkerville
Another neighbourhood that used to be its own “city” within Windsor is Walkerville. It was originally founded by Hiram Walker—the owner of Canadian Club whisky—in 1890. Its main street runs along Wyandotte Street East, between Walker Road to around Gladstone Avenue.
My great-grandparents actually moved to Walkerville when they first immigrated to Canada in the early 1900s, and my grandpa was born here, so it was really nice for me to have the chance to finally check it out.
A good place to start your time in Walkerville is with a visit to Willistead Manor. This estate home was built by Edward Chandler Walker, the son of Hiram Walker. With its striking oak doors, elegant rooms, and surrounding gardens, the manor is a great place to come for a tour, if you arrange it ahead of time. If you’re unable to take a tour, appreciating the estate from outside and walking around its grounds that are now a public park is another option.
There’s plenty of great shopping and dining along Wyandotte Street East in the heart of Walkerville, too. Urban Art Market is a favourite shop with all sorts of different clothing, accessories, pottery and other pieces produced by local Windsor vendors. And once you’re done shopping and window peeping, there is a brewery and several other restaurants in the heart of Walkerville.
Make sure you check out our full guide to Walkerville for all the details on how to spend your time here!
Take a Ford City Neighbourhood Walk & Pottery Class
Street art in Ford City
Co-owner of Ford City Potters, Gisele Bick, giving a class demonstration on the wheel
Ford City is more or less around the corner from Walkerville. By now, you’ve realized that Windsor is really made up many different “cities” and towns established by wealthy industrialists at the turn of the century, and the namesake for Ford City should come as no surprise to you.
Ford City was incorporated as a village in 1913, and became a town in 1915. It was established as a company town after the construction of the Ford Motor Company of Canada’s Plant 1 in 1912.
Today, it’s an evolving historic area of Windsor, and it’s worth walking around the neighbourhood along Drouillard Road between Edna Street and Richmond Street to check out its shops, cafes, restaurants and vibrant street art. There’s so much to do in this neighbourhood that Chris wrote a full guide to it. If you’re planning to spend a while here, it’s definitely worth the read.
It’s also the perfect place to get creative during your visit, by taking a class at Ford City Potters. This welcoming, woman-owned studio is a community-forward endeavour offering pottery classes to students of all skill levels. They have classes for novices and potters of all levels, which you can learn about on their website.
Bear in mind that pottery often takes some time to fire up and finish. You can communicate with owners Gisele and Lisa ahead of time to figure out the best way to plan your visit and pick up and/or ship your pieces after your class.
Have Dinner at Erie Street Gastropub
Ice cream flight at Erie Street Gastropub
Views of the Detroit skyline from our stay at the Best Western Plus Waterfront room
Erie Street Gastropub is a popular spot known for its Vietnamese-fusion menu. The restaurant pairs creative dishes with an on-site craft beer selection, making it an easy choice for a relaxed evening meal.
You need to make sure you save room for dessert here. A highlight at Erie Street is their house-made, small-batch ice cream. You can select one flavour or try an ice cream flight with four flavours, which is of course what Chris and I did. Some of their ice cream flavours are even infused with spirits, like the Oreo Mudslide with vodka, Kahlua, Baileys and Oreos. This was the perfect way to cap off another great day in Windsor.
Like with any evening in Windsor, it’s always a good idea to look into night time theatre or music performances and other events in the city. You can check out this resource for some ideas.
Day 3: Downtown Highlights & Outdoor Adventures
There are so many breakfast and brunch spots in downtown Windsor, but for today’s itinerary I’d recommend grabbing a quick breakfast or something to-go.
Chris and I happened upon Cafe March 21 when we were walking along the Windsor Farmer’s Market one morning, and it’s a cozy little Korean cafe with all sorts of pastries, snacks, breakfast and lunch options. They serve great coffee, too!
Go Canoeing on the Canard River
Chris and I try to get out on the water if we can when we travel, and there are some awesome paddling opportunities along the Canard River just outside Windsor.
This peaceful waterway is a system of rivers winding through wetlands and natural areas inland from the Detroit River, making it a great spot for wildlife viewing. If you have a passion for birdwatching, this is an especially great place to see a variety of the region’s bird species.
You can either take a guided tour or rent canoes from the River Canard Canoe Company, which operates from early spring to late fall. They’re located in the hamlet of River Canard at Malden Road and the River Canard Bridge, and you can find more details on their website.
Chris enjoying a late fall paddle on the Canard River
Trying the Windsor-style pizza at Antonino’s is a must
Indulge in Windsor-Style Pizza for Lunch
Windsor-style pizza came to be thanks to many Italian immigrants who settled in Windsor and opened pie shops beginning in the late 1950s. Windsor’s pizza is known for its medium-thick to thick cornmeal and flour-based crust and rich cheeses. Many true Windsor-style pizzas are also served with shredded pepperoni and/or canned mushrooms.
There are several different places to try Windsor-style pizza in the city, but Antonino's Original Pizza is one of the long-time favourites in town. This family-run spot has been serving pizza in Windsor since 1959, and has become something of a local institution over the decades.
Chris and I tried a half and half pizza of two of their best known pies—The Angry Hawaiian and The Deluxe. These were so good, and if you have room for dessert, their cannolis are delicious.
Spend an Evening on Maiden Lane
Maiden Lane Wine & Cocktail Bar on Maiden Lane
The Bamboo + The Monte Carlo
Maiden Lane is a pedestrian laneway between Ouellette Avenue and Pelissier Street in downtown Windsor. It’s home to part of the Windsor Art Alley and the special spot that is Maiden Lane Wine & Cocktail Bar.
Wrapping up a trip to Windsor with at the very least a cocktail here is a must. But don’t be fooled by their name—while the bar originally built its reputation on expertly crafted drinks, a thorough wine list and a comparable beer list, it has since expanded to include a chef-driven menu of small plates and dinner options.
Spending time in this cocktail bar will be the cherry on top of a memorable trip to Windsor. The cocktail list is thoughtfully curated, and the staff are incredibly knowledgeable and happy to suggest something based on what you typically enjoy. When Chris and I visited, we enjoyed The Bamboo and The Monte Carlo.
Three Days Well Spent in Windsor
And there you have it, a cool three days in Windsor filled with a healthy mix of outdoor activities, an understanding of the city and its neighbourhoods, plenty of ways to appreciate creativity, arts and culture, and have fun while enjoying delicious food and drinks at several of its restaurants, breweries and events.
I hope you found as much joy reading this article as I found writing it. Windsor is a great city that deserves to be celebrated, so much of which is rooted in its passionate community members and local businesses.
I’d like to thank Tourism Windsor Essex Pelee Island for hosting Chris and I as media on this trip to Windsor. All opinions expressed in this article are completely my own.
Bri Mitchell
Bri Mitchell is a travel writer and content creator from Toronto, Ontario. She loves to highlight all things nature, food, wellness, sustainability and adventure in her work. Bri writes and shares her travel experiences from across Canada, the United States and around the world on Instagram and TikTok (@brimitchelltravels); in her articles for travelingmitch, Ultimate Ontario, and We Explore Canada; and in her weekly travel newsletter, The Weekly Traveller.