There may be more famous Windsors in the world, but this one is Canada’s Windsor. Whist there is not a castle or Royal in site, this border town is pretty good fun with a fun Downtown area, a student population and plenty of natural and historic sights nearby.
You’re going to find a surprising amount of things to do in Windsor, Canada ranging from old manor houses, big bridges to whiskey tours. If you want to get a little more under the skin of this interesting city, you’ll need a little insider know-how – a little help seeing what’s what.
Therefore we have also listed the most unusual things to do in Windsor, Canada. We’re providing you with a guide to the coolest and most under the radar attractions and destinations you can find here, from a strange planned 100 year old community for employees of a whisky distillery, all the way to soaking up the ornate buildings of the university here. We’ve got your trip to Windsor totally sorted.
Table of Contents
- Top Things to Do in Windsor, Canada
- Unusual Things to Do in Windsor, Canada
- Things to Do in Windsor, Canada at Night
- Where to Stay in Windsor, Canada
- Romantic Things to Do in Windsor, Canada
- Best Free Things to Do in Windsor, Canada
- Windsor Packing List
- Best Things to Do in Windsor, Canada with Kids
- Day Trips from Windsor, Canada
- 3 Day Windsor, Canada Itinerary
Top Things to Do in Windsor, Canada
As ever let’s start at the start. The top things to do in Windsor are the sites and experiences that every Detroit day-tripper has to be do, the things you cannot miss when you’re in Windsor, Canada.
Whenever you are in Canada, you absolutely must give Poutine a try.
This iconic snack is french fries topped with cheese curds and drizzled (or slathered) with gravy. That’s right. These tasty morsels are one of Canada’s best-loved foodstuffs and very satisfying after a night of drinking. Finding the tastiest poutine going is most definitely one of the top things to do in Windsor, Canada.
2. Spot the Ambassador Bridge from the Riverfront Trail
Built way back in 1929, the 90 year old Ambassador Bridge in impressive structure linking the US and Canada over the Detroit River. Of course, borders being borders, it’s not exactly straightforward to cross back and forth over the bridge.
That’s right, the bridge connects the two countries but you don’t have to cross it to see it in all of its glory. For one of the best things to do in Windsor, Canada, take a stroll along the Riverfront Trail and soak up the sights and the sounds from alongside the water’s edge. There’s some pretty cool sculptures dotted alongside the river for you to spot along the way, too (but more on that later).
- Go and marvel at the decommissioned steam locomotive, Spirit of Windsor
- Make sure you go to EDDE’s Graffiti Alley
- Grab something to eat, specifically a tasty burger, from Bubi’s Awesome Eats
You might not have guessed this, but one of the most quintessential things to do in Windsor, Canada is to try out some of its whisky. It turns out this town is pretty famous for its whisky and there are a whole bunch of different distilleries where you can try some of the good stuff for yourself.
For a start there’s Hiram Walker & Sons Limited Distillery, the largest distillery in North America. There’s the Windsor Club, the Canadian Club Brand Centre, and then there’s Walkerville Brewery. Take a Distillery Tour and see for yourself why Windsor is also known as Whiskytown!
4. Hang out in Jackson Park
Located just south of Downtown Windsor, the well established Jackson Park has more than 10,000 plants to its name – many of which are situated in its charming sunken garden. Exploring this green space is easily one of the better outdoorsy things to do in Windsor, Canada.
You’ll find more than just greenery here though. The whole space of Jackson Park is strewn with monuments from war memorials to fountains, all criss crossed by comprehensive pathways that allow you to easily explore what’s going on. There’s good seasonal events to discover here, too, like winter light-ups and is naturally a good place to chill out in the summer and hide from the heat.
Canada isn’t particularly well known for its wine (it’s more about the whisky here). However, there are actually a fair few wineries in the area of Windsor, Canada which you can seek out and spend the day sampling some of the good stuff.
One of the nearby wineries in question, located in Harrow, offers up tastings and paired snacks to go with the choice of wines. That’s Coopers Hawk Vineyards, just so you know. Elsewhere, Pelee Island has its very own winery. Either way, if you’re a fan of wine, this is will definitely be a top thing to do in Windsor, Canada.
6. Check out the grand Willistead Manor
Dating back to 1906, the very grand mansion that is Willistead Manor is very impressive indeed with its Tudor-Jacobean revival style of architecture.
Visiting to see what all the fuss is about is definitely one the best things to do in Windsor, Canada – but make sure you visit on the right day. It’s open to the public from July to December, but only on certain days (Wednesdays and Sundays); there’s also the 15 acre grounds to stroll around if that’s what you feel like doing.
Unusual Things to Do in Windsor, Canada
Whilst there isn’t exactly a tourist trail in Windsor, there are plenty of day-trippers from the States hopping over for a look. Therefore, if you want to find the unusual things to do in Windsor, Canada, read on..
Though you’ll find Lake St Clair to the north of the city, in the south is the more famous and much huger Lake Erie. It’s possible to visit on a day trip from Windsor, Canada – and one of the best ways to do so and explore the shoreline of Lake Erie is to head off on a bicycle. There are a number of bike places to rent your own wheels in town, including Cyclery Inc. and Ambassador Bicycles.
Once you’ve scored your own bike, it’s time to pedal out into nature for one of the best outdoorsy things to do in Windsor, Canada. Soak up the beauty of the lake, do a spot of birdwatching, hit up some beaches, and make life as easy (or as hard) for yourself as you feel like via a number of trails of varying length.
8. Have an adventure on Pelee Island
One of the best day trips from Windsor, Canada that you could ever embark on is making the voyage to Pelee Island. Located in the western portion of Lake Erie, there’s a ferry service which makes getting out over to this little islet pretty simple; all in all, it takes around 2 hours to travel from the city centre to Pelee Island.
Claimed to be one of Canada’s best-kept secrets, this island actually constitutes the most southerly inhabited part of Canada. Once you’re on the island you’ll have a whole load of things to do. You could spend some time discovering its impossibly charming churches, hike its beautiful trails, or simply make a beeline for a beach and go for a swim. Or you could simply shop at the artsy boutiques.
9. Stroll through the University
Surprisingly, one of the best things to do in Windsor, Canada is to spend some time exploring the pretty, historic buildings of the University of Windsor itself. And there’s a lot of history here; Dillon Hall, one such very grand and very ornate building, dates back to 1857 and definitely warrants a photograph or two.
Spread around 130 acres, the campus is home to a whole load of buildings and examples of Christian architecture mixed in with modern buildings. There’s even an arboretum here that you could spend some time wandering around. Not something that’s on the usual tourist trail, exploring the University is one of those more off the beaten track things to do in Windsor, Canada.
Safety in Windsor, Canada
Windsor, Canada isn’t an unsafe city. Some will tell you it’s rough around the edges, which isn’t untrue, but it’s generally safe: a popular tourist destination for Americans, and a university town to boot, in a country with statistically less crime than its southern neighbour.
It’s a border town with something of a reputation for dodgy dealings (i.e. drugs), but overall it’s a safe, quiet place to spend time. Like in any city though, there are places you might not want to hang out late at night by yourself – but that’s like anywhere.
Fridays and Saturday nights can get quite rowdy with many students and revellers coming over the border to party in Windsor’s nightclubs (Canada’s legal drinking age is 19, compared with the States’ 21). You get the picture.
When it comes to weather, you might want to think about bringing warm clothes and plenty of layers if you’re visiting in winter. Don’t even think about going swimming anywhere at that time of year: it will be freezing!
All in all, there isn’t too much to worry about when considering how safe Windsor, Canada is. If you want to be extra careful, consider a money belt (such as the Active Roots Security Belt), but other than that, we think you’ll be ok. Read our tips for traveling safely before you fly and always get travel insurance. Check out our roundup of the best travel insurance.
Things to Do in Windsor, Canada at Night
From student bars to theatre performances, there is more than enough to do in Windsor at night to keep you going past midnight.
10. Catch a show at the Chrysler Theatre
Maybe you’re a keen fan of drama, comedy or musicals ? Or perhaps you’re just looking for entertaining things to do in Windsor, Canada at night? Well in case you don’t feel like simply exploring the sometimes quite rowdy and raucous bar scene, head on over to the very charming Chrysler Theatre.
Located in Downtown Windsor, the Chrysler Theatre is an intimate, 200-seat affair. It’s perfect for seeing smaller artistic productions, but specifically, this well loved theatre with its grand interiors is a centre for the arts of St Clair College. Check online and see what’s going on, choose something that’ll like, and head on down. Tip: Go for balcony seats for the full effect!
11. Have a drink at The Manchester
The Manchester is a good old fashioned British pub located in Downtown Windsor. It serves up great food, most of which are named after British icons (like the Big Ben Burger), which is cool and all, but the wooden interiors are definitely something that gives it a lot of character.
Find a spot inside, or out on the patio, order your beer and then people-watch for the night. Best enjoyed with friends or by couples, having a drink here is easily one of the best things to do in Windsor, Canada at night. Look out for the red phone box, too!
Where to Stay in Windsor, Canada
Looking for a specific place to stay? These are our highest recommendations for places to stay in Windsor.
Best Airbnb in Windsor, Canada – Windsorite Apartment Downtown Windsor Canada
This cute little Downtown apartment is just a stone’s throw from the centre of all the action in the city. Naturally, it’s close to a whole load of bars and restaurants, as well as the riverfront itself – including Dieppe Park. This spacious, modern apartment is all about its open plan living and features a queen sized bed, a pull out sofa, a fully equipped kitchen, laundry facilities and – to top it all off – its very own garden!View on Airbnb
Best Hotel in Windsor, Canada – Four Points by Sheraton Windsor Downtown
Clean and new, this hotel offers up stylish settings and neutral decorations – and is (most importantly) great value for money. There’s an indoor pool, a cool lounge bar to hang out in, and even an outdoor terrace for city views. From here it’s easy to stroll to pretty much anywhere in the Downtown area, giving it a pretty awesome location. Easily the best hotel in Windsor, Canada.View on Booking.com
Romantic Things to Do in Windsor, Canada
In case you are headed to Windsor, Canada with your partner, or in case you bag yourself a date with a local, here are the best romantic things to do in Windsor, Canada!
12. Get arty at the Art Gallery Of Windsor
For one of the more artsy things to do in Windsor, Canada, taking a stroll around the Art Gallery Of Windsor this is the obvious choice. If your partner is into art then great. If not, then impress them by pretending that you are!
Established in 1943 and set in a Modernist building, the Art Gallery Of Windsor is all about showcasing local and regional Canadian artists. It may therefore throw up some surprises if your art knowledge extends only to Impressionist classics. Definitely a pleasant surprise of a gallery and one of the more unusual things to do in Windsor, Canada.
13. Spend the day at the beach
What could be more of a romantic thing to do in Windsor, Canada than spending the day at the beach? Not many more things, we’re saying (especially in summer when it’s hot). So we’re saying, when the weather’s good of course, that heading to Sandpoint Beach if you’re in town with your partner.
There’s a lifeguard in the summer, beach volleyball, and concession stands where you can grab a snack or two. Most of all though, we imagine you’ll be wanting to spend time just lying next to each other on the sand, chilling the heck out, soaking up the sun and letting the sounds of summer waft over you. It’s made even better with a picnic and a sunset, of course!
Always Be Insured
Don’t forget to sort your travel insurance! We’ve put together a roundup of the best travel insurance for backpackers, or if you’re low on time, get a quote from World Nomads now, our favorite travel insurance provider.
Best Free Things to Do in Windsor, Canada
In case you are on a tight budget, there are plenty of free things to do in Winsdor. Broke Backpackers rejoice!
14. Walk around Windsor Sculpture Park
A museum without walls, Windsor Sculpture Park is home to 31 large scale sculptures and makes for a very decent free thing to do in Windsor, Canada. Created by internationally renowned artists, the works on show here add colour and vibrancy to the lakeside waterfront.
Some of the pieces you’ll see include Pouta Saila’s “Dancing Bear”, “Business Man On A Horse” by William McElcheran, and “Flying Men” by Elizabeth Frink. Any fan of art, or even anybody just wanting somewhere cool to stroll around, will enjoy ambling around this interesting park.
15. Stroll around the old Walkerville neighbourhood
Walkerville was incorporated into Windsor in 1890. Interestingly this place was actually a model town, owned and created by Hiram Walker – the same guy who owned the Canadian Club Whisky. And discovering it is definitely one of the more off the beaten track things to do in Windsor, Canada.
Walkerville was his vision for a neat community: he built houses for his workers, churches, a school, and other community buildings. Though incorporated into Windsor itself, you can still see the “ideal” character of the area with its wide streets and large houses. There’s a Walkerville School, even, which is located next to Willistead Manor.
Windsor Packing List
1. Travel Water Bottle: Always travel with a water bottle – it’ll save you money and reduce your plastic footprint on our planet. AR bottle are tough, lightweight and maintain the temperature of your beverage – so you can enjoy a cold red bull, or a hot coffee, no matter where you are. For every AR bottle sold, we donate 10% to PlasticOceans.org – an initiative to reduce plastic in our oceans!
2. Microfibre Towel: It’s always worth packing a proper towel. Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight and can be used as a blanket or yoga mat if need be.
3. Security Belt with Hidden Pocket: I never hit the road without my security belt. This is a regular looking belt with a concealed pocket on the inside – you can hide up to twenty notes inside and wear it through airport scanners without it setting them off. This is hands down the best way to hide your cash.
4. Camera or Cell Phone Camera Accessories: One thing’s for sure – Windsor is a picturesque destination! Get perfect shots from your phone using clip-on-lenses with wide-angle, close-up and optical zoom. With the ability to turn travel pictures from basic to professional, this universal lens sits neatly over any phone camera and comes with a durable, travel-friendly case!
5. International Adapter: Windsor outlets accommodate typical US two-pronged plugs, but for electronics that have three prongs or if your plugs are of a different variety, you’ll need an adapter. Save yourself the hassle of trying to track down an adapter at your destination and paying twice as much than planning ahead by buying one online.
Books to Read in Windsor
These are some of my favorite travel reads and books set in Canada, which you should consider picking up before you begin your backpacking adventure…
The Backpacker Bible – Get it for free! Learn how to ditch your desk and travel the world on just $10 a day whilst building a life of long-term travel with an online income. To inspire and help the next generation of Broke Backpackers, you can now grab ‘How to Travel the World on $10 a Day’ for free! Get your copy here.
The Handmaid’s Tale – An acclaimed novel that takes places in a futuristic and dystopian New England. Now a popular TV show.
Beautiful Losers – Musician/writer Leonard Cohen’s final novel. Highly controversial and very experimental in nature.
Sunshine Sketches of a Little Town – A series of short stories that take place in Mariposa, a fictional town set in Ontario.
Best Things to Do in Windsor, Canada with Kids
Travelling with kids can be a challenge. Our list to the best things to do in Windsor with kids will help keep them entertained though.
16. Check out the planes at the Canadian Historical Aircraft Association
You’d be hard pressed to find a child you won’t be completely enthralled by any sort of vehicle: we’re talking trains, automobiles and – in this instance – planes. The Canadian Historical Aircraft Association shows off a whole bunch of vintage military and civilian aircraft for easily one of the best things to do in Windsor, Canada with kids.
Open from 10am to 3pm, this museum is a place where your children can learn about Canada’s historic aircraft; go on a guided tour to get the most out of it, seeing everything from biplanes to bombers. It’s perfect for children – they will even be able to get into some of the planes themselves. And there’s a gift shop. It’s a wonderland!
17. Splash about at Adventure Bay Family Water Park
Adventure Bay Family Water Park is an indoor water park that’s good for year round fun splashing around in a whole load of different pools. It’s a perfect thing to do with your family when you’re in Windsor, Canada – and it’s a great idea to do when it’s raining since you won’t have to worry about the weather!
It’s good for different ages: smaller ages of children will love the Tot Loch Splash Zone (complete with a tipping bucket and bubble jets), whilst bigger kids will enjoy the Master Blaster Water Rollercoaster and Wave Pool. Everyone, of course, will love the Wave Pool!
Day Trips from Windsor, Canada
Windsor is a surprising place, packed full of more interesting things to do than you would have originally thought. However, being located in quite a scenic part of Canada – with Lake Erie and other spots just on the doorstep – it would be a shame to visit this area without exploring further afield. So to show you just how cool it can be to get out there, here are a couple of good day trips from Windsor, Canada.
Take a trip to Fort Molden
The National Historic Site of Fort Molden, located a 35 minute drive from Windsor itself, is an interesting place to visit. Built in 1795 by the British, and the site of some important meetings between leaders during the little known War of 1812 (fought between the United Kingdom and the United States). A British stronghold during the war, it’s a good place to learn about Canada’s early modern history.
Formerly, Amherstburg Fort, there are a fair few things to occupy your time here. You’ll get to go inside the barracks, dating back to 1819, to see what life would have been like for a soldier on what was called the Detroit Frontier. You’ll also get to learn how this became the site of the longest American occupation of Canadian soil. It was also the terminus of the Underground Railroad for slaves escaping the States.
Discover the Southwold Earthworks
For one of the coolest day trips from Winsdor, Canada, and to soak up some history of the area that doesn’t involve rival New World colonies and countries, make a beeline to Southwold Earthworks. This area is where the earliest inhabitants of Canada once lived, from 1500 to 1650. It’s where indigenous, pre-contact people Attawandaron lived in longhouses behind palisade walls.
It’s a fascinating place to come to learn more about the history of what the culture and past of the land would have been like before the arrival of Europeans. Not only that, but the oval shaped village (you can still see the shapes of where people would have made their longhouses, and the bump of the wall surrounding it) is a tranquil place with a serene setting. All this within easy reach of Windsor.
3 Day Windsor, Canada Itinerary
Now that you’ve got a whole list of cool, hidden things to do in Windsor, Canada – and even a couple of day trips to get you into exploring the local area – the next task is to figure out how you’re going to fit it all in. We know how much of a tricky task this can be, so we’re stepping in with our handy 3 day itinerary for Windsor, Canada, to help you plan a completely awesome and watertight schedule.
Day 1 – Wind Back Time in Windsor
Your first day winding back time in Windsor and seeing what the past of this Canadian city is like begins with a trip to Willistead Manor. If you’re visiting during summer, that’s great – you’ll be able to wander around (Wednesdays and Saturdays); if not, you’ll have to suffice with taking a photo of the outside of this interesting mansion. Go for brunch afterwards at The Twisted Apron, situated nearby.
You’re already on the doorstep of the Walkerville, a planned town. Continue walking around through this interesting area, making sure to stop by at places like the Walkerville Theatre and generally just admiring the surprisingly modern architecture of this century old town. After this, you may be ready for some more food, so Walkerville Brewery may be a good idea for you. And then…
… It’s on to Jackson Park. Situated about a half an hour walk from the Walkerville area, this is where you can see the QE 2 Sunken Gardens as well as the Korean War Memorial and a number of other monuments. Finish up by exploring The Canadian Historical Aircraft Association and then head back into town for dinner; Bubi’s Awesome Eats in Downtown is a good option.
Day 2 – Windsor: Whiskytown
Windsor is known as “Whiskytown” and that’s for a good reason: there are a lot of distilleries here. But also in the surrounding area are a fair few wineries. Wagner Orchards & Estate Winery is a good place to spend the morning: it’s a beautiful farm where you can get delicious snacks like apple strudel and pick up products like farm fresh eggs. A great way to start the day (come for breakfast, we say).
Back in the centre of town, it’s time to tour around the poutine parlours. Ok, they’re not called that, but it is nevertheless a good time to start thinking about lunch. And after tasting some wine, you’ll be in the mood for poutine – trust us. Try out Frenchy’s Poutinery, for one example – but there’s many, many places to choose from.
Wind up your day with a visit to one of Windsor’s multitude of distilleries for a taste of the city’s whisky. Hiram Walker & Sons Limited is a good place to start, then there’s Canadian Club Brand Centre and the Windsor Club. Once you’ve had enough, you’ll probably want some dinner. Head over to The Manchester for some gourmet pub fare (and drink, if you want to).
Day 3 – Outside in Windsor
You’ll want to start your third day in Windsor with some breakfast before you head out on a day trip to Pele Island. We would recommend hitting up A Dogs Breakfast in the Downtown area for home style cooked morning meals. Then it’s onwards on a day trip from Windsor, Canada to Pele Island – the southernmost (inhabited) point of the country.
Taking around 2 hours to get over to the island, including a boat, here you can spend your time doing a multitude of things. From hiking and splashing around on one of its beaches (if the weather’s good), to fishing and cycling – the choice is yours. Whilst you’re over on the island, you may as well try out the Pele Island Winery. Don’t worry: you can get both wine and food here.
Make your way back to the city for a leisurely late afternoon stroll around Windsor Sculpture Park, soaking up the many pieces of art on show and ambling along the Riverfront Trail with views of the Ambassador Bridge and the Detroit city skyline across the river. Book a show at the much-loved Chrysler Theatre then treat yourself to a whole lot of food at The Bistro at the River.
More Great Resources
Windsor may not be a tourist beacon but this city nevertheless sees a surprising amount of visitors (mostly from their southern neighbours in the US). But this city is indeed a destination in its own right, more than just party central for teens who want to bypass their countries drinking laws: a place of hidden gems and lesser known things to see and do.
That said, you’ll find some good whisky here, with a fair few distilleries to explore; there’s also wineries in the surrounding area. Don’t like drink? You’ll still be able to find a different side to the city thanks to our guide to off the beaten track things to do in Windsor, Canada.
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Chris Lininger is a writer, photographer, and guide from California. He is an advocate for off-beat responsible travel and the preservation of the world’s wild places and spaces. Chris is also a founding member of Epic Backpacker Tours and leads expeditions to Pakistan throughout the year. He is currently riding out the pandemic in Bali. Follow his adventures on Instagram.