A Night Out in Windsor

Downtown Windsor


There’s an often overlooked perk of living in Detroit that most people forget: the ability to flee the country in minutes.

And even if you aren’t running from the law, it’s nice to have the option of hopping in your car and setting foot on international soil on the slightest whim.

While there’s no shortage of things to do in Detroit (more on that soon), the city across the river, Windsor, is also deserving of a visit.

For one, Canadians are the nicest freaking people around, especially our friends Kristi, an incredible photographer, and Greg, a longtime radio personality and DJ. For two, Kristi and Greg are the proud parents of not one, but two Cavalier King Charles Spaniels, which means they are pretty much Penelope’s relatives.

Here’s Katie with their ruby, Ruby:



Unfortunately, Kristi and Greg can’t be your personal tour guides, too (or can they?), so here’s what a sample night out might look like.


Getting there

From Detroit, you’ve got two options: The Detroit-Windsor Tunnel and The Ambassador Bridge.

Detroit Windsor Tunnel  Ambassador Bridge

Moneywise, both will cost you about $5. The bridge, however, will also cost you a little piece of your soul, as it is privately owned by Detroit’s own real-life version of Mr. Burns, Matty Moroun. (We made the mistake of listening to our GPS rather than our hearts on our way home and accidentally took the evil route back.)


What you’ll need

Unless you are from Michigan and own an enhanced driver’s license, you’ll need to bring your passport to cross the border.

If you happen to be traveling with your dog, as we were, you’ll also need a copy of your pup’s rabies vaccination certificate.

The border guards will ask you all kinds of questions: Why are you coming to Canada? How long will you be staying? Are you bringing any guns, knives, bombs, or other weapons? (They’ll try to slip that in coolly.) Don’t be intimidated or nervous. Just answer their questions patiently and they’ll usually let you through without much hassle.


Where to eat

Windsor is known for its Little Italy, dubbed Via Italia. What it’s not known for (at least not yet), is its soul food.

Sweet T's Soul Cookin' Windsor


IMG_4408 IMG_4433

That’s unfortunate, because Windsor is home to Sweet T’s Soul Cookin’which, in turn, is home to some of the best damn chicken & waffles this side of the Mason-Dixon line.

Sweet T's Chicken & Waffles Windsor

Also, Sweet T’s has some incredible jalapeno cornbread (below left) and grit fritters (below right).

Sweet T's Jalapeno Cornbread Sweet T's Grit Fritters Windsor


And, poutine (fries topped with gravy and cheese curds) with crispy fried chicken skin. We’re not even big poutine fans, but this stuff had us saying “holy shit.”

Sweet T's Crispy Chicken Poutine



And you can slather everything in Sassy Sauce.



The interior is really interesting, with a kind of slatted-wood wall extension that’s designed to make the room look even taller than it is.




Where to drink

Head a little closer to the City Centre (those Canadians and their funny spellings!) and drop by the Manchester Pub.

The Manchester Pub Downtown Windsor


This place is billed as “a U.K. pub with a Canadian twist.” (Hint: The twist is that it’s located in Canada.)

It’s a comfortable bar with a hip, young crowd. Then again, considering Canada’s lower drinking age (19), pretty much all the crowds at the downtown bars tend to skew a little younger than those across the river.

Manchester Pub Beer Windsor Manchester Pub Phone Booth


What to see

Finish the night wandering the streets (they’re much safer than Detroit’s) and enjoying the graffiti and well-kempt urban environment.

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Where to stay

We can’t claim to be experts for accommodations in Windsor, because we just stay with our super-friendly Canadian friends. For budget travelers, there’s the University Place hostel, with rates as low as $39 per night.

If gambling is your thing, or you just want something a little classier with a view of the city and/or the Detroit skyline, check out Caesars Windsor Casino Hotel.


Things to do other than drink, eat, sleep, and wander around

Yeah, this post is titled “A Night Out in Windsor,” but if your night out is raucous enough to warrant an overnight room, then you might want some ideas for the next morning.

According to Kristi, five-pin bowling is a thing in Windsor. (I looked it up; apparently it’s a thing throughout Canada.) If you do this, it might be a good idea to befriend a Canadian on the street and then rope them into the game so they can explain the ins and outs. This guy, Bowling Joe, can probably help.

Vancouver BC Joe 5 Pin


If participation isn’t your thing (more of a watcher, eh?), then you can walk on over to Odette Sculpture Park and marvel at the public art.

Odette Sculpture Park Windsor Ontario

Source: ontariossouthwest.com.

Or just head back across the river to Detroit, where we can point you to things to do with some authority.


  1. Sounds like a good time!
    Good thing I have my passport ready!

    • Good info to know just in time for Record Store Day (April 20).

      Thanks for reading!

  2. Windsor is the coolest city in Canada and the best suburb of Detroit. Paris has its Left Bank & New Orleans the French Quarter, but the D goes one better with an international uber-exclusive gated community where casino winnings are tax free (Hail Caesar!) cigars are cuban and strippers actually bare all. Can you dig it? I knew that you could! Y’all come back. Bienvenue!!

    • Haha. Well put, Mark. We’ll definitely be back.

  3. Hi Mark and Katie,

    Great write up! We’re glad you like Windsor. There’s lots more to see and do and hope you’ll come back soon! And hope to meet you some day. Sweet T’s is amazing and you definitely need to check out Smoke n’ Spice (same owners). But beware of the XXX hot sauce. Consider yourself warned.

    There’s lots of great restaurants out in the county too. I would definitely recommend you check out Amherstburg, Kingsville (lots of heritage and connections to Hiram Walker out there), and Leamington’s Bustaurant known as Birdies Perch!

    Keep up the great work!

    Eric 🙂

    • Thanks for the added info, Eric. We’ve been promised at least one more night in Windsor before we move to California. Would love to check out some of these places.

      All these comments only further prove that Canadians are the nicest people!

  4. Mark and Katie

    Thanks for your review of what we all like to think is a pretty cool place to live and work, Windsor Essex County.
    The heritage of our region is the foundation of its personality.You will need to grab a designated driver or tour guide next time over and explore the wineries, take in the Canadian Club Brand Centre tour and of course stop into Walkerville Brewery and the great restaurants of Walkerville to enjoy some Made in Windsor handcrafted beer.Another great beer stop is Motor Burger, they have a nano brewery onsite and are brewing some interesting Ales. Let us know when you are returning, bring some friends and leave the hospitality to us!

  5. Don’t forget to stop at Milk Coffee Bar.
    A cafe that also serves hard to find liquors, it’s featured drink being the ever intriguing Absinthe.
    Live music, Monthly Art show and much more.
    Nurture your soul.

    • Ooooh, our next night out in Windsor could get reallllly interesting with some absinthe.

  6. Glad you enjoyed it here! If you’re ever looking for more stuff to do here let’s us know. You should also look into coming for a visit with he Detroit Drunken Historical Society when we host a Drinks of Walkerville walking tour for them in September.

    • Unfortunately we’ll be living on the West Coast come September, so no walking tour for us. However, we’re already planning our next (and likely last, for some time) visit to Windsor. This time we’d like to make a weekend out of it. Cheers!

  7. Thank you for visiting Windsor and taking in the sites. Hopefully if you get a chance to jump the creek again you can visit Via Italia, many fine shops and restaurants. It also includes Blaks’s Bakery that my family has been operating in the same place since 1918. We still use the original oven my grandfather built in 1918.

    Come on by for the very best donut you may ever taste.

    Looking forward to more of your travels hopefully in the big D, as I love learning about new places. One place you may want to visit is Tom’s tavern on 6 mile it is one of the most interesting bars I have ever been to.

    • Thanks, Tony!

      Mmmmmm, dooooonnuuuuutttsssss….

      Oh, sorry. Got a little drooly there.

      Yes, Tom’s is a legend around these parts!

  8. Oh oh. Typo. Tom’s is on 7 mile.


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