Last updated on February 29, 2024.

Manoli, Aleko, and George picked me up and we began our four hour drive to Windsor, Ontario. Our excuse was to see the Chicago White Sox and Detroit Tigers play at Comerica Park in Detroit the next day. Aleko and I sat in the back seat and played a heated game of Risk on my iPad while George and Manoli captained the ship.

 

Crossing the Border

We drove through the Detroit-Windsor Tunnel and waited in line for the agent to process us:

Border agent: “Why are you coming to Canada today?”

George: “We’re just spending the night in Windsor.”

Border agent: “Nobody goes to Windsor. Seriously, why are you coming to Canada?”

George: “Seriously. To hang out in Windsor.”

Border agent: “Have a good time. Welcome to Canada.”

Detroit-Windsor Tunnel in Detroit, Michigan
Detroit-Windsor Tunnel
Detroit-Windsor Tunnel between Windsor, Ontario, Canada, and Detroit, Michigan
Detroit-Windsor Tunnel

 

Going Out

After that interesting exchange, we entered Windsor and went straight to our hotel, the Holiday Inn (now the Four Points by Sheraton Windsor Downtown). We all took a short nap, got dressed and headed out.

Welcome to Windsor! Ontario, Canada
Welcome to Windsor!

Our first stop was to have a quick dinner and drink at the Whiskey River Speakeasy. It wasn’t bad. They were having their official grand opening the next day. We then walked along the river and admired the views of Detroit across the way.

Detroit from Windsor, Ontario, Canada
Detroit

Walking down Ouellette Ave., our first stop of the night was a country bar, the Bull and Barrel. Personally, I’m not into country, but we had more fun here than any other bar in Windsor. The Bull Girls (bartenders and shot girls) are awesome. We had a lot of laughs with them. If you stop in there, tell the shot girls the Chicago boys said hello (not that they’d remember us!).

We made a quick stop at The Manchester and left after one drink. We walked up Ouellette a little more and didn’t see too much action at most places, and didn’t want to wait in line at the others. Then we “stumbled upon” a couple other establishments that we THOUGHT were worth popping into.

(This part of the night omitted.)

After our little disaster, we regrouped and headed back to the Bull and Barrel at 1am. Once it closed for the night, we decided to get some food and soak up the alcohol before going to sleep.

 

Shawarma Palace

On Ouellette, we stopped at the Shawarma Palace and Pizza Pizza, which are both great choices. We settled on Shawarma Palace. The line was out the door but worth the wait. We each had a chicken shawarma and kibbeh. Excellent. Even better was the atmosphere. Lebanese music was playing loudly, there was a guy playing along on a drum, and people suddenly breaking out into dance.

 

Conclusion

We had a great time and we all planned to make another trip to Windsor when the opportunity presented itself.

Author

Owner of Paisadventure. World traveler. Chicago sports lover. Living in Colombia.

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