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Follow Couple of Yuppies: North American Road Trip

And so it begins: the North American road trip. Toronto has been a great experience for both Jamie and I, but it’s time to turn the page and what better way to do that than setting out on the quintessential North American road trip: the Atlantic to the Pacific. In anticipation of what will be one of the coolest (and longest) road trips that either of us has ever done, we’re breaking down the drive in to an itinerary that everyone can follow.

1. August 31: Toronto ON, Canada –> Huntsville ON, Canada.

Distance: 220 km

Time: 2 hours, 22 minutes

Screen shot 2013-08-26 at 10.22.36 PM

Huntsville is the calm before the storm. This trip is going to be long and hectic. As a result, we will be more than happy to take the opportunity to chillax in Ontario’s cottage country. As the summer heat will still be in effect, we’ll likely manage to grab some sun, sleep on the dock, and hopefully get out on the water. If you’ve never been to Canada’s Muskoka region, you should make a point to do so. As you can see from the picture below, it’s a bit better than a kick in the head, to say the least.

Huntsville Ontario Muskoka Toronto Canada

2. September 3: Huntsville ON, Canada –> York Harbor ME, U.S.A.

Distance: 1030 km

Time: 10 hours, 39 minutes

Ontario Maine

As Toronto to Huntsville is by far the shortest leg of the trip, it’s only fitting that we follow it up with the most gargantuan, painful, I-want-to-pull-my-hair-out-at-the-thought-of-how-long-this-drive-will-be part of the drive. We are planning on stopping in Montreal along the way, visiting some sites we frequented during our university days, only I’m sure we will both be a lot more sober. Upon arriving in York Harbor we will be staying with family and eating as much lobster as humanly possible. Jamie’s cousin is getting married here, hence our reason for driving in the complete opposite direction before heading west to Vancouver.

3. September 9: York Harbor ME, U.S.A. –> Toronto, ON, Canada.  

Distance: 978 km

Time: 9 hours, 13 minutes


This leg of the trip is just a means to an end. We were planning on going through Buffalo and staying the night there, but our friend in Toronto was kind enough to offer his blow-up mattress to us for the night. We took him up on the offer and will be making a pit stop here before taking off the next day.

4. September 10: Toronto, ON, Canada –> Chicago, IL, U.S.A.   

Distance: 837 km

Time: 7 hours, 40 minutes


We are planning on staying two nights in Chicago (one full day). The first night we will be stopping in at Pequod’s Pizza for some deep-dish deliciousness, so stay tuned for our review and interview. Since we are only there for a day we will most likely be hitting up the main sites, and perhaps stop in at a jazz club in the evening. Although we may forgo a jazz club for some grimy drinks and beats in Bucktown.

5. September 12: Chicago, IL, U.S.A. –> Sioux Falls, SD, U.S.A.

Distance: 922 km

Time: 8 hours, 26 minutes

sioux falls

I will be completely honest: I have no idea if we will be seeing anything in Sioux Falls, or just arriving at our hotel and passing out. Again, this stop is a means to an end.

6. September 13: Sioux Falls, SD, U.S.A. –> Rapid City, SD, U.S.A.

Distance: 561 km

Time: 4 hours, 52 minutes

rapid city

Considering this is the shortest leg of the trip, we will be making a few stops along the way. Wall Drug and corn mazes we have been told are two of the most cheesy sights to see, but hey, why not? I’m hoping it will make for some interesting posts/video. Upon arriving in Rapid City, we will then head to Mount Rushmore to see the famous faces of dead Presidents.

7. September 14: Rapid City, SD, U.S.A. –> Calgary, AB, Canada. 

Distance: 1,363 km

Time: 13 hours, 34 minutes


This is by far the longest leg of the trip. If we don’t kill each other first, we’ll be arriving in Calgary late in the evening and staying at Kyle’s parent’s place for a couple nights. Most of this stop will involve visiting family and doing any last minute errands to prep for Southeast Asia.


8. September 16: Calgary, AB, Canada –> Osoyoos, BC, Canada.

Distance: 731 km

Time: 8 hours, 34 minutes


This is another family pit stop, as both of my (Jamie’s) parents live here. Osoyoos is absolutely beautiful, with mountains on either side and a picturesque lake to wake up to every morning. I’ve spent a couple summers here and loved every minute of it.

osoyoos, bc

9. September 18: Osoyoos, BC, Canada –> Vancouver, BC, Canada. 

Distance: 396 km

Time: 4 hours, 40 minutes


vancouver mountains

Finally, after driving clear across the country, we will be arriving in Vancouver on September 18th, giving us about five days to prep before taking off to China on September 23rd. Needless to say I’m sure we will be somewhat exhausted by that time, however the thought of taking off traveling for six months is sure to give us some much-needed energy. The true test is whether or not one of us actively tries to push the other one out of the car before then, but more on travel tips for couples later!


  1. Holy shit you guys are going to be busy. Have tons of fun! Looking forward to seeing the pics and vids!

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