Summer Motorcycle Trip With Friends

In August of 2023 I set off on the first real motorcycle trip in years with my two good friends, Chi-Ho and Jigger.

Good friends, moved away

These two lads used to live in Boston with me and we'd regularly get together for weekend rides and day trips. Or just for breakfast, local motorcycle events, or evening drinks out on the town. But they both moved away several years ago, Chi-Ho to North Carolina and Jigger to Toronto.

So a plan was hatched

After a few years of keeping in touch and occasionally meeting up with each other one-on-one, we decided to finally arrange a reunion motorcycle trip together.

Day 1: Setting off

I rode solo from my home in New Hampshire to Syracuse, New York. Chi-Ho took two days to ride from his home in Raleigh, North Carolina to meet me there. He was already at the hotel when I arrived soaking wet from spending half the day in heavy downpour.

Chi-Ho showed me his boot drying trick - shoving the hotel hair dryer into each boot for 15 minutes at a time, which promptly stunk up the entire room. After a chill dinner out at the famous Dinosaur Bar-B-Que, we settled into our hotel for the night.

Day 2: Crossing into Canada

The next morning we set off together to ride from Syracuse to Jigger's home in Brampton, Ontario, just outside of Toronto. The chosen route took us over the border into Canada via Niagara Falls.

It was a hot day with a lot of traffic getting into Canada and then through Toronto into the suburbs. But we made it to Jigger's house and then went out for dinner together.

Day 3: Exploring Toronto

We spent a beautiful sunny day taking the train into downtown Toronto and walking around, getting coffee, snacks, etc. That night we had a nice Indian dinner at Jigger's family's house.

Days 4-8: Riding the Highlands

Then we spent four days and three nights riding the Highland Loop through Ontario's cottage country and Algonquin Provincial Park, staying at little motels each night.

My solo trek home

After a trip full of great riding, good food, and many laughs, I made the solo two-day trek home. I passed through the beautiful historic town of Skaneateles, New York where I stopped to walk around and take some photos.

One more scenic sunset

One more solo evening and one more stop at a cafe in New York for coffee and a muffin, then into New Hampshire and I'm home again.

An annual tradition

After this experience we decided to try to make it an annual tradition to go on a motorcycle trip together.

We made it happen again in 2024, which included a two-day BMW off-road motorcycle class. And in just six weeks we'll be meeting at an AirBNB in Pennsylvania for our 2025 trip.