Vermont has always had a special, nostalgic place in my heart. I was born and Connecticut and lived there until around kindergarten, and during that time my parents owned a cabin on a small lake called Sadawga. My memories from our weekend trips to that cabin are fuzzy at best, but nevertheless Lake Sadawga had always been a place I had hoped to return to one day.

My childhood best friend, Casey, doing one of her signature dives off the dock at Lake Sadawga. Sometime in the late ‘80s.

The thought of going back to Lake Sadawga hardly crossed my mind until my sister’s wedding in June of 2014. During the reception I had the opportunity to catch up with one of my Dad’s old army buddies, who I knew from childhood as Uncle Randy. Randy still owned the cabin two doors down from ours on Lake Sadawga, and I spent a little time talking to him about my upcoming GAP/C&O Tour as well as memories of summers vacations at the cabin on Lake Sadawga.

As it turned out, Randy is a bit of a cyclist himself, and he told me some great stories about his adventures cycling around Vermont with his wife and his friends. I joked about how much I’d love to bike through Vermont myself one day, and see Lake Sadawga again. Without a bit of hesitation, Randy said

“Well, come on up! Crash at the cabin any time you want!”

My immediate reply was “Be careful! I might just take you up on that offer!”

Now, it’s often that you meet old family friends at things like weddings and graduations, and of course a lot of offers like this are thrown around. But Randy wasn’t just being kind or accommodating — he was more than happy to offer his cabin up without asking anything in return.

Over the course of the following year, after completing the Pittsburgh-DC trip and getting my first taste of touring, I was eager to get out on the road again. I knew I wanted to plan a tour which would incorporate the cabin in Vermont, and as soon as I looked at the basic route from Montreal to Boston I knew I was on to something.

There was one catch: I’ve lived the past 7 years of my life in Chicago, which has the topography of my favorite maple syrup-centric breakfast food (it’s really, really flat). Looking at the terrain maps of Vermont was a bit intimidating to say the least. Other cyclists will probably chuckle at how big of a deal I’m making out of a few small New England mountains, but to me they looked like a force to be reckoned with.

After stressing about it for a bit, I talked with my cycling friend Matt (who is no stranger to mountains — he did a solo tour through Iceland and Western Europe in his early 20’s) and we agreed that it was worth doing. We set a date, bought plane tickets, and there was no going back after that.