One of the key things that has helped me maintain my 60+ pound weight loss, aside from riding in general, is my annual bike tour. Planning a long ride, training for it, and (gulp!) actually doing it give me an annual boost of motivation. As I've gone from year to year, I've gotten more ambitious in one way or another. The 2010 ride was along the GAP and G&O trail from Pittsburgh to DC; 2011 saw me in Quebec;in 2012 I tried on hills on a group ride in the FingerLakes. Two years ago I bit off more than I could chew when I tried Skyline Drive in the Shenandoah mountains. And last year, I had a wonderful group trip in Washington State.

This year, as I reached the birthday milestone that lets me post in a different forum just a few letters down the alphabet from "Clydesdale", I got a bad case of ambition. I wanted to try hills again, AND I wanted to try another unsupported tour. I decided on one of the goals for the tour back in December, when as part of a holiday promotion by the game Cards Against Humanity I received a square foot of an island in Maine. Visiting my newfound "estate" would be one end of the tour. The goal on the other end would be a campground in New Lebanon, NY, where friends of mine have an annual weekend-long party featuring music, friendship, and 100+ flavors of homemade ice cream. In between would be about 350 miles of Maine, New Hampshire, and Massachusetts -- including the Berkshire Mountains.

Or, as it appeared on RideWithGPS:


350 miles and 18000+ feet, unsupported -- this could be something to have a Round Number Birthday with.