Day 1, 86 miles, Easthampton, MA, to Milford, CT
In almost every adventure I’ve embarked on, Day 1s have been awesome. Day 1s are full of hope, possibility, optimism and energy.
This Day 1 was no different.
I headed south out of Easthampton, on the Manhan Bike Path, at 7:30 a.m. A cold, gusty wind smacked me in the face most the morning, and my fully loaded panniers and bags act like a sail, catching every breeze.
But it didn’t matter. I was on my way to the unknown. I mean, not completely unknown because I do have a route and a plan. But I mean the unknown as in the day-to-day: who I might meet, what I might see, amazing and weird scenes I’ll happen across, and, inevitably, setbacks and triumphs.
A couple hours later I crossed into Connecticut, on the Farmington River Greenway bike path that starts in Westfield and goes all the way to Farmington. The sun was out (wind still blowing hard!) and I was making good time. By noon I crossed the Farmington River and it was turning into a gorgeous afternoon.
For this route, you get off the Farmington River bike path and ride on roads through Southington, CT, which is a nice town but has an eyesore stretch of road with every fast food and big box chain you can think of, and a lot of traffic. The payoff to surviving that turnoff is the New Haven-Northampton Railroad Canal Line, an awesome bike path that runs from Southington to Yale U. in New Haven. I definitely recommend this bike path– very smooth, lots of good restaurants right alongside, wonderful atmosphere. 
I left the trail and headed through downtown New Haven, then out to West Haven for a great stop at the beach and a freezing plunge into Long Island Sound. The idea here is a Day 1 plunge in Long Island Sound, then a much more pleasant plunge into Long Beach to finish. Get it? Long Island, Long Beach? (It’s the little things.)
So after about a year of planning and a few months of cold rides on nearly every road in the Valley and beyond, this Day 1 was a welcome end of the preamble and a beginning of the actual journey.
One thing I’ve learned though: you can’t depend on Day 1s. They’ll trick you into believing the entire adventure will be like the start, and that you’ll always have the energy for it that you do today. We adventurers well know that is not the case. There will be slogs in the future, of that I’m certain.
So I’m saving this Day 1, and hoping to extend the feeling as long as possible.