Two team members join a few friends, load up their road bikes and trade watts for wanderlust, finish lines for fly storms and crits for the countryside on an unforgettable four-day bikepacking trip from Portland, Maine to Poughkeepsie, New York. As recounted by Chris Burati:

Bike racing takes over much of one’s free time from March until September. If it’s not endless hours spent training, planning, tinkering with the bike, working on team duties, and racing, it’s sleeping, eating, working, and thinking about bike racing. If one partakes in the art of cyclocross, you might as well be racing year-round.

When Mat Street approached me last year with the idea of touring from Manhattan to Vermont to see the fall foliage, we were both slaves to bike racing and just couldn’t make the time to do it. Fast forward to 2016, when it was the "Summer of Mat" (for those Seinfeld fans out there). Given his impending relocation to India, we decided we had to make the trip happen as friendship and the scarcity of time easily eclipse a season’s bike racing goals.

So we planned the trip, and what started out as a Mat and Chris departure from Manhattan at 5 am with the intent of riding to our friend Joe’s house in southern Vermont, became a tight knit group of friends riding 450 miles from Portland, Maine to Poughkeepsie, New York over four days during Memorial Day weekend. We came away with timeless memories, stronger bonds, and very tired legs. Most important, this trip helped me rediscover the joy of cycling and the unparalleled freedom a bicycle provides.

When taking a one way bus trip to reach the starting point of your tour, it is important to pack light and use every available nook and cranny of disposable cardboard bike box. Lastly you must build your bike in the parking lot of the bus station. There is simply no other way to do it.

I arrived in Portland in the wee hours of the morning from Europe where I had spent the week on business travel. Despite the jet lag, late arrival, and early wakeup, I remained eager to roll with the crew and begin our journey. A mere few hours later I was feeling the week of food and drink Amsterdam and London had blessed me with as well as the jet lag.

Day 1’s feature was the Kancamagus Highway, a long climb through the beautiful White Mountain National Forest. In order to reach our lodging on the Vermont border for the night, we needed to pass through the area in the unseasonal heat with little food and water in our stores. This small forested lake was found right before the long descent into town, and offered a brief respite.

Day 2 was spent on endless dirt roads traveling from the New Hampshire-Vermont border to Killington. Mat’s face says it all.

This gem of a house appeared off of a dirt road in the middle of nowhere. It was decorated in colorful trinkets ranging from household items to pop culture symbols from the last four decades. While it looked funky and avant garde, there was a menacing air about it, and we decided to move on quickly after Mat got a snap of his bike in.

Day 2’s feature was Roxbury Gap. Roxbury is not the most brutal of the Gaps, but it is a Category 2 dirt climb with pitches topping out at 11%. We suffered on this climb, especially with relatively heavy packs and fatigued legs, but were rewarded with a thrilling descent and the chance to escape the maelstrom of black flies that flew thick around the summit.

We were also rewarded with this wonderful creek found behind a general store stocked with locally grown food and topped off with a deli. Not pictured: the band playing classic country rock tunes on the porch outside. After the dip we proceeded onward to Killington where we had a Taylor Phinney sighting, I bonked hard, and we ran into our friends who had just finished racing Stage 1 of the Killington Stage Race.

Riding out of Killington on Day 3 we were escorted for the first 30 miles by Pat Torpey. He was one of a few special guest stars we had over the course of the trip and a refreshing addition to a group that had already ridden 230 miles together.

This sums up Day 3. The main feature was a very short, punchy, loose rock climb through a state forest followed by a long sketchy descent. I made it up the climb OK, but flatted shortly into the descent. Three flats and two black fly swarms later (this is in less than a mile) I was hitching a ride with a local down to the bottom. Here I am changing my third flat out of reach of the black flies. Right after this change, I flatted again. Mat was a saint for putting up with this and toughing out the fly attacks. There exists somewhere a video of us jumping around, swatting at the flies before things stop being funny and I start bleeding from the bites.

Despite the flats, we made it to Joe and Margaret’s beautiful house in Pownal, Vermont before sunset where we were greeted by this breathtaking view and an amazing vegetarian meal. We slept well that night with full bellies and the sound of the rain's soft patter outside. Only 120 miles to go on our final day and this unforgettable trip would be over.

Day 4, Memorial Day. We got a late start given how peaceful Joe’s house was. A large breakfast greeted us when we awoke, and once consumed, we saddled up and were guided by Joe to Williams College just over the border from Pownal in Williamstown, Massachusetts. Joe gave us a tour of he and his wife Margaret’s alma mater. There, we bore witness to the town’s Memorial Day parade as we departed.

Day 4 took us through the idyllic Western Massachusetts countryside and past bucolic towns such as Great Barrington and Stockbridge. This region is especially close to my heart as it’s where I grew up, and it was great to experience it by bicycle, which has been a rarity in the seven plus years I’ve been riding.

The last leg of Massachusetts was Bash Bish Falls State Park, a leafy winding partially paved, partially dirt route that drops straight into Taconic State Park on the New York side of the border. After fueling up in Copake we proceeded south towards Poughkeepsie. This is where the picture taking ended, the faffing subsided, and the hammering for the train station began.

450 miles. We made it to Poughkeepsie. Despite being welcomed by gunshots, we comfortably made it onto the train with beers in tow. The only thing left to do was reflect on what we'd just experienced during the two-hour train ride home.