148 Miles for a Harpoon: My Hardest Day Ever on a Bike

Valentina Rosa, TRA360 founder and CEO (l) with friend Kyle Bettigole at the B2B start line
Valentina Rosa, TRA360 founder and CEO (l) with friend Kyle Bettigole at the B2B start line

This past Saturday I completed my second consecutive Harpoon Brewery to Brewery Ride, the single-day, 148-mile bike ride from Boston, MA to Windsor, VT that Harpoon has sponsored since 2001. Affectionately known to riders as the “B2B”, this ride is not for everyone. To wit, here’s the opening paragraph on the official B2B website:

“The Harpoon Brewery to Brewery Ride is one tough ride. By design, it is not for everyone. This ride is for cyclists who enjoy great beer, are physically and mentally tough, take pleasure in the fellowship of others, don’t whine, excel in the face of challenges, play by the rules, and can ride 148 miles to the finish safely and without their hands being held.”

Oops, they forgot to mention the 6,500+ feet of elevation. Guess they don’t want to scare people away.

I hear you asking, “What, are you crazy?” “YES,” I’d reply, “AND TWICE OVER!”

More than just a one-day bike ride, the B2B is a fundraiser for the Dana Farber Cancer Institute and Team Psycho, Harpoon’s elite triathlon team. So, it’s an opportunity for a physical challenge and giving back. I did this ride for the first time last year with 6 other members of Team Kermit, my Pan-Mass Challenge cycling team. I wanted to prove to myself that in my 50th year that I could take on and complete this ridiculous ride. And, despite a day in the 90+F range with high humidity, I achieved the goal.

2011 was a lot different. Because of the extremely wet spring, I’d logged 100s of miles less than in 2010 and my longest ride of the season was a 56-miler in New Hampshire’s White Mountains. Hillpeats were the norm for the last 6 weeks prior to the B2B but they weren’t enough. I was setting myself up for a brutal day.

Team photo at the foot of the Leviathan, a 7-mile climb in VT
Team photo at the foot of the Leviathan, a 7-mile climb in VT

We rode pretty much as a team for the first 90 miles, though in small groups of 4-3-3. Mile 90 brings on the Leviathan, the longest and hardest climb of the day to mile 98. After that grueling grind, it’s only a half century (50 miles) to be done and dusted. Approaching the last rest stop at mile 125, I got separated from my 3-man team. I knew I was in trouble when the sign reading “Last Rest Stop 1 Mile” was being marched toward the rest stop by a volunteer.

After refueling, rehydrating, and resting for the last time, I asked a volunteer:

“When do we have to arrive at the brewery?”

“They told us 5:00,” she said, staring down at her clipboard.

“Really?” I gasped. “What time is it now?”

“4:15,” she replied without looking up.

WHAT?!?! I quickly calculated the remaining distance…23 miles. Even on our fastest days in a team pace line on flat ground we average 26 mph. How was I ever going to cover 90% of that distance in 45 minutes? Simple answer: I wasn’t. What did I do? I took off.

As if to punish the stupidity of this decision, the skies opened up minutes later and it rained hard for 20 minutes, horizontally a good portion of the time. Getting wet on a bike isn’t that bad when it’s warm. I didn’t have a watch and resorted to looking at my bike computer, counting up to the magic number of 148 miles. At about mile 145 a sag wagon (emergency vehicle) drove by and a guy stuck out his hand with five outstretched fingers and screamed “Only 5 more miles! You can do it.” What? My computer read just 3 more miles and an extra 2 might do me in. This was no stage of the Tour de France but I would finish.

Then, it happened in a few heartbeats later. First, a huge, huge gust of wind so strong it blew me across the road and back, followed in very rapid succession by a downpour and an enormous drop in temperature. “On no,” I said to myself, “could this be a tornado? (Central MA had 7 of them ravage the state in early June.) What about hail?”

BAM! BAM! BAM! BAM! Hailstones the size of peas started falling by the zillions, pummeling my body, and littering the ground. Seconds later the hailstones increased to the size of grapes. Now I’m getting really, really scared and getting pummeled by the hail is really starting to hurt. Desperately looking for help or an overhead shelter, I saw one in the distance, about a 1/4 mile down the road. I put my head down and raced as fast as my legs would carry me. Shelter at last, listening to the deafening din on the tin roof, and hoping it would stop.

Minutes later another rider named Judy pulled into the shelter. She was bruised and bloody, having gone down on the slippery railroad tracks a few miles before. We chatted and waited for the storm to pass. It did and the sun came out. I offered to escort Judy to the finish, now just 2.5 miles away. We made the last climb of 3/4 mile @ 2.3% at 4mph together with Judy on my rear wheel. When we crested the hill we were greeted by this sign: “It’s All Downhill From Here.” We both laughed. “Go in front of me Judy,” I implored, “you’ve earned it more than I have.” She smiled, said thanks, and took the descent. We crossed the finish line seconds apart, smiled broadly and hugged each other warmly, and said at almost the same time: “Great job and see you next year.”

Team photo at the end of 148 miles. How about those smiles?
Team photo at the end of 148 miles. How about those smiles?