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The first time Jono ran this route, he expected it to be about half its actual length, based on a terrible, terrible underestimation from looking cursorily at the [[North Berkshire Trails map]] provided by the [Williams Outing Club WOC]. As the time wore on past 2 hours before he reached the summit, he began to get suspicious. Having finally conquered the summit and slogged back down the route almost totally exhausted, Jono arrived back on campus after nightfall. He missed dinner entirely. Two days later, he set out on his [[WOOLF]] trip and for the next three days hiked a route with shorter total mileage than he had run on the one day.
To prove to himself that it wasn't just a fluke that he had survived a run twice as long as his previous longest route, Jono determined to complete the run again in the spring. He succeeded, and thus began a twice-yearly tradition of THE Greylock Run. Notable subsequent THE Greylock Runs include the one in
[[Fall 2004|fall 2004 ]], when Jono, now on the [[Cross Country Running|cross country]] team, ran THE Greylock Run on the same day as the rest of the team ran a tempo workout on the mountainous uphill section of the route. He met them at the summit, got in the team picture, and headed back down at a somewhat desperate clip (sub-7:00 miles) in order to get to [[Greylock Dining Hall|Greylock DH]] (appropriately) before closing time at 8:00. He made it to dinner but wore down his legs, which may have affected his racing performance later in the season.
In order to avoid this unwanted consequence of THE Greylock Run in fall 2005, Jono decided to schedule it for after his racing season, and for the first time invited all other team members to join him. The run, completed on 6 November
[[Fall 2005 |2005]], coincidentally the same day as the [[Schnellstiegen]], was a smashing success, with three other XC runners, Ryan Ford '09, and Owen Martel '09, joining Jono for the entire run and surviving. This latest iteration of THE Greylock Run featured a variation in the route, namely substituting the [[Appalachian Trail|AT]] and [[Guide to Hiking#Bellows Pipe Trail|Bellows Pipe Trail]] for the steep downhill parts of [[Notch Road|Notch Rd. ]] Despite leaf-pile trail conditions, fog, cold, and sprinkling rain, this route proved a smart alternative to the leg-pounding standard route, also conveniently cutting the total mileage down slightly. Now that it is no longer a solo effort, there is great hope that THE Greylock Run will become a continuing hardcore Williams tradition.