That said, I'm no stranger to ascending hills on a bicycle. I've tried Hurricane Mountain Road (in North Conway) after riding Bear Notch Road (and did another 20 miles to meet friends and then swim at Echo Lake State Park). I have toured (solo, self-supported) in Colorado, riding over several 10,000 plus feet passes. And I have generally tried hill climbing in several places (and wrote some advice on speeds on descents of these hills). One thing that sticks with me is that ascending hills can be hard and hills can be relentless, or worse if you aren't in shape or don't know what to expect. I recall ascending Monarch Pass in Colorado on a solo tour. I was told by locals that, despite what my map said, there was a campground on the west side of the pass. That wasn't true. I mashed my pedals up to the summit, arriving after sunset, looking for suitable places to pitch a tent near the road. Not surprisingly, there wasn't any place to put a tent until the campground on the other side. I succeeded in riding to the summit of the pass but it wasn't easy and it took reserves of energy I wasn't sure I had. Using reserves of energy was true when climbing to Hurricane Ridge and Obstruction Point in the Olympics and any number of other high points I toured over.
It's similar when riding without gear, especially when your gearing isn't the best for the situation. I opted for a compact crank on my Independent Fabrication along with a 12/25 rear chain rings. That works pretty well for me, much better than the 39/52 cranks with 11/23 rear chain rings I used on my Lemond Alpe d'Huez. In spite of the latter gearing, I made it up a lot of steep hills in western Massachusetts, Vermont, New Hampshire, Mount Cadillac in Acadia National Park, and the first 30 miles of the High Road to Taos out of the Santuaria de Chimayo on my Lemond. Given that I would have the IF well into my fifties and even my sixties, I thought I would appreciate the compact crank eventually. I did appreciate it on the Hurricane Mountain Road ride, which I did four months after I started riding my IF. I will make some adjustment to the IF for the High Point ride but am not yet sure what it will be.
Given that little bit of history, I am taking the High Point ride seriously. The distance is likely to be unremarkable for me by the day of the ride - my average ride length on my IF is close to 50 miles and I have done several rides longer than that and have several more planned. But the High Point ride will consist of a hilly ride to the base of Mount Greylock and then the 2700 foot ascent to the summit. That's a hard ride and I'll have to (or get to) do the reverse the next day. At least the second day is likely to end with a downhill run rather than a very steep ascent.
I'm pretty familiar with cycling in western Massachusetts and could put together a decent ride from the valley to Greylock myself. But the shop has at least one person there who I would trust more than me to make a great ride in western Massachusetts, even if she might not understand what some of us would call gratuitous climbs.
50 miles with 2100 feet of climbing
56 miles with 2500 feet of climbing
22 miles with 1300 feet of climbing
66 miles with 2900 feet of climbing
50 miles with 2200 feet of climbing
Plus one commute to work and one errand on the hottest day of the year. The mileage is getting there but I need to add in more hill climbing. I'm considering heading out to western Massachusetts to ride in the hills at least once before the high point ride. And I will continue to ride as much as I can until then and will slip in 4-6 sets of 5 ascents of the local training climb. I did the 5 ascents (about 1600 feet of climbing) a couple of times before the 2009 D2R2 and I was fine on that ride (100k, 8000 feet of climbing, much of the climbing on dirt roads). Whether this is enough to enjoy the Greylock ascent won't be known for 3 weeks.
Early morning start, in Concord before 6:30AM:
Sherman Bridge, Sherman Bridge Road, Wayland (Sudbury is to the left, Wayland to the right) - I was here on June 1st and 2nd (note the lights on the bike, necessary for the early starts):
Nagog Hill Farm, Acton, MA at 7AM:
Snapping turtle, after crossing Lincoln Road, just west of Sherman Bridge, Sudbury. The shell was about 14-16 inches long. So why didn't the turtle cross the road under the bridge?
Mileage for the year: 994.