We are looking into the possibility of doing a group drive on the Mt. Washington Auto Road on Saturday evening. Stay tuned...
PS - not sure if that would replace or be in addition to some sort of scavenger hunt (perhaps geocaching)... Still working out the details.
IMPORTANT(!): IIRC, the Mt. Washington Auto Road closes and locks up around 4 or 5 PM in the afternoon. The road is private property. Have you made special arrangements with the Mt. Washington Auto Road people to be open after-hours? If not, the group drive needs to happen in the early MORNING.
It would be about an hour drive to the mountain from TDIfest, then probably a half hour or so to get organized at the gate, then it's an 8 mile ride up the mountain at 15-20 MPH all the way up in first gear, taking about half an hour.
During the climb, keeping the engine RPMs in the 2500-3000 RPM range in first gear works best. If another car is behind you and wants to go faster, pull over at the nearest turnout area (plenty along the way) and let them pass. Also cars coming down the mountain are required to yield to cars coming up the mountain when encountering each other in the narrow spots. First gear is required to climb efficiently and 15-20 MPH is the recommended speed by the Auto Road and puts the engine in the 2500-3000 RPM range. Staying in this range avoids the risk of turbo surge at high altitude and keeps EGTs under control. When you get to the parking lot at the top, leave your TDI idling for several minutes with the cabin heat cranked and fan on high because the engine will be thoroughly heat soaked at the end of the climb.
For people who have never driven up Mt. Washington before, the drive is not for the faint of heart or if you have a fear of heights. The Mt. Washington Auto Road is steep, narrow, winding mountain road with steep dropoffs in some areas and no guardrails. The road alternates between paved and dirt road sections in a few areas. Then there's changing weather conditions that factor into it. There's a short but serious climb (18% grade) at the top to enter the parking lots at the top. The drive can be somewhat nerve racking the first time you do it. Some people may not appreciate the driving experience. There's a big warning sign at the entrance that talks to this. Fear not, TDIs were born to climb these kind of hills due to the TDI's torque characteristics. The drive overall is a beautiful drive and a drive like no other.
Coming down the mountain requires staying in first gear and staying off the brakes, touching them only occasionally when needed. A technique I found works is to come almost to a complete stop right before a sharp turn then let the car gradually speed up again on its own while idling in first gear. If another car is behind you wanting to come down faster than you, pull over at one of the turnouts along the way and let them pass. The last time I was coming down the road, I let somebody in a Honda Pilot go by me and I could definitely smell their VERY HOT brakes as they went by. If it were at night I probably could have seen them glowing red-hot in the dark.
When you finally get to the bottom and get out onto Route 16 again, you need to get on the power and accelerate at WOT for several seconds. Your TDI may smoke a lot but it is needed to get rid of oil accumulated in the intercooler and exhaust system after 8 miles of engine braking while coming down the mountain.
It's best to get up there in early morning. If it's clear day at the summit you can look across Maine and see the Atlantic Ocean on the horizon. If clear enough and sunlight is just right, you can see the glitter of sunlight reflecting off the ocean waves. Looking to the north, you can see up into Canada. Looking west, you can see across Vermont and into New York. You can see much of New Hampshire looking to the south but a few nighboring mountains get in the way. On a crystal clear day (very rare) you can see the Adirondack Mountains in New York 130 miles away, the furthest points visible from the summit.
Just my $0.02 FWIW from having driven the Mt.Washington Auto Road several times.
I'm interested in the drive and looking forward to it.