I really like the Around the Mountain in 80 Days idea! Here are some more suggestions for your consideration around this event.
1. Consider two levels of participation - one for only paved airports and the other is paved airports PLUS a number of Vermont's wonderful grass strips.
2. Consider rewarding every participant who completes either level with a really cool t-shirt, like the last one!
3. The concept of a single winner who is the FIRST to complete either level might incentivize one to fly in less than safe conditions. Not what we want. Therefore let's reward everyone who completes the task within the allotted timeframe (80 days?) with a cool t-shirt and come up with a special prize for some other criteria. I have some ideas for those criteria (see below). The prize could be a special trophy that the winner gets to keep at their home airport FBO for the year.
4. Special prize winner ideas.
a. We can stick with a prize for the one who finishes it first, but I think that might be incentivizing questionable decisions.
b. How about if the winner is the home airport of a team of winners. The winner could be the airport with the most aircraft that complete the larger list of ALL Vermont airports, including grass. That way, it would incentivize teams to include taildraggers / grass capable aircraft as well as fancy fast flyers. Obviously airports with more airplanes based there are favored in this competition, so we need a way of equalizing that. What about calculating participation factor, i.e., number of planes from a home airport that complete the task divided by the total number of airplanes based at that home airport? That way, an airport with 100 planes based there and 10 complete the task, (10/100 = .1 or 10%), is on an even footing with a small airport with 10 airplanes based there and 1 that completes the task (1/10=.1 or 10%). The airport with the highest percentage of planes completing the task wins the right to keep the trophy for the year at their FBO.
c. Some other ideas?