Are we talking events in general, or just AK gatherings?
If AK, then from Peekskill to Clinton MA, for Frankenfests, about 3 hours each way.
For concert events, one weekend my brother and I traveled from upstate NY to Washington DC for two Dead concerts that weekend. At the time, I was driving a 1969 Impala convertible, red, white top, black interior with bucket seats, console with the horseshoe shifter. Top down of course! There was a deadhead caravan all cruising along together. At one point along the way, we were alongside a Harley, the girlfriend was the passenger, she smiled, and lifted her shirt for us to take a gander at her ample chest! Then she told her bo, and he laughed, gave us the thumbs up, and we kept on going! So I'd say we probably covered 800+ miles that weekend.