My impression is that the largest face-to-face conclaves of 50+ers have been the Annual Rides, and I had the opportunity to attend the Second and Third in the New York Finger Lakes Region and in Michigan respectively. There were about 10 subscribers in New York, and about eight in Michigan. Depending on how avid the posters, it can be almost surreal to meet these E-acquaintances in person, but always have been very pleasant experiences meeting those who share the common ground of the Fifty-Plus Forum.

FYA, there is a sticky on the Fifty-Plus Forum, A Chronicle of the 50+ Annual Rides, and in one post, I listed the threads that chronicled the Rides II to IV beginning with the personal narratives and photos:

I have proposed a Fifth Annual Ride in the Boston area on July 27 (see below). In previous years suggestions have been made for multiple rides in various areas of the country. Usually the Annual Rides (Second to Fourth) had been held in conjunction with an organized ride by a cycling organization. Your Social, as well as a ride proposed by Barretscv in Wisconsin are the only independent ones I've read about since reading this Forum since about 2010. Best wishes, and apologies to the OP, NOS88, for segueing into this off-topic pitch.