There was a group from BF, C&Vers mainly, who used to do the Dairyland Dare on vintage bikes. That group fell apart plus COVID hit. I need to think about doing that ride again. It's easy drive for me to the start in Dodgeville, WI, and the terrain is a challenge. I do the 100k which has around 5,500 ft of climbing. There are a lot of hills in SW WI. Maybe it's time to get my '78 Trek TX 900 road worthy again,
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https://dairylanddare.com/
I really like BAM, Bicycling Around MN, but that canceled this year again. COVID really interrupted that ride.