We have EXACTLY the same issue. Chicago. Gravel has already started. Road (crit) season starts in like 2 weeks. Runs every weekend from then through first weekend in June.
June is given over to ToAD (Tour of America's Dairyland) in Wisconsin-Chicago's largest suburb, and July is given to the same group with the Intelligentsia Cup. Yay we have 2 good series close to home but it absolutely destroys local grassroots events. Our Illinois Cup is basically over in May.
As a promoter - my date is slotted into the calendar and will never change. The village would never allow a date change at this point. Every other weekend is occupied.
The "pre-cross" ramp up is real. Our first cross race is in August. We have the second or third largest cross scene in the country. We are hosting nationals this year. It's a thing. No one give a flying f about road anymore it seems.
That said we are putting on an actual road race the first weekend of August this year. That should help push the season deeper. There are a couple of races after that but nothing big. Most switch to cross after Intelli. Those still racing road will hit up the Gateway Cup in St Louis in Sept.
What this all amounts to is that my races in May have had sub freezing temps, rain, ice warnings. They have also been 90+ degrees. Our opener the last two years has been everyone in full winter gear. The old opener that I ran for a few years in the middle has been cancelled because of snow on the track that wouldn't melt in time. I have also watched the P/1/2 field race in sleet/ice/snow similar to Gary's pictures above.
Cross has moved to being held during the really hot August/sept/oct months. We often joke in the spring, "Great weather for a cross race" when at a crit and "great weather for a crit race" when at a cross race int he fall. It's asinine but it is what it is. Not going to change any time soon.