... Chicago is called, "The Windy City" for a reason.
This could be a balmy spring day in April that started out in the mid 60s (F) and a squall comes up with the temp dropping to 40F!
The OP photo was Boston, but I get your point.
We just had such a weekend here in Chicago. Friday was 80+, Saturday dropped to 46-48, with chill factor in the mid-30s. Completely ruined the first art fair of the season I had. Rainy, windy and cold the first day, with the ratio of artists to (brave) visitors about 10:1, got cancelled mid-day. Got a call from the security that my tent was damaged and to come fix it. Drove back 46 miles to find the tent actually ok, just a rack with matted prints on the ground, inside the tent. Removed all the art from the walls, packed it into the car and drove back home. Next day, Sunday, started without rain, but still windy and at 46 F. Tents in my raw were either packing, gone or never showed up, leaving me alone and totally exposed to the wind from any direction. So I packed and left too. Few visitors, a couple of compliments, zero sales and a couple of hundred dollars print damage, not to mention a wasted art-fair fee.