Yeah I tow my dads ~3500 lb boat all the time with my blazer no sweat

 

This time of year in upstate NY, I think you'll be fine. The main things to be concerned with are #1: tranny temps, & #2: engine temps.

Except for the past couple warm days, this type of weather is good towing weather - read: danger free.

 

Thanks everyone for the responses. Didn't want to do something stupid and end up hauling them both to the crusher.