I think that you need to take advantage of any decent weather for riding during the summer. Here in Virginia, it becomes very humid and more evenings than not, there is a real chance of thunderstorms. The past couple of weeks have been exactly that way- warm and humid with thunderstorms int he evening. I've been able to get rides in about 60% of the time, which is good. The days are long this time of year, and you don't have to worry about riding in heavy jackets.
The 1940 Westfield Sports Roadster is an outstanding bicycle. It's somewhat basic and in some ways primitive, but it's fun to ride. The fun comes from the simplicity. The bike is reasonably light and very docile in handling.
Pretty much anyone could ride this bike hands off without difficulty. I'm really enjoying this one. It's a great, American bike for Fourth of July weekend.