ASAP! (or more specifically before November 19th). With this being a very small wedding an accurate headcount is helpful
Of course!
Sorry FL and CA folk but it's likely to be cold (typically 6-29 degrees Fahrenheit). Hopefully there may be some festive snow as well so come prepared! If you are driving from Boston the route is pretty direct and mostly on highways that should be plowed. Having a car with 4 wheel drive would be recommended regardless