Dates can vary for me depending on my own kids schedules.
As for routes, there are a number of great driving roads in north western CT (Litchfield Canaan etc) that I enjoy driving on. ToyMakers Cafe 85 Main St, Falls Village, CT 06031 (North of Limerock) - is a great place to stop in for lunch (covid dependent). They usually cater to the car/ motorcycle enthusiasts.