Do you still live nearby, MLC? I've been in Torrington for 3 years since moving back from Colorado (I'm from CT originally, but East of the river), but most activities take me towards Hartford, so I haven't gotten to know the roads around here that well.
I'm willing to help organize a get-together (drive-together?) if I can get some guidance on a route.
East of the River huh? I live southeast of Hartford now.
IMO, the following guidelines should be followed when planning one of these drives:
1. Pick a destination. Usually an interesting place to stop and have lunch and chat.
2. Find a route that has as many sharp turns and as few stops as possible. Even if this means criss-crossing a more direct route on your way toward the destination. No one minds since the idea is to have a fun drive rather than finding the quickest way to the destination.
3. Avoid populated areas as much as possible.
From Litchfield, one could go West toward Lake Waramaug and Hopkins Vinyard. I might even go Morris, Lakeside, Washington Depot, and then New Preston. Another option would be to go Northwest towards Cornwall, and then turn Southwest, stopping in Kent for lunch (I always liked the Bulls Bridge Inn).
Part of the fun will be getting into your spider and experimenting with different routes
If you organize a drive and give enough notice, I'll definitely be there.