What'saCobra:
While your listed as Miami, appears you spent time in VT. I was in the Stratton/Bondville/Jamaica area for over 20 years.
Totally agree, Route 100 north from Route 30 is a great ride. We used to go North west , take the 2 or 3 car ferry over to Fort Ticonderoga, then head back South on the New York side. Many nice conversations and coffe breaks in the General Stores
Two other great rides are in the Northwest ( Lime Rock Race Park ) and NorthEast corners of CT, then head down state.
Also enjoyed the Route 30 ride from Brattleboro and then heading to Manchester, especially before Route 30 was widened
A favorite stop is at the Vanilla Bean Cafe in Pomfret CT
http://www.thevanillabeancafe.com/