Up around Bradley Airport there are lots of nice back roads and State routes. Try Rte 20 west, ride around Lake Barkhamstead, at the top of the lake, coming back down it, change to Rte 181, that will hook up with Rte 44, head back east to go back towards Windsor.
Another idea is head across the CT river and ride any number of State roads towards Staford raceway. I don't usually ride up in that area, but have been, 'passin' through a number of times.
The Rte 44 and upper Rte 8 are very scenic roads made for bikes. 44w to NY22 north to 23 E to 7N to 23E to 8S back to 44 is a great loop for a day trip. Up in Great Barrington MA there are plenty of good biker friendly eateries.
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