I have not read the entire thread but I offer this recommendation: check out the CT Forest and Park Association's two volume Blue Trail guide:
Connecticut Walk Book | Connecticut Forest & Park Association
The Connecticut Walk Books, in two volumes covers the state's Blue Trails East and West of the CT River. It's a great resource and available for purchase (pricey, I own one...) or you can [I]borrow it from your local library![I]
CT has many family friendly trails! GL
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