Reddit reviews AMC's Best Day Hikes in Connecticut: Four-Season Guide to 50 of the Best Trails from the Highlands to the Coastal Lowlands
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Authors: Rene Laubach and Charles W.G. SmithISBN: 9781934028100
I would strongly recommend picking up AMC's Best Day Hikes in Connecticut. Really gives you a good overview of the hiking spots, as well as a ton of background information about the parks and suggested routes.
Up in far northwest CT, you can actually hike up to the Appalachian Trail from Salisbury, CT. I believe it's the Lion's Head Trail. From there you could go pretty far either way.
One of the bigger areas I've seen is in Guilford, on the coast: Westwood has some pretty long trails if I remember correctly. I've done one that's only a couple hours but there were definitely options to extend that further.