3 Day Trip

My brother and I are planning on a mid- to late August 3 day kayak trip. We both live in Connecticut, and would like to find a good trip that, including driving time, will give us 3 days. Obviously we want to be paddling more than driving, so it needs to be within probably a three hour drive. We’ll need to camp, so we need to find tent-friendly areas. Finally, one last challenge: we’d like to possibly get to some town or something on the second night to have dinner in town, but if that sacrifices beautiful areas, I for one am more intent on being in the wilderness itself.

I know that’s all a lot to ask for, but if anyone could help me it would be greatly appreciated. Thanks.

A couple of suggestions
Block Island. I paddled from Pt Judith and back a few years back on a day trip. You could circumnavigate the island. The Hudson River, The Connecticut River. Aren’t there some islands off the CT coast you could cross to?

Lake Champlain…