I've sailed and motor boated all over the Norwalk Islands and also on Lake George. Congrats on your boat. We always loved to have a small soft sided cooler with a strap, the kind with extra pockets on the outside and vinyl covering. You can really load those things up with everything from sunscreen to flares to sandwiches or beer.
I'm a bit more concerned about the Norwalk part of you plan. Its protected but I would still get the dog a life preserver - at least if you tip over he will float. Don't go to close to any major navigational buoys - they attract big traffic - and you are in traffic in Norwalk a lot. I remember some really big fast yachts passing right by my boat and throwing an 8 foot wake at us - no exaggeration either.