Connecticut with a newbie?

I'm looking for a two day hike route. I'm taking a buddy for his first time, and I need a suggestion. I want something convenient from the Bridgeport area. I would like something moderate, under 20 miles, nice ridge views, good water and campsite, safe parking, preferably a loop (we'll have one car) but out and back is acceptable. He's fit and game, but I want to go relatively easy on his first trip. I'm mostly concerned with making it enjoyable. Good scenery & wildlife, maybe a waterfall, peaceful company OK, but no crowded "party" areas (we're over 40 folks).
I may need to meet him coming from NYC. Is there anywhere accessible by train/bus besides Pawling? This does not necessarily need to be on the A/T. Fires and dogs allowed is highly preferred.
Where would you take a newbie in Ct?