Where to take a newbie in Connecticut?

[Dirty Nails]

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?

[Tinker]

The northernmost section, from Rte 41 in Conn. to Jug End Road in Ma. is probably the most scenic section of Conn. The climb up Lion's Head from Ct. 41 (heading north) is pretty steep, plus you have Bear Mountain, Mt. Riga (if I remember correctly) and one more good climb before descending Jug End (very steep) where you can walk back (to the right - east) to Rte. 41 and hitch south back to your car. Don't plan on using the Plateau Campsite. It is a trashed out, sloping, muddy party spot a hundred yards from the parking spot on Ma. 41. All the other shelters and campsites are pretty nice with the Hemlocks shelter and the nearby campsites among the best. There's one shelter a couple of miles north of Lion's Head (probably Riga shelter) with a beautiful view east to catch a sunrise in the right conditions. I don't have the distances right in front of me, so I can't be much more help.

Btw: Sages Ravine, right on the Ma/Conn. border is absolutely stunning, and has tent platforms right along the stream (though a safe distance from it, of course).

[Tinker]

This might help a bit: http://www.atdist.com/

[Driver8]

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 agree with the Salisbury/Sheffield recommendation. Start at the Bunker Hill Lion's Head trailhead, or at the Rt. 41 Salisbury one for the A.T. Any of the campsites is in great condition. For a newbie, stopping at Sages Ravine might make for a good one-day destination - just mind that the descent of the north side of Bear Mountain is a quite steep and treacherous 0.2 miles at its core. I highly recommend a visit to the side trail between Mts. Race and Everett in Mass, the Race Brook Falls Trail. Maybe on day 2, hike from Sages or Laurel campsite, over Mt. Race (the views from the cliffs are awesome), then, if your legs are game for it, ascend Mt. Everett, which is beautiful, crowned, like Race and Bear, with a unique old-growth scrub forest and offers great views, then descend back to RBF trail, taking it down to Rt. 41, from which you can hitch a ride to your car. If you go down RBF trail, descending along the south (right) bank of the brook after you cross it below the 80-foot high big upper falls will allow you to take in five of the six falls. A bit slippery in places, but a beautiful adventure.