Discussion: Why not

canal trail to Putnam-Newhall-Mill Rock-Prospect?
or, if you don't like the Prospect hill, take Armory to Edgehill / St Ronan to Edwards
or Armory to Edgehill to Cliff across Whitney to Nash to East Rock to Livingston to some cross street to Orange
or forget the canal trail and go from your place across Whitney to Ridge Rd, then up Farnam Dr and down through the park to Orange.

I really don't think the bike trail through Newhallville is safe.

The first option is kind of what I do, but I stick on Leeder Hill instead of going out to the Canal Trail. That bit of the ride is totally fine. I like the Ridge Road idea too. Prospect is awful for potholes and general mess on the flatter bits - they've resurfaced both ends but not the middle.

I think part of it is the road bike - trying to handle potholes and maniac drivers is no fun. Might have to switch back to slow but reliable mountain bike then I only have to worry about one of them.

Good to hear your opinion of the trail - I've heard so many wildly varying ones, but I certainly agree with you from my brief experiment on Thursday.