Originally Posted by
Lenbrazil
I grew up in the city, spent several years of my adult life there and have visited repeatedly since moving to Brazil. My focus will be on seeing friends and family and taking care of some matters that need to be dealt with. But I should have time to ride especially when my sister is otherwise engaged. Plus I'll get to see places I've never gone before or haven't been in years or even decades.
You don't have to explain yourself. There are plenty of options here, both within the city and in the surrounding burbs. It's mostly a question of time, weather, and ambition.
Part of the problem is that most of the nicer riding is at some distance from the city, so unless you're considering rides of 75+ miles, a decent portion will be in the close in burbs, which I consider dead air riding, for a bit of nicer riding at the far end of the loop. If you are willing to do a longer ride, look at a map and consider a ride out to Greenwood Lake. Probably the 1st and last 15 miles from the GW will be suburban street riding, but it's kind of OK for what it is, but west and north from Pompton Plains it's nice and open, and you have a number of options to make a loop of your preferred length.
Probably the closest open road will be the Alpine ride described earlier, which can be extended all the way to Nyack or beyond depending on your ambition. Otherwise, I'd "zone skip" using Metro North so you can spend most of the ride on the nicer, more open hillier roads I described earlier.