Hey @Dave_O1 .
I’m not sure if you’ve seen the resources Megathread but there are a few tools which may be of use to you: Link to Zwift Resources - Megathread #2 🗺
I’m specifically thinking of ZwiftMap.com and Zenturizer, which can be used to search for and examine routes. I’m rather fond of the former on account of the graphical nature - you can “scrub” through the route (desktop and tablet friendly) to see what different segments look like.
If you’re running Zwift on a PC, there’s also the RoadCaptain add-on which would let you “auto-pilot” through a route of your choice.
EDIT - while you’re at it, check this thread: What is the worst Zwift World, and why is it New York? - #65 by Paul_Rayner (tongue-in-cheek title - read on)
I wasn’t sold on NYC but several users pointed out some really good looping routes around the perimeter with the type of rolling stretches you find in Watopia’s “The Esses”. @Anna_Ronkainen had this to say: