BITD when I first started getting serious about cycling, I was involved with an organization that ran summer bike trips. Back then we were based in 8th Street in Manhattan, and many trips left the city by trains out of Penn or Grand Central Stations.
We ferried bikes up there riding our own, and pulling the other by holding the stem so we could steer. It took a bit of practice to learn, but it really wasn't difficult, even in NYC's congested stop and go traffic.
This trips were only a few miles, so I don't know how it would play out on a longer ride. However, if there are no hard hills, you might borrow a bike and practice in an empty parking lot, and see it it can work for you.
BTW - the method is still used by many of NYC's more skilled bike thieves.
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WARNING, I'm from New York. Thin skinned people should maintain safe distance.