by Joe Wallace

Like the pic? It’s from a Cleveland night spot adjacent to the hotel I stayed in on the first leg of my current 12-day road trip from Chicago to NYC. I’m blogging at Turntabling.net about indie record stores between the two points, and making copious notes of my experiences to share with you here.

A prolonged stretch of travel writing has its own challenges. When I did this last year from Chicago to San Antonio, Texas, I didn’t really know what to expect, but I had the luxury of not worrying about servicing freelance clients while on the road. This time I decided to add that challenge to the mix and see what happens.

My plan was to use the new free-for-all wi-fi service at Starbucks, since the coffee chain seems to be everywhere. I figured at the very very least I might have to drive or walk to the nearest coffee shop to get connectivity and post away.

That strategy worked for a while. In Cleveland, which is quite possibly one of THE most freelancer-friendly cities in the U.S. it was child’s play to get a connection and file my work for my clients. Ditto for Pittsburgh, which had plenty of free wi-fi to go around.

Not so much once I got closer to the East Coast. In Allentown I had trouble connecting to the hotel’s TWO wi-fi servers, and when I hit Newark, I learned that not only does Starbucks seem to be quite scarce here (at least in the vicinity where I am staying near Penn Station) but there’s no Panera Bread, either. And the hotel I’m in is quite happy to charge me to connect in addition to the room fee.

I bit the bullet and paid the extra usury for wireless Internet in order to keep current with my clients, but I have to say, it’s a bad idea to depend on that free wi-fi service on a road trip unless you’ve done your homework first–what I should have done was check each city on my itinerary via Yelp.com or some other restaurant reviewer site to see if I’d be able to depend on the free stuff for the entire trip. I’d have saved myself some extra hotel charges and a lot of headaches trying to find an office-away-from-the-office. It was via Yelp that I learned that Newark is short on the free wi-fi near where I’m staying, and via Yelp that I found plenty of places in Greenwich Village to connect instead. A 2o minute train ride into NYC was the cure for many of my problems…

In my next report, a list of the freelancer-friendly places I’ve been so far.