25 miles should get me out to Bedford, Pound Ridge, Lewisboro, etc on the East. It should get me out to around the Hudson River on the West without any problems. North to somewhere in mid Putnam County. South to somewhere around Ossining / Chappaqua.
North, I don't mind going farther, because I am always going against traffic going there and coming back, plus fuel up there is cheap. South, I don't like because the fuel gets more expensive, and then traffic becomes an issue, as well as where to dump chips and wood. East, big $$$ so I don't mind. West, I'm not big on scuba tree work just yet, so the Hudson is just fine for me. I did go once last year and looked at a job to the NW of here. Gave it to another ArboristSite member because it took over an hour to get there.