I do a reverse commute from Kenmore Square in Downtown Boston to a suburban destination. I have four distinct routes on my usual commute, each about 14 miles long. I describe them as "gritty urban (but interesting and safe), "pleasant urban, "pleasant suburban, and "ritzy suburban." When I'm in training during the nice months I can expand my routes to include idyllic cycling regions (Dover-Sherborn or the Blue Hills of Canton for example).

BTW, I take my bike home to Boston on a Commuter Rail, with the station about two miles from home. Even on that short hop, I have four different routes.