I’m lucky to have a year-round early morning reverse commute from Kenmore Square in downtown Boston out to the southwest suburb of Norwood, and then I take a commuter train back to Boston with my bike. I have four major outbound routes, each defined by the hill I climb, and the local environment. Each route is about 14 miles long and though different, they are encompassed within a distance of less than about 2.5 miles from the farthest east to west. All of them are mostly residential to light commercial thoroughfares. In increasing order of the difficulty of the hills, I describe them as:

-“gritty” urban (Centre and Washington St through Jamaica Plain and Roslindale)

-pleasant suburban (Pond St to Goddard St and on to Newton St and Independence to the VFW Parkway through West Roxbury)

-pleasant urban (Jamaicaway and Centre St to Rte 1 through Jamaica Plain and West Roxbury)

-ritzy suburban (Walnut St to Warren to Lee and on to Newton St through Brookline).

These are not especially tough hills, but noticeably different in effort. My favorite route is the pleasant urban one, and it is also the best maintained during the winter. The last four miles of each of the routes is a final common pathway through Dedham to Norwood.

When I go into training for a century according to a ten-week schedule I follow, my weekday mileage increases gradually from 14 to about 30 miles and I expand my routes, going through some of the most desirable cycling areas in the Metro Boston area such as Milton, Newton and Dover.