By the second week of October the maples on Wallens Hill go the color of struck matches, and every leaf they drop lands on somebody's grass. Dylan's Lawn & Tree Services spends those weeks raking, blowing and hauling — off the lawn, out of the beds, clear of the walks — after a summer of weekly mowing and trimmed edges. Once the color is gone and the ground sets hard, the plow goes on the truck, and Winchester driveways get opened through the night while walks are shoveled and slick spots sanded. This is a town that hands you a different job every few months if you're paying attention. The reward is plain: bare pavement by breakfast in winter, and in July a lawn that looks cut on purpose.