Cumberland

Cumberland is where Portland keeps its school districts and its lawns. A first date here is a structural mistake unless one of you already lives on the cul-de-sac, in which case it is a confession. There is no main street to walk, no bar to drift to, no plausible reason to be on Tuttle Road after dark. Twin Brook Recreation Area is the one honest move, daylight only, dog optional. The tradeoff is privacy at the cost of plot. Drive ten minutes to Falmouth for dinner, or fifteen to Portland for a personality. Cumberland is for the second date, or the seventh.