Portland may be Maine’s largest city, but it doesn’t even break the top 300 in the United States. This speaks to the quaintness of Maine’s most populated hub. But take one look inside the classic merchant houses and repurposed doors made of ship parts, and you’ll find that Portland is no slouch on culture. Stroll down Congress Street, where one chichi art gallery leads to a refined artist’s studio and then on to an offbeat café where the only thing that isn’t fresh is the compost out back. Summertime sees an influx of tourists, but autumn boosts the city’s sophisticated whimsy into overdrive. For a dose of fall, cruise the coast and climb through the mountains, where orchards are ripe for apple picking. You’ll find prime leaf-peeping where Maine’s legend started—complete with gorgeous lighthouses, roadside farmer’s markets, and a crisp New England chill.