Where to stay:
History buffs should opt for the Inn at St. John, located in a three-story Victorian guesthouse that opened in 1897. King-size rooms with private baths run from $99 to $215.
What to do:
Head to Wolfe’s Neck Woods State Park ($6 admission) in Freeport, 30 minutes from downtown Portland, for the impressive foliage and a free ranger-led tour to visit resident ospreys along Casco Bay, suggests Bob Witkowski, author of 100 Things to Do in Portland, Maine Before You Die. For a different perspective, take a half-day guided kayak tour with Portland Paddle ($65).
After working up an appetite, head out “on the P” (the peninsula), as locals call it, to dine at one of the city’s 300 restaurants—not bad for a metropolis with a population of 65,000. Pamela Laskey, owner of Maine Foodie Tours (from $49), suggests Boda for its Thai tapas, such as quail eggs seasoned with soy sauce and scallions ($3 to $10). And don’t leave this storied maritime state without visiting a lighthouse. Sept. 10 is Maine Open Lighthouse Day, which means you can take free tours of dozens of lighthouses along the Maine coast that are rarely open to the public. In Portland, don’t miss a trip to the stunning Portland Head Light, where the first oil-lamp sentry was lit in 1791.