There’s actually no bad time to escape to Chebeague, one of Maine’s loveliest islands, but locals know that September is the island’s peak time. The summer crowds go away, and the foliage is already beginning to peek through. The crisper evenings demand bonfires and s’mores, and best of all, the water is downright temperate -- the warmest it will be all year.
Where to stay: Chebeague Island Inn (open through October 15th) is the only game in town; good thing this grand hotel is one of the loveliest places you’ll stay in your lifetime. Simply appointed rooms, a grand fireplace in the main room with board games aplenty, a wraparound porch facing the sunset, nary a TV to be found... you’re forced to do that relaxing thing.
What to do: Bike the circumference of the island -- the inn lets you borrow bikes for free -- and wave at everyone you pass, because they’ll wave at you. Grab lunch at the Ebb & Thyme Bakery & Cafe, and make sure you walk over to Little Chebeague island when the tide is out. Take a late-afternoon dip at Hamilton Beach when the tide comes back in (the inn will set up chairs for you). Savor the surf and turf at the inn’s award-winning restaurant, which sources many ingredients from the island’s only farm.