In the villages and along the back roads you can find wonderful bed-and-breakfasts run by innkeepers eager to share Way Down East's laid-back charms. Some are cozy places where you might feel you're staying in a friend's country house, while others are grand mansions where the rooms are filled with antiques. Hardly any have air conditioning—with cooling sea breezes you don't need it. Don't write off anything called a cottage; many in this region are lovely. Inns often charge less than you might think; upscale establishments that would command $150 a night or more in Bar Harbor often have rooms for about $100 here. What you won't find Way Down East are chain hotels, though there are some inexpensive roadside motels, most of them in larger towns.
Hike Cutler's Bold Coast: The open ocean views are stupendous, but what also makes hiking here so memorable is peering down at coves below the cliffs, or at wild cranberries between the rocks at your feet.
Meet the innkeepers: Some offer rooms with shared baths without apology, others pride themselves on private baths with spa tubs, but all share a passion for the area and will give you pamphlets galore.
Savor chocolate at the end of the road: Way up the Maine Coast in Lubec there are not one but two scrumptious chocolatiers. Continue on to Calais, where it's a short walk across the bridge downtown to the Chocolate Museum in St. Stephen, New Brunswick.
Explore Campobello Island: Roosevelt Campobello International Park is a must-see, but there are other gems on this Canadian island, like the wide sand beach at Herring Cove and the village of Wilson's Beach, where the water views are like unfurling ribbons en route to East Quoddy Head Lighthouse.
Mingle with artisans: Artists selling fine paintings and crafters offering less-pricey wares all have stories to tell, about themselves and the region and why they are here.