Greenville

"Maine is home to vast stretches of breathtaking coastline, which this time of year is where all your Coastal Grandma dreams can come true. If it’s a good meal, a brisk walk by the ocean and a sunset glass of Chardonnay followed by an early bedtime you’re after, the sleepy, seaside towns like Kennebunkport are where it’s at. You’ll get a taste of foliage by the coast, but true immersionin the Pine Tree State's wild crimson, pumpkin, and amber-hued woods, however, requires heading deeper inland. For superlative fall foliage, go hiking in northern Maine in early October. Explore Baxter State Park and the forests to itsthe southwest, the contiguous Nahmakanta Public Reserved Land and Appalachian Mountain Club 100-Mile Wilderness Conservation Area. There are enough hiking trails to keep all skill levels happy, and regardless of which you choose you'll find paths lined with deciduous trees and towering evergreens, and punctuated by boulder-strewn streams, lakes, and ponds. (Bonus: This is prime moose-spotting territory.) Where to stay and eat Kennebunkport in the summer? Idyllic, albeit a bit crowded. Kennebunkport in the fall? Cozy seaside heaven, with just a fraction of the visitors. Many of the town’s best hotels start closing for the season at this time of year, but the Cape Arundel Inn & Resort remains open year-round. The location offers the best of both worlds: a quick walk or bike ride into town, but a secluded location directly on posh Ocean Avenue so you can fall asleep to the serene music of gently ebbing waves. And come nightfall, its restaurant Ocean offers sweeping views of the water from a dining room illuminated by votive candlelight, and a tasting menu with wine pairings that’s one of the better fine dining experiences you can have in Maine. Book a room in the main house so you can gently Coastal Grandma your way upstairs to bed after dinner. Camp out at this rustic yet comfortable Appalachian Mountain Club–backed Medawisla Lodge and Cabins in Greenville, Maine. Accommodations include hilltop cabins with private baths, cabins with shared bath, and a main lodge, where you can also pick your level of frills. The luxury here is the location: Smack in the center of wild Maine, you have immediate access to fly fishing, hiking, biking, kayaking, and paddling, all with surreal autumnal backdrops. Opt for a meal package at Medawisla, which includes a fresh-cooked breakfast and dinner, plus packed trail lunch daily. And just keep in mind that they close for the season this year on October 15th, so it’s better to book sooner than later." - Todd Plummer, Paul Rubio