Maine has a short summer tourism season and the further north you get, the quicker it ends, with early peak foliage and shorter days. It's almost too late, but not quite, to enjoy the foliage in northern parts of Maine. I'm going to recommend a trip itinerary off the beaten path to the Blue Hill Peninsula and Deer Isle and Stonington.
If you can't find a room with Vacation Rental By Owner, or aren't pulling one behind you...I can recommend an itinerary that includes a few places to stay and eat that don't put up shutters after Labor Day!
Start at the Farmhouse Inn in Blue Hill. You won't need to leave the property to have what locals consider one of the best meals in the area! While the little village of Blue Hill is very sleepy in the fall and winter, the Blue Hill Heritage Trust maintains several trails up Blue Hill, a moderate hike up about 1000 feet with spectacular panoramic views from MDI to Bucksport that will keep you busy in any season and work up an appetite.
Blue Hill Bay from Blue Hill Mountain, trails maintained by Blue Hill Heritage Trust, who manage dozens of trails and walks through out the area. Including much easier ones through blueberry barrens or along the shores of the ocean.
An option for another day in Blue Hill is the Barncastle. This inn also features a full service restaurant and bar that is renown for their wood fired pizza. From here take a ride (in your car or on your bike, but beware, cycling here is not for the faint of heart, with little shoulder, big trucks and even bigger hills) follow route 15 to Route 175 towards Sedgwick and Brooklin. Enjoy incredible views and a description of the area on interpretive granite markers at Caterpillar Hill.
Views from the overlook at Caterpillar Hill in Sedgwick to the Deer Isle Bridge and Deer Isle
Ride down the dirt road in front of the dramatic Caterpillar Hill overlook and find the public beach and boat launch on Walker Pond. There are more trails here for hiking and there are picnic tables by the water if you'd like to pack a picnic. If you want to get out in a kayak or canoe on the lake to search for loons before they relocate to the ocean for the winter, try contacting the Activity Shop before you leave Blue Hill...they can even arrange to meet you and deliver bikes or boats right where you need them.
The colorful shores of Walkers Pond
After ohh-ing and ahh-ing over the foliage and possible working up an appetite kayaking or biking, a stop at LL Frijoles in Sargeantville on Route 15 will fill you up with locally sourced produce and seafood to create yummy Mexican food with a Maine accent! Make a full loop back to Blue Hill, with views across Blue Hill Bay to Acadia National Park in Brooklin or head down Route 15 to Deer Isle and Stonington for a stay there.
In Stonington, stay at Boyces Motel an affordable, simple motel style inn that is immaculately clean and perfectly located in "downtown" Stonington. Innkeeper Barrett Grey is what makes me call it an "inn", providing incredible hospitality and everything you need for a comfy stay. The motel is located right on Main St, and although some rooms are close to the sleepy main road in town, you are close enough to the harbor across the street to hear the fishermen heading out to their lobster boats, and not much else!
Stonington, and the Opera House Arts, historic Opera House on the hill.
Be sure to explore Route 15 from Sunshine to Sunset (actual places!) and don't be afraid to drive down every spur road, because on an island, you cannot lost; just turn around and head back the same way you came! For dinner, rely on Barrett's recommendations, he's always in the know about what's good right now! or have him set you up to make your own steamed lobster dinner in one of his apartments with views over the harbor. After dinner, check out what is on at Opera House Arts, which provides year round programming of alt movies and other community and professional productions within walking distance of Boyces.
Every road leads to another scenic spot in Stonington, and ends at the water, making it almost impossible to get lost!
If you are looking for beautiful foliage without the crowds and traffic, head "downeast" to Blue Hill and Deer Isle where you will find that the lights are on, and the hospitality is as warm as the blazing wood stoves!
(Be sure to check the linked websites for open hours, most places are open on limited days in the fall and winter!)