1. Island Inn
City: Monhegan Island, ME
Category: Accommodations
Telephone: (207) 596-0371
Description: An impressive shingle-style castle of a place, this gray beauty dates back to 1816, or at least part of it does. It sits on a rise lording over Monhegan Harbor and Manana Island, and it has two types of accommodations inside. There are 34 rooms and suites, some of which share baths, and the sunlit-rooms have nice painted floors, cushy wicker chairs, and down comforters for those cool September evenings. The inn’s dining room is arguably the island’s best, and its wraparound porches and Adirondack chairs are fine places to while away a day.
2. Monhegan House
City: Monhegan Island, ME
Category: Accommodations
Telephone: (207) 594-7983
Description: Monhegan has a handful of places to overnight, and they all have different things to recommend them. The Monhegan House is just plain classic, the oldest continuously operated place on the island, dating back to the 1870s and with 28 rooms on its four floors. Everything about the boxy old inn is comfortable, from the long porch out front, topped with rockers, to the spare, quiet, breezy rooms. The floors creak underfoot, the bedspreads are the white nubby ones your grandmother used to use, and there are big leather chairs near the fieldstone fireplace in the lobby for lounging. Some people are bothered by the fact that bathrooms are shared—all of the showers and toilets are grouped together on the second floor—but it is very clean and almost has a summer camp vibe, making it a fun adventure. Right near the center of the village, the porch has traditionally been a center of activity on the island, so spend any time on it and you’ll quickly feel tuned in to local goings-on. Rates include breakfast. Open from mid-May to mid-October.
3. Trailing Yew
City: Monhegan Island, ME
Category: Accommodations
Telephone: (207) 596-6194
Address: Lobster Cove Rd.
Description: If you had an eccentric grandmother with an island cottage, it might feel a bit like the nifty Trailing Yew. The simplest and least formal of all of the island’s lodging options, the place is actually a compound of four weathered cottages clustered around a hilly courtyard. There are 35 rooms to choose from, and electricity is scarce—just turn on the kerosene lamp. Baths are shared, and only some have electricity. Dining here is an experience, with meals served family style so that you’re literally rubbing elbows with strangers. But everyone is having such a good time, it’s a pleasure. Not fancy, this place, but fun. Don’t forget your flashlight.
4. Monhegan Light
City: Monhegan Island, ME
Category: Tours & Attractions
Telephone: (207) 596-7003
Address: Lighthouse Hill
Description: There are many reasons to plan a visit to Monhegan Island, 10 miles off the Midcoast, and one of them is this 47-foot tower. A dull gray granite, it isn’t the most impressive of the state’s beacons, but its location most certainly is. The light is set high atop a hill where the island meets the sky, and it lords over both Monhegan and Manana Island, its uninhabited sister isle across Monhegan Harbor. The place is so grand you could sit on the lawn here for the better part of a day and never get tired of it. If you visit only one lighthouse in Maine, make it this one. The light was automated in the late 1950s, and the grounds and buildings surrounding the tower were sold to the local island association. Today there is a very fine museum in the keeper’s house that documents the natural and cultural history of the island. It includes exhibits that explore the fishing industry and early island life, and it features works by some of the nation’s most famous artists, many of whom—George Bellows, Rockwell Kent, Jamie Wyeth—came here to live and paint. In recent years some of the collection was moved to the renovated and climate-controlled assistant keeper’s house, making the museum twice as impressive. It’s open daily from 11:30 a.m. to 3:30 p.m. from July through September. Admission is free, but a donation is encouraged.