Chebeague Island Inn | Late Fall Maine Getaway

It was just pushing just past eight at night when the ferry’s main light came into focus amid the nighttime’s inky blackness. “There it is,” I said to my wife, pointing in the direction of the round orange beacon. “There’s our ride.” Some four hours earlier, we had left our home in southern New Hampshire, navigated the traffic around Portsmouth, and filled up on big sandwiches at Duckfat in Portland, before completing the last leg of the journey to the water. Ten minutes after our first glimpse of the ferry, my wife and I excitedly stepped on board for the trip across Casco Bay for our weekend jaunt to the Chebeague Island Inn.

We were one of the few. It was the first weekend of October and also the final weekend of the season for the hotel, nearly five months exactly since it first opened for the summer in mid-May. The goodbyes had already started. A number of its full-time staff had left the island for winter work in Portland. Others had left the state (and the coming winter) completely for seasonal jobs in Florida. The atmosphere at the inn was giddy, a mixture of excitement over wrapping up another summer and anticipation of the start of a new one. During our Sunday breakfast, I heard the kitchen team lament the making of their final batch of pancakes of the year. “Our last ones,” someone said, with a laugh. “It’s so sad.”

There were goodbyes across the island, too. During the summer, the population swells to close to 2,000 people. By late autumn it drops to around 350. A quiet tone certainly enveloped the island by the time of our visit. The weather had an easy, warm feel to it, but there seemed a ready embrace for what was to come. Wood was stacked, lobster traps tucked away, there was talk of talk of the coming season. Would it be another cold winter? How much snow could we expect?

Island getaways can be ideal escapes. That’s because they require effort. There’s the car, then a bus ride, followed by a boat, then a shuttle. It’s not simply a matter of putting in a few hours on the interstate. It’s an investment of time. But that investment yields some real rewards. I didn’t think about the window I needed to trim out at my house, or the story I needed to finish writing. I felt the way a good vacation is supposed to make you feel, like I truly was away.

The Inn certainly had something to do with it. Chebeague has an easy feel to it. A familiarity, even if you’ve never stayed there. The great room became an easy place to hang out for an evening glass of wine, or to sit back during the day and catch up on some reading. The porch was another favorite spot, with long views of the water and the promise of one of the finest sunsets in all of New England. We took it all in during our stay and then on Saturday night headed back to the mainland and into Portland for a memorable dinner at the Inn’s recently opened sister restaurant, Evo. There, we savored the chef’s tasting menu, a full Mediterranean excursion of seafoods and wines, followed by a first: baklava ice cream. Then it was back to the island and the Inn for the night. We were, you could say, following a tradition that began in the late 19th century when the hotel first opened. Then known as the Hillcrest Hotel on Chebeague Island, the original building burned down at the start of the 20th century and was rebuilt in its current form in 1924. In 2004, the Inn underwent a massive renovation.

Much of the charm of the Chebeague is that it’s a part of island life. Monday night dinners are a regular event for island residents during the summer. During our visit, neighbors streamed in and, on Sunday night, the final night of the season for the big place, Food and Beverage Manager, Matthew Kurt, Executive Chef, Joel Frahm, and Front Desk Manager, Tina Lewis, welcomed a full house to the dining room for one final meal. “Join us Sunday to drain the keg!” a handwritten sign advertised. One of the memorable faces of the Inn is Ricki McDonald, an island native who returned to Chebeague in 2011, after spending many years in Boston. Her first job had been in the kitchen when she was thirteen and the Inn was owned by the parents of one of her friends. Now she was back.

She has many stories about the Inn. One of my favorites involves the search for the coveted silver dollar in the Inn’s large stone chimney. As legend has it, a stonemason had hidden a coin in the stone in 1924, and whoever found it was promised a lifetime of health and happiness. Ricki said she had spent hours over the years looking for the dollar. She and another colleague had even gone so far as to use a metal detector to locate the thing. They still came up empty. “I’m beginning to wonder if it’s actually there,” she told me. Just before we left on Sunday morning, I took my own stab at finding the coin. I scoured the outside of the chimney, where it was supposedly located. Like Ricki, I came up empty. But maybe I didn’t need it. After an early October weekend tucked away on quiet Chebeague Island, I felt the kind ofrejuvenation that I think the mystery coin promised. Chebeague Island Inn. 61 S Road, Chebeague Island. 207-846-5155; chebeagueislandinn.com