PORTRAIT OF PLACE – July 2014
By Sophie Nelson | Photography Nicole Wolf

The modest charms of an island off of Boothbay Harbor

Boothbay Harbor is a dream. One with small white houses and bright shutters and picket fences lined with daffodils. It is a place where, on the right day, the grass looks extra-green, the American flags especially patriotic, flapping wildly about in gusts of ocean air. In this part of the southern midcoast the water seems a little more inviting, calm in the embrace of peninsulas, striped with piers and spotted with islands and boats. The roads stick tight to the ruffled shore, so it is almost difficult to avoid water views on a ride around town. The other day, I followed such a road to Southport, an island off of Boothbay Harbor, sticking its neck out into Sheepscot Bay. If Boothbay Harbor is a dream, Southport is its long, quiet conclusion. Also charming in the extreme, there are more trees here, and the small white houses are hidden like secrets among them.

It isn’t really fair, I know, to call this very real place a dream. People live here, have been living here for centuries, and many know long winters and hard work all too well. There are crooked cemeteries to prove it, and low-slung Capes that have sheltered generations. There is a school—a long white building with a duck pond out front—that serves Southport students through sixth grade (in seventh, they go to Boothbay Harbor), and a war monument at the center of a three-way near that school and the Southport General Store.

Evelyn Sherman, a trustee at the Hendricks Hill Museum and the descendent of the fishermen who settled Cozy Harbor in the late 1700s, tells me most people fish for lobster these days, and I see proof in the trap-filled boats docked in Deckers and Christmas Coves. Other year-round residents (there are about 600 in total) find work in the service industry, as plumbers, electricians, and caretakers. In the summer, Southport comes to life—restaurants like Oliver’s reopen, hotels like the Newagen Seaside Inn and the Ship Ahoy Motel—but for much of the year, the Southport General Store is one of the only businesses in operation on the island.

On the morning of my recent visit, outside of the General Store, I nod hello to a man in a truck who is eating breakfast, listening to the radio with the windows open. Inside, the special of the day is written on a chalkboard behind the counter—a pot roast sandwich with sautéed onions and homemade sauerkraut—and although it is hardly past 11 o’clock I am tempted to order one, to take a seat at one of the two-tops in the back among cracker boxes and cleaning supplies. I don’t quite have the hunger or the time, but it seems like that pot roast sandwich special might deliver just the salty dose of reality I need after crossing the wiggly bridge into Southport and beholding that achingly adorable view of houses perched on steep slopes overlooking Deckers Cove and the awnings of the lobster pound and Robinson’s Wharf, the roads winding down the island.

This time, I forgo the sandwich to explore the loop of roads around Hendricks Head Preserve and the beach there—a narrow beach, wide at low tide and quiet at the cusp of summer. Kids in sun hats chase gulls and build castles in the soft sand. In the distance, perched at the end of a grassy, rock-rimmed outcrop, I admire the red rooftops of the Hendricks Head Lighthouse and its neighboring houses—a rambling saltbox and a tall, narrow home cut out of the sky in steep angles. Despite the epic location, the homes, like most I encounter on Southport Island, are fairly modest.

In fact, many Southport homes are merely hinted at by address placards at the foot of wooded dirt driveways, or so shrouded in spruce it can be difficult to make out their shape or color. This is clearly a place for people who appreciate Maine’s forests as well as its water. In parts of Southport, I might even go so far as to say the island has a lake-like feel. There are basic camps painted in browns or dark greens with deep screen porches, and larger-scale camps landscaped to fit seamlessly into their surroundings. There are colonials as well as modern homes tucked among the trees.

Steve Malcom of the Knickerbocker Group, who has renovated and built a number of homes on the island, from very basic cottages to elaborate homes overlooking the water, tells me it’s the “live and let live,” “fuss-free” atmosphere of Southport, in addition to the raw, woodsy beauty, that attracts people. It’s possible to become a part of the community on one’s own terms. Social life isn’t very glittery; it often revolves around the library, or volunteer opportunities with the local fire department. Nightlife is a conversation and cocktails on the porch, a family dinner at Oliver’s, or a trip in to Boothbay Harbor.

Part of the intrigue of Southport, and no doubt part of its appeal for year-round and summer residents alike, is the possibility of privacy. Instead of hugging the coast, as they do in Boothbay Harbor, the main roads on the island are set slightly inland, with residential roads snaking off of them to the water.

Having so many homes hidden from view contributes to the rural feel of Southport, and, since the ocean is invisible for much of the drive along the east side of the island, arriving at Cape Harbor becomes that much more special. The view opens up as fruit and flowering trees replace towering pines, and camps are traded for classic summer cottages, breezy and pale in color, with rose-entwined lattice-work, perched on the grassy slope down to the water. This area has seen an influx of summer visitors since the late nineteenth century, and since the 1940s, many of those vacationers made Southport their year-round home upon retirement, winterizing old family cottages or building new houses to meet modern needs. One intriguing property, set on a slope overlooking the water, is comprised of two almost identical cottages outfitted in a weather-beaten siding. The signs on the houses that read 1906 and 1996.

The Newagen Island Inn, at the tip of the island, is a Southport summer institution. The roads surrounding it are some of my favorites on the island. Here, glimpses of lavish homes are diced up by trunks, with slim views of ocean sparkling through. The light falling through trees makes flickering, lacey patterns on the many dirt roads. As classically Maine as Southport looks in places, driving down these dappled driveways one feels as if she’s stumbled upon some kind of well-kept secret. A Maine dream come to life that you hardly dare speak of.