At first sight of the postcard-style images of an Olympic-sized saltwater pool at the edge of a rocky harbor, I’m ready to jump in. The “Deep End” lettering on the far wall looks like it’s out of a Wes Anderson film. The pool of filtered seawater from the chilly, nutrient-rich depths just down the ledge is part of Sebasco Harbor Resort, a classic summer retreat on one of the peninsulas and islands jutting toward the open Atlantic between Freeport and Rockland.

The resort’s coastal Sagadahoc County location is unfamiliar territory for me, which adds to the anticipation, and we make the drive to the coastal getaway on a rainy day in August to stay for a couple of nights. Photographer Peter Frank Edwards, my partner in such adventures, is at the wheel. We pass through the shipbuilding city of Bath and across the bridge and causeway over Winnegance Creek. Our destination is a dozen miles farther down the spine of the Phippsburg peninsula—nearly a straight shot across Casco Bay from Portland. Trees along the road are at their fullest leafy green in the wash of summer rain.

A driveway into the 450-acre resort takes us past cottages and golf greens, and we stop at the registration office to check in and look through a listing of the week’s activities: yoga classes, tennis round robins, ice cream–making sessions, golf clinics for kids, and campfire sing-alongs. Now I’m reminded of movie scenes again—this time the 1960s resort in Dirty Dancing, that classic summer film with Patrick Swayze.

SEAGULLS AND SIPPING

Next on the resort’s lineup, a wine tasting is starting within the hour. But first we stop by the cake-tower of a structure where we’ve booked a room. The four-story, octagonal building with a cupola on top was intended to be a lighthouse when it was built in the 1940s by the resort’s founder, but it was never commissioned or equipped with an official guiding light. For daylight direction-finding, however, the unusual building is a beacon. We climb the stairs to the large third-floor room where we’ll be staying. There’s no AC in this building, but breezes and fans provide plenty of air, and wide windows give us views overlooking the dock and sailboats in Sebasco Harbor on the New Meadows River.

It’s all about vantage points here. To see more, we clamber up the stairs to a lookout room on the floor above that’s furnished with striped couches, wicker chairs, and benches. There are board games on the tables, and windows stretch across every wall. You get a 360-degree view here, and it’s obviously a popular hangout. Guests have written their names on the walls: “Allison loves Kurt,” “True Love Always,” and dozens of other names and quick sketches marked with dates and years spanning more than a decade.

Looking out from this den-like common area, I come face to face with a seagull perched on a windowsill just outside. The bird, nonplussed, calmly eyes me and steps away. Minutes later, as we walk to a nearby building for the wine tasting, a family of several generations is in front of us, and I see what looks like that same gull again on a nearby rock. “Fred! Fred!” the kids are shouting and pointing. They recognize him, too.

The tasting room is set with tables of cheeses, fruit, and wine—it’s as casual and easygoing as a house party. “There’s not another place like this,” says Lauren Ault, who’s pouring the wine for guests, and says she enjoys the peninsula and the family-owned resort so much she ended up buying property nearby. A representative for a wine distributor, she mentions that some of the wine we’re sampling is from Dry Creek Vineyard in Sonoma County, California, a vineyard that has a Maine connection. The owners, she says, often sail the coast of Maine in summertime. “They’ll come in right here,” she says, pointing toward the water.

PARK THE CAR

We have early reservations at the Pilot House Restaurant, which is also in walking distance, like most everything on the resort. Providing opportunities for physical activity has been part of the resort’s mission since its founding more than nine decades ago. That’s when Nathan Cushman bought the property, envisioning a recreation-based resort instead of one built around sedentary vacationing. He built the golf course and bought boats for tours and fishing. When his son and daughter-in-law took over, they added the seaside pool.

The Ledges Pub is filling downstairs when we arrive before sunset, and in the upstairs dining room Glenn Miller and Frank Sinatra tunes are playing. The hostess mentions that most tables are full because it’s a big date night for couples staying at the resort with their children—most kids have headed over to a pizza and bowling party in another building. Meanwhile, as the dining room buzzes with conversation, we tear into soft rolls and try the cauliflower soup, tuna tartare, and a haddock and crabmeat dish that’s topped with a really good beurre blanc sauce. Vintages we tasted earlier are on the wine list, in case guests tasted one they like. We did, and I order a glass of the Dry Creek fumé blanc.

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The meal is our pre-game for trying some bowling ourselves. We walk over to the Quarterdeck, a long wooden building that looks like a barracks or chicken barn and is glowing with light from inside. We follow the sounds of young voices, pinball machines, table tennis, and bowling. Two of the four lanes of candlepin bowling are out of service and closed, but the other two are in full play. I’ve never tried this style of bowling, which is the traditional form in Maine, and we sit in the bleachers behind the lanes to watch for a while first—but mostly because there’s a waiting list to play.

“This is so different from regular bowl-ing,” I say to Peter Frank, and a resort guest nearby says with a smile: “No, this is regular bowling.” In this New England version that dates to the late-1800s, the ten wooden pins are narrower, and the balls smaller—about the size of a big grapefruit. The scoring is on paper here, and there’s some simple math involved to tally each player’s points. I learn all of this from the attendant who’s minding the lanes tonight, and from kids and adults nearby. One couple says they come to bowl every night of their weeklong stay, every year. Not only because I rolled a strike or two, I’m a new fan of this retro game.

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LOBSTER LAWN PARTY

The next day is the weekly lobster bake at Sebasco Harbor Resort, and we see the staff make preparations throughout the afternoon. Tables are set up in a grassy area near the pool, and a large wood fire is built and burned until the coals glow. It’s where the lobsters will be cooked, along with eggs in the shell, sausages, local red potatoes, and mussels. On side tables, bowls and plates with salads, blueberry pie, watermelon, rolls, clam chowder, and coleslaw are arranged, and there is a grilling station for steak, burgers, and hot dogs. A live band plays country dance tunes as the sun gets lower, and a caller gets many of the guests to their feet.

The host of the bake is Bob Smith, the resort’s owner since 1997, who makes the rounds to talk with everyone who’s gathered for the bake. He’s just back from an afternoon softball game—one of the guest activities he typically joins. He and his wife are only the fifth owners since the resort’s founding as a lodge by the sea. And all the owners have been individual couples or families who take part in operating and maintaining the place each year along with longtime staff.

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The next morning we meet a couple of legendary old-timers at the “Repairatorium” workshop. It’s the domain of two brothers who’ve run the resort maintenance and fix-it shop since the mid-1950s. “They grabbed us right out of high school, and we’ve worked for all of the owners,” says John Totman. He and Owen Totman are jacks-of-all-trades, and a trove of resort history. It’s easy to see that they also share a dry wit. They want to know if we’ve seen them driving the resort’s modern trash truck, or starting the fire for the lobster bake, or filling in as crew on the tour boat. They also often help guests with broken items. Eyeglasses, shoes that have come apart from their soles, and plenty of broken bicycles have come through the shop. Fishing reels can be a pain, they say, but the garage doors are open most days for people who stop by to eye the tools and workbenches on their way to the ice cream shop next door. The brothers have gotten to know generations of guests’ families. “Sometimes we’re asked to take the training wheels off of kids’ bikes,” Owen says with a wry smile. “And then we shove them out the door.”

At the lobster bake, other guests suggest we hike Merritt Mountain, and before nightfall we follow the trails directly from the resort. Along the way, we get to Robinson Rock (locally called the “Bumpah”) at 205 feet of elevation, and continue to the summit, a little higher at 233 feet. Both provide spectacular views of the islands in Sebasco Harbor and the eastern islands of Casco Bay. Surveying the scenery, I’m sure Fred the seagull’s down there somewhere.

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POOL BEACH BOAT

On our final day at Sebasco, the sun is bright, and we make the most of it. We get in the car to explore a little more of the peninsula then head to Popham Beach to walk along the shore and see the driftwood day-forts made by beachgoers near Spinney’s Restaurant, just over the dunes. Then there’s the worn stone walls of a Civil War–era fortification, Fort Popham, just down the shore at the mouth of the Kennebec River.

Back at the resort, we take a boat cruise on the Ruth, Sebasco’s tour boat and supposedly the oldest continuously operated passenger vessel in Maine, for views of stacked lobster traps and fishing boats at Cundy Harbor and the shoreline along the New Meadows River. It’s been an extraordinary year for seeing schools of menhaden fish and the seals that follow them, says Captain Phil Luedee, another Sebasco long-timer who says he has been visiting the resort and piloting the Ruth for most of his life. And finally, we spend some time poolside. Before I take the plunge, we meet a young couple from North Carolina. The woman says the water feels too cold for a swim. The source of the pool’s water is the bay just beyond the stony embankment. Her boyfriend, who mentions that his dad and sister worked here when they were teenagers, and that he has been visiting since he was a kid, isn’t tentative at all. He jumps right in at the ten-foot end, and when he surfaces he calls out: “It’s perfect!”

PLAY ALL DAY:
SEBASCO OVER 90

Early guests at this independently owned, seasonal getaway founded in 1930 on the Phippsburg peninsula included Eleanor Roosevelt and jazzman Benny Goodman. Sebasco Harbor Resort spans some 450 acres and offers lodge rooms, suites, and cottages—from historic lodging to modern rooms with AC. A chock-full schedule of family-friendly guest activities is offered each day in the summer season, from tennis lessons and scavenger hunts to spa treatments and cooking demos. There’s also a golf course, dock and moorings, dining at the Pilot House and Ledges Pub, and a cafe and ice cream shop.