T+L explores the unexpected pleasures of returning to a summer vacation place year after year—in this case, Maine.
| Credit: © JOHN C. DOORNKAMP / Alamy

The Piper Cub buzzes back into view, flying just 200 feet over the waves, its red-lettered banner unfurled behind. All afternoon it’s been crisscrossing the cloudless sky. Every day, the same plane, same offer: Ken’s Maine Clambake – $19.95. When I first started coming here, the price was $8.99. Back then I could read it without my glasses.

Each time the plane passes, the kids on the beach look up from their pails and shovels and cheer. (Today, our friends’ son Silas is building a sand replica of Fenway Park.) Soon there will be Popsicles, a game of four square. And later, as the tide comes in, we’ll round up our blankets and shuffle over the dunes to the house, to start the evening ritual: fixing Maine Route 1 cocktails, shucking corn, steaming lobsters, plucking basil from the window box, making sea-urchin pasta. After dinner we’ll have a round of Bananagrams while the Sox game plays on AM radio. If it’s chilly there might be a fire—though we’re as likely to doze off before 10, sun-drenched and surf-pummeled as we are. In the morning the gurgle of coffee will coax us from bed at dawn, and the whole routine will begin again.

I’m not sure how it started, and I can’t say when it might end, but we’ve been making this trip together for more than a decade, my wife, Nilou, and I and this group of friends. It’s become, unexpectedly yet unchangingly, What We Do. Every August, we stuff our cars with iceboxes and inflatable rafts, sharp knives and good wine, and point our caravan northward for the annual migration to Pine Point.

There may be prettier beaches, with quainter towns beyond, some on this very Maine coast. Yet this is the one I daydream about, through drizzly Aprils and slate-gray Decembers. I wouldn’t necessarily have chosen this place, given my pick of a thousand others, but years ago this place chose me, and it’s lured me back every summer since, so I guess it’s settled. We’re together for the foreseeable future.

My friend Mark and I have known Pine Point since we were teenagers; his parents, the McAdams, own a summer cottage just upshore from our rental. It was my idea to bring the group. Until their first visit in 2001, Nilou and the rest had never been north of Boston—couldn’t crack a lobster, couldn’t name a single Red Sox. In the years since they’ve become localized, loyalized: converts to the cult of Maine.

Constancy is the most underrated of virtues, in people but also in places. You can revisit London or Tokyo every six months and find an entirely new city in place of the one you remembered, such that even your 18th trip feels like a first date. Returning to Pine Point, we find everything as we left it—as if we’d merely stepped out for a Dr Pepper in the middle of a game of paddleball, then returned, 358 days later, to resume it.

Set on a peninsula south of Portland, Pine Point is a cluster of rustic cottages and slightly grander Victorians set along a series of cul-de-sacs jutting off the main road toward the sea. At the end of each cul-de-sac is a sandy footpath that cuts through a deep ribbon of dune grass that hums with dragonflies and ripples in the breeze. And at the end of the path, where the tallgrass falls away, lies a seven-mile crescent of flat, smooth, sand-colored sand.

Our first walk of the season down that path—a barefoot trudge weighed down by sloshing coolers and salt-scarred beach chairs—may be the happiest moment of my year. That it requires a bit of effort and patience only adds to the drama. The tallgrass feels like some magical green barrier that must be breached, while the slight incline of the dune means you can hear and smell the ocean before you actually see it.

The house we rent isn’t much to look at from the outside, and entirely too much to look at on the inside, what with the owners’ ever expanding collection of beach kitsch. But it’s our place, and through the years that’s come to mean a lot. Were I a first-time renter arriving today, I might take issue with the abundance of crab figurines, the rather lumpy beds, the rusty taps and hinges on the outdoor shower. But the shower itself? No marble-clad bathroom could compete.

Our routine is quite simple: Swim. Nap. Eat. Rinse. Repeat. The start of the week is customarily filled with discussions of all the activities we might finally get to this year: a sailboat charter in Kennebunkport; a hike up Mount Agamenticus; perhaps a jaunt up to Rockland—but really, who are we kidding? We’re not going to do any of it. And when the end of the week comes, we won’t regret a thing.

Instead we find more modest diversions. Long beach-blanket grocery lists are made, elaborate meal plans hatched. There is the occasional detour to Portland’s Standard Baking Company for their unspeakably good brioche. At some point we’ll paddle kayaks into the nearby Scarborough Marsh, slipping through reed-walled channels while herons and ibis eye us from the banks. And should we ever tire of the quiet—or crave penny candy—we can always ride downshore to Old Orchard Beach.

On summer weekends, when 100,000 revelers descend on the place, Old Orchard officially becomes the largest community in Maine. It is also, semi-officially, the tackiest place in all of New England: a honky-tonk playground of flip-flop shops, fried-dough stands, temporary-tattoo parlors, and carnival rides that makes Ocean City, Maryland, look like the Henley Royal Regatta. Needless to say, we love it. The Grand Trunk Railroad used to run here direct from Montreal, and Old Orchard remains catnip for vacationing Québécois. The fried-dough stands also sell poutine; signs at the amusement park are in English and French. This provides a semblance of cultural displacement: batting cages become cages des frappeurs; Jet Skis become scooters des mers; while Skee-Ball becomes, charmingly, le skee-ball.

As a younger man I was flummoxed by people who returned to the same place every year. What were they afraid of? Didn’t they know there was more to see? Travel, I insisted, was about the unfamiliar, the undiscovered, the passport full of stamps. I still believe that last part, if less adamantly now. What I’ve awoken to since is the soul-affirming joy of returning. Going back, it turns out, does not mean retreat. A ritual is not a rut.

I’ve also learned the difference between traveling and vacationing, two words that are often used interchangeably but mean different things. A vacation typically involves travel, but travel is not always a vacation. Sometimes it’s quite the opposite—fraught with uncertainty over where to go, where to stay, what to see. Vacations are a respite from all that. For us, Maine is sweet relief.

Over time, and through the McAdams, we’ve come to know our neighbors. Each morning the residents of Pine Point gather on the otherwise empty beach, with their dogs and their coffee mugs, to discuss last night’s humidity or Ellsbury’s stand-up triple. Although we’re still technically “from away”—I suppose you could call us 1/52 local—they welcome us into their klatches, in part because we too are holding ceramic coffee mugs. We’ve also become enthusiastic patrons of the neighbors’ kids’ lemonade stand, a smart little dune-side palapa that they’ve festooned with homemade thatch. And we are on a first-name basis—we don’t know their last names—with the staff at Bayley’s Lobster Pound, where we have a standing order each evening for a half-dozen females.

Now and then we’ll spot the shambling figure we call the Clam Man, a grumbly chap with a spongy beard, leering fish eyes, a coral-like complexion, and the bearing of an insane Poseidon. He appears only at low tide, loping down the beach with a bucketful of just-harvested surf clams, their long oily tongues protruding from shells the size of Nerf footballs. The local children watch him from a distance. I spoke to him once—he answered in French, then grumbled off down the beach.

And so it goes, the same characters making their exits and entrances, the scenery and plotline seldom changing. Nilou once likened our Maine trips to rereading a favorite novel: she already knows how it will end, but getting there is still as satisfying, if not more so, since she’s always picking up new shades and nuances along the way. (The Clam Man is Québécois!) And, as with a cherished book, there’s no risk of disappointment—unless it rains all week, which some years it has. In that case we play a lot more Bananagrams.

Of course, things do change in Pine Point. Against a familiar backdrop one notices all sorts of quotidian adjustments, like when the snack bar gets a new sign, or the pier is painted a slightly deeper green, or coconut water makes its debut at the local grocery. These subtle shifts-of-the-light keep us on our sandy toes, while reminding us how lucky we are to have found a place that’s stayed, in most respects, pretty much the same. Our friend Michael put it best last summer: “There are few things you can rely on in this world, and thank God Maine is one of them.” Every visit is a sort of homecoming.

Anyway. I’m off to pack the cooler. Maybe I’ll see you on the beach.

This ginger-y summer drink—invented by our Pine Point crew—has become a key step in our post-beach, pre-dinner ritual.

• In a cocktail shaker, muddle three sprigs of tarragon with a pinch of turbinado sugar and the juice of half a lime.

• Add 4 oz. Hendrick’s Gin and plenty of ice. Shake well.

• Add 4 oz. Maine Root Ginger Brew and a splash of seltzer, stir, and strain into two highball glasses filled with ice.

• Garnish each with sliced cucumber and a sprig of tarragon.