Jaunt From Portland: A Maine Coast Weekender

A Day In The Way Life Should Be

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The state slogan can be an intriguing first peek into the local mindset, a window of opportunity to get a flavor for their world by seeing how they see themselves: “Smiling Faces. Beautiful Places.” (South Carolina), “Mile after Magnificent Mile.” (Illinois), “It’s Like A Whole Other Country.” (Texas) and the wonderfully self-explanatory “Virginia Is For Lovers”. And then there is Maine’s: “The way life should be.” It’s the quiet Mainer confidence we’ve come to love, a simple statement of their facts as they know them to be true. Portland being a seafarers’ town of expeditionists triggers an adventurer’s reflex, so we were naturally inclined to road test Maine’s motto for ourselves (albeit via fire red Beetle and turnpikes, versus lithe schooners slicing through whitecaps). Forthwith, we expand on this catchy little truism, adding some of the discoveries gleaned from our day of coasting.

Seeing The Light… As It Should Be

“Be mine to guard this light from all eclipse; Be yours to bring man near to man.”

– Henry Wadsworth Longfellow

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With over 65 historic lighthouses standing watch over its majestic shores, Maine has earned its reputation as a destination for beacon seekers. They come in all forms – stout, conical, square, statuesque – but inspire uniform awe imagining the storms weathered, the shipwrecks averted, and the hope still symbolized today. An anticipatory drive past South Portland’s august waterfront mansions delivers you to the Portland Head Light and Fort Williams Park, its verdant backdrop. Perhaps the most emblematic of lighthouses, its station atop a jutting curvature of coastline is complemented by open-mouthed views in all directions. The Head Light’s 200 years of service to sailors on unpredictable seas is marked by plaques honoring the Keepers of the Light, and a makeshift shipwreck memorial is a reminder of the mercurial nature of its duties. The rumored inspiration for Longfellow’s “The Lighthouse” seems a most worthy subject of tribute. In the distance, you can spy the Ram Island Ledge Light, a functional counterpoint in the lighthouse architecture study. Next, a sun-mottled southbound trip to Cape Elizabeth leads to Two Lights, an active lighthouse on the rocky headlands atop Dyer Cove. The picturesque scene pairs perfectly with lobster roll boats (more on that in a moment). Finally, one of our favorite new discoveries this time around was Cape Porpoise and its Goat Island Lighthouse, winner of what has to be the best seats in the house for beholding the Cape’s epic sunsets.

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Head-to-Head Competition… As It Should Be

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A cursory Google search on the topic of best lobster rolls will plunge you headfirst into a land of feisty debates on the subject, every roadside stand and lunch counter prompting an intense fealty among their local contingent. For visitors this proves quite the boon, inspiring us to set out on a ‘lobster roll trail tasting’ in search of THE ONE. We spent the better part of a week taste testing the very best renditions of the New England delicacy (hey, someone had to do it), and while we can truthfully say that we never had a version that wasn’t outstanding, these were some area standouts.

J’s Oyster

5 Portland Pier, Portland | (207) 772-4828

You smell J’s before you see it, following the scent of greasy spoon glory down a hazy alley until you’re deposited onto a working wharf.  There, a nondescript white box of a place with midcentury scrawled signage awaits you, packed with loyal regulars elbows-deep in either ‘dollar a piece’ oysters or a marvelously simple lobster roll. The traditional hotdog bun piled high with cold, juicy meat is hardly a study in refinement, but who wants refinement when they could be halfway to a deliriously happy lobster coma? Certainly not us. 

The Lobster Shack at Two Lights

225 Two Lights Rd, Cape Elizabeth | (207) 799-1677

Reigning above Cape Elizabeth’s watery edge is the venerable Lobster Shack at Two Lights, a triumphant blanket of picnic tables and lobster glory. Locals grumble about the traffic and the expense and we can see their point. But chowing down on the Lobster Roll Boat to the rhythmic bleat of the foghorn while watching the tides roll proved to be a pretty singular scene we recall with vivid fondness. 

The Clam Shack

2 Western Ave, Kennebunk | (207) 967-3321

The lobster roll champ in almost everyone’s opinion, we humbly add ourselves to The Clam Shack’s list of gushing faithful. Sitting on their picnic benches near the Taintown Bridge feels, in the best possible way, like lunch in a simpler time. There is no need for fancy sauces or a mountain of condiment (though of the mayo or butter option offered, we enthusiastically chose the latter). The Shack serves meaty piles of steaming, fresh-picked lobster on (round!) buns in regimented, perfect proportion so blessedly, they simply let the sweet crustacean shine. 

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The Afternoon Drive… As It Should Be

Driving Maine’s scenic backroads and turnpikes illustrates its designation as “vacationland”. The route from Cape Elizabeth to Kennebunkport is not only a feast for the eyes, but for the imagination, its farm scenes and antiquer’s trails warrant detouring for a pit stop.

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Strolling… As It Should Be

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Some discount Kennebunkport as a Disneyana version of Maine but we were utterly charmed by its smalltown chic. (If it’s good enough for former presidents, it’s good enough for us!) With narrow streets built for ambling, you’ll find an abundance of enchantments along your way. Some standouts:

Rococo Artisan Ice Cream

6 Spring Street, Kennebunkport | (207) 251-6866

Rococo had us at their pretty storefront and germane description: “Inspired by travel, Made in Maine”. The flavors, however, need no cute tagline assistance. We can confidently attest that Goat Cheese & Blackberry Chambord Swirl, Sweet Avocado Cayenne, Spicy Rocky Road, Maine Maple Walnut and local favorite Whoopie Pie hold up all on their own.

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3 Dock Square, Kennebunkport | (207) 204-0275

Despite its small size, Minka is such a well-curated showcase of locals-only jewelry, beauty and housewares that we had to make an effort not to overdo it. Handmade Michelle Rose leather clutches, a soothing, eponymous beauty line, stunning birchware pottery and dainty pearl jewelry are just a few of the Maine-made wares that caught our eye.

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Daytrip Society

4 Dock Square, Kennebunkport | (207) 967-4440

Given our real-life daytripping status, we were delighted to stumble upon Daytrip Society, a brilliant offering of all-star goodies from both local artisans and national brands. Its creative categorization (see: Daytripping and Maine) confirmed our sense that we’d come to the right place. 

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Sunsetting… As It Should Be

The Ramp

77 Pier Road, Kennebunkport | (207) 967-8500

Nunan’s Lobster Hut

9 Mills Road, Kennebunkport | (207) 967-4362

At the behest of our in-the-know (and lifetime Kennebunkport-summering) friends, we found ourselves winding down our day in Cape Porpoise: “what Kennebunk used to be.” A rad little fishing village that pulls no punches, we moseyed on down to the end of the cove to catch some reel live fishing action before snagging a pair of yellow Adirondacks at The Ramp. We were powerless to resist the lure of the sports ephemera-adorned bar, and taking in the rainbow sherbet sunset from their front row seat was one of the highlights of our day. For fresh lobster prepared just about any way your heart desires, head to local legend Nunan’s Lobster Hut, a third generation treasure specializing in premium seafood and a homey setting. 

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Retreating… As It Should Be


The White Barn Inn

37 Beach Avenue, Kennebunkport | (207) 967-2321

After spending the day lost in this seaside township’s many pleasures, you’ll be tempted to stay awhile. Luckily, you’ll find two high-end accommodation options at your disposal. The Relais & Châteaux White Barn Inn is a romantic application of understated luxury, effortlessly balancing its 145-year history with modern comforts. The much-lauded onsite Restaurant is housed in the resort’s namesake barn and its local-centric tasting menu is a justified splurge.

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Hidden Pond

354 Goose Rocks Road, Kennebunkport | (888) 967-9050

The yin to The White Barn Inn’s regal yang, Hidden Pond is an elevated Indian Summer of a hideaway, a collection of cottages scattered across 60 acres of waterfront forest. It’s a familial but upscale summercamp setting with activities galore at the constant ready. The ‘farm to fork’ menu at the venerable Earth restaurant is well worth the price of admission. The rustic dining room is the perfect complement to Hidden Pond’s aesthetic, and the proximity to the walkable gardens a welcome post-dinner perk.

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Contributing Photography: Helen Brooks

© The Gather Maine coast Guide: What to do on the Maine coast, Coastal Maine weekender.