Venture into this cluster of five peninsulas—and the charming coastal communities on them—for an epic summer road trip full of lighthouses, gorgeous shoreline, and lobster.

By Annie Graves
July 20, 2017
Bailey Island
Photo: Sara Gray

I live, it turns out, to swerve. Along Maine's Route 1 as it pushes northeast past Portland, a flurry of signs crops up every few minutes or so, pointing off to the right. The names call out to me like voices from a New England literary fantasy. Harpswell, Boothbay, Pemaquid: These could be shipmates in Moby-Dick. Phippsburg and Georgetown: They sound straight from the landscapes of Hawthorne.

Those signs point, one at a time, to a tight cluster of five peninsulas. The geological quintet—jutting into Casco Bay like the prows of boats—is hardly an anomaly in this part of New England. Maine makes a habit of dangling peninsulas all the way up past Bar Harbor, almost into Canada. But this is a particularly dense bundle of promise. With no bridges linking them, each peninsula is a journey unto itself. And because so many travelers just stream along the coastal highway with destinations set and timetables established, this rich world is easily overlooked.

But not, happily, by me.


Photo: Sara Gray

The pace is instantly slower off of Route 1, meandering down Route 123 toward Lookout Point, where the 1761 Harpswell Inn overlooks tiny fir-peaked islands and a tangle of shacks, boats, and traps. Briny air sweeps the wharf at the end of the road. Seagulls dive-bomb the water. "Most wharves today are co-ops," says wiry Albert Rose, emerging from a gray-shingled shack draped with buoys at Allen's Seafood. His wide-legged stance implies waves, even on land. Who better than a man of the sea to tell me where to taste local catch? Erica's Seafood, he says, and I set my compass for South Harpswell.

The red-trimmed takeout stand, with its picnic tables and Crayola blue umbrellas, is thronging. The seafood cakes carry a spicy rémoulade, and the lobster roll is sweet and juicy. Lines don't lie. This is a mouthful of Maine.

It is also an eyeful. The tranquil harbor draws the gaze out and beyond. Is this the deep-breath serenity that explorer Robert E. Peary fell in love with years ago? His summer retreat on Eagle Island is just a 20-minute boat ride away on the Marie L. Time to find out.

Peary built his graceful gray-shingled hulk to look like a ship, but it's a time capsule, too, from his sheepskin expedition coat to his dark, woodsy kitchen that teleports me to 1909, when he claimed to reach the North Pole. I regard Upper Flag Island, where he let his sled dogs roam, and take in this landscape of islands. Though not a native Mainer, Peary grew up in Portland. "He found his love of exploring here," a docent says. I can see why.

Back on the peninsula, the Marie L. drops me at the front door of the Dolphin Marina and Restaurant, home of a famous lobster stew. I take a seat in the serene dining room; warm blueberry muffins appear without my asking. On a back deck, diners wait for their tables, sipping wine as lobster boats chug past Half Way Rock Lighthouse. No one minds the wait.

The next morning, I drive down Route 24 along a string of tiny gems: Great, Orr's, and Bailey islands. Land's End (it really is called that) on Bailey Island culminates in a gift shop, a weathered statue to Maine fishermen, and a 180-plus-degree view of the churning Atlantic, plucky sails, and cloudless skies.


Photo: Sara Gray

Hearing tell that Phippsburg holds a sweeping beach, I make it my destination No. 1 as I roll south along Route 209 toward Popham Beach State Park. It's a Maine beach day; the three-mile mirage of sand and softly sculpted rocks lit by golden sunlight is surreally beautiful. The water is a bracing 56 degrees, according to Ethan, the lifeguard. As soon as I lose all feeling in my feet, I find it's also incredibly refreshing. This is, in fact, how Maine's waters are enjoyed: shock, and then awe.

I crave a little history, so I dry off and journey to the terminus of Route 209, on a curling finger of land. Here stands haunting Fort Popham, built in 1862, guarding the passage to the interior. Shaped like a Roman amphitheater, this Civil War relic is a striking contrast with Spinney's Restaurant, a differently faded landmark across the parking lot with rustic signs and (it turns out) an outrageously tangy cup of haddock chowder. I'm only left wondering why I did not think to order a bowl.


Photo: Sara Gray

The route into Georgetown seems even more meandering than previous peninsulas, and I feel like I'm now double-detouring: out to find views from headlands, ducking into tiny galleries, and discovering hamlets that seem to exist only because of a legendary lobster shack.

On the peninsula's eastern flank, I settle in at the Coveside B&B and realize that it's the stuff of summer daydreams. It's a toss-up what I like best about it: my balcony overlooking Golf Cove, or the easy camaraderie of my hosts, who serve up strawberry shortcake at breakfast and plenty of marvelous recommendations.

Which sends me toward Five Islands Lobster Co. for what I've been told will be a defining seafood moment. But before that, it's a detour to Georgetown Pottery for a defining ceramics moment. This is indeed the stoneware mother lode: If it can be rendered in clay, then these potters have made it and adorned it with a Maine motif, from blueberries to birch trees.

The ultimate Maine motif, however, could be Reid State Park, which faces the wide expanse of the Sheepscot River. Beach roses fill the bushes. Sand sifts around mounds of stone that rise from the surface like antediluvian creatures. I wander the smooth and rounded shapes, watch the rangers patiently trimming back Maine's summer-hungry greenery along narrow paths, and dream of lobster.

When I arrive at the tiny clutch of harbor that holds Five Islands' fiery red lobster shed (and a small flotilla of lobster boats), I wonder if this spot may be the very heart of Maine. I order lobster, steamer clams, and mussels from the chalkboard menu, and savor the salty goodness of what grows in the deepest, coldest waters. Bay to basket, I think. Could there be any more rewarding gift in this peninsular kingdom?


Boothbay Harbor
Photo: Sara Gray

Up another peninsula, and then down again. Passing the bottleneck in Wiscasset on Route 1—a lobster-roll face-off between legendary Red's Eats (left side of the bridge) and Sprague's Lobster (right side)—I turn down Route 27 toward Boothbay Harbor.

Town is jumping, and my eyes leap from one diversion to another in this pretty port that's part fishing village, part resort. Shops and restaurants elbow for attention; boats steam to and fro with lighthouse tours, excursions to watch whales and puffins, or an escape to wild Monhegan Island.

Crossing Boothbay's harbor along the longest wooden footbridge in the country, I stop midway to inspect the 1902 Bridge House, rising on spindly legs out of the water. There's a man balanced equally precariously on a ladder, painting trim. I linger long enough to be noticed. "Want to see inside?" he calls out. Of course I do. This 720-square-footer is the ultimate escape—silvery shingles, wood-paneled interior, and the best curb appeal ever.

At day's end, I hop the Spruce Point Inn's water taxi for a ride home to my waterfront cottage. Our pilot points out the sights: Cuckold's Lighthouse, now a luxury inn, and Burnt Island (so named at the turn of the previous century, he says, because its owner burned it every spring for his livestock). The sprawling inn looms into view. A one-time haunt of the Kennedys, it's just far enough from the harbor bustle. I slide into an Adirondack chair as night falls, listening to the sounds of children laughing as they toast marshmallows. A graceful kayak cuts through the water down by the dock.


Photo: Sara Gray

Tangled up in Pemaquid—it feels like a fitting way to wind down a peninsula odyssey. This is Rachel Carson's backyard, and it is gloriously unspoiled. Although the pioneering marine biologist and writer of Silent Spring built her summer cottage on Southport Island in 1953, this is where she came to work: a quiet, beautiful salt pond on the shores of Muscongus Bay.

Today, it is the Rachel Carson Salt Pond Preserve on Route 32—still quiet, still beautiful. I linger for a while at low tide, captivated by the comings and goings of periwinkles and tiny crabs.

In fact, Carson is never far from my thoughts as I make my own discoveries. New Harbor has a few dandy surprises, including the Pemaquid Craft Co-op, filled with paintings, pottery, quilts, and jewelry by local craftspeople. Colonial Pemaquid holds the pensive ruins of Fort William Henry. I could explore for hours. I could explore forever.

So before finally facing the southern road home, a line that feels confiningly straight after days of dips and dodges, turns and out-and-backs, I decide to make one final stop: Pemaquid Point. Jutting into Muscongus Bay just south of New Harbor, it is the site of a lighthouse that bears its name. Commissioned by John Quincy Adams, the 1827 Pemaquid Point Lighthouse presents a scene so iconic that it's pressed onto Maine's state quarter. It's everything it should be. Craggy rocks. Cold blue water cut with foam. A brilliant, white lighthouse framed against a lighter blue sky. I can't resist. It is a last happy swerve off the map.


A half-hour northeast of Portland, coastal Route 1 posts exits to peninsulas every two to 14 miles.


The Harpswell Inn overlooks a stunning cove and working wharf, with sloping lawns to the water. Rates start at $150; On Georgetown peninsula, you're guaranteed a water view at the stylish Coveside B&B. Rates start at $205; Convenient to Boothbay Harbor via water taxi, the Spruce Point Inn is family and pet friendly, with children's programs, kayak tours, and a spa. Rates start at $135;

Annie Graves is the home and garden editor for Yankee magazine. She lives in southern New Hampshire, but spends part of every summer in Maine. This is her first story for Coastal Living. This story originally appeared in the July/August 2017 issue of Coastal Living.

Photos: Sara Gray