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Trip Ideas

A Summer Road Trip In Southern Maine

Maine regular Sarah Horne Grose reminisces about her first visit to Vacationland and shares the ideal route for weekend road trippers

It was after midnight when our borrowed, battered green Volvo rumbled over the Piscataqua River Bridge. ‘State Line. Maine. Vacationland…’ read the sign.

This was a decade ago, and as we drove across the border my husband, who had grown up visiting Maine with his family, blasted Bad Company on the tinny vintage radio that teetered on top of the dashboard. It was a funny, oddly romantic moment: late summer, leaving the crammed, hot city behind us, with the pine trees on either side of Route 1 looming large in the darkness around us, and kitschy classic rock filling the quiet as we headed north and the fog rolled in.

What’s stuck with me ten summers hence is that there is always magic in the moment you arrive in Maine. There is the anticipation of so many unadulterated pleasures: American flags flapping in the breeze; the dark silhouettes of wind-battered islands against slate-blue water; unlocked doors and bare feet; wild blueberries and lobster boats plying the bitterly cold ocean swells. {"type": "left-quote", "text": "What’s stuck with me ten summers hence is that there is always magic in the moment you arrive in Maine."}

When the ‘summer people’ arrive, they often decamp to family cottages and compounds in insular seasonal communities, leaving their little enclaves only to buy important provisions like hot dog buns and fleeces from L.L. Bean and cases of Sancerre. There are cocktails on the porch (until the mozzies come out), the men in pressed shirts and sherbert-hued trousers. And of course, there is all the tennis and swimming and sailing and picknicking, the sorts of tradition-bound pursuits that have endured since the cottage people first whiled their way to Maine in the 19th century.

But there is also a beauty in being a newcomer here, unfettered by invites and ironing boards in the formidable state of Maine. Ambling on the wilder back roads or finding remote ferries and buying a one way ticket is half the point. Cell phone service can be mercifully spotty. There are libraries that open for three hours a day, and honor boxes at roadside stands selling fresh eggs or corn. Hikes through forests strewn with fairy houses; scads of seals basking on rocks.

On this year’s adventure, Portland is our first port of call, a cobbled, hill-perched city full of handsome old warehouses and winding passageways. We hatch schemes to polish our Stand Up Paddleboarding skills with the Maine Surfers Union and pop into The Holy Donut, on Exchange Street, for Maine-made dark chocolate sea salt donuts and iced coffee. Clearly we are not going to go hungry. Lunch brings us to Eventide Oyster Co. It’s an airy, urban setting, but the names of the local oysters feel timeless. Norumbega, Basket Island, Flying Point, Wild Belon, Ebenecook. Served up with a mean Celery Gimlet.

After a ramble through the historic village of Yarmouth and a spell ogling the sprawling estates on Cousins Island, we hop on one of the Chebeague Transportation Company’s ferries, the Pied Piper, which is packed with families decamping to this long, flat Casco Bay island for the season, their dogs and children looking bemused as they stare out to sea. {"type": "right-quote", "text": "There are 3,478 miles of Maine coastline to explore. That’s more oceanfront than California."}

We stay at the Chebeague Island Inn, with its deep porch and Adirondack chairs on the lawn overlooking the manicured Great Chebeague Golf Course. The rooms, with whitewashed wooden floors, feel much as they would have when the current structure was built in 1924; there are warm chocolate chip cookies served in the lobby in the afternoons and cruiser bikes on loan. There are sandy beaches to explore, yet it’s easy to get lost gazing out to the bay as a herd of little boats sway in the breeze.

It’s hard to pack up and leave so soon but we feel beckoned to head north, winding our way up and down the peninsulas of mid-coast Maine. There are 3,478 miles of Maine coastline to explore (that’s more oceanfront than California, by the way.) That’s where we spy two great blue herons in flight over a pristine, empty cove and hike past ancient oyster shell middens. It’s also where we happen upon the winsome Pemaquid Beach, a sliver on Johns Bay with a campy-cool snack bar that makes you feel you’ve stepped back into the 1950s. The birds overhead are beginning to fly in formation, a hint that summer will soon be over, sending us back south to the city and its stresses.

Until then, we’ll raise another Dark & Stormy to the way life should be, getting lost in the countryside, gorging ourselves on oysters, and finding new escapes further and further off the beaten path. When you hear the strains of ‘Feel Like Makin’ Love’, think of us heading north over and over again, hoping the car doesn’t break down.

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Saltwater Farm Cooking School & Cafe

Fancy learning how to make the quintessential blueberry cobbler, crusty loaf of bread, or planning your very own culinary garden? Saltwater Farm is a coastal Maine cooking school in Lincolnville, Maine, founded by foodie Annemarie Ahearn. Guests can visit for special classes as well as several day workshops, all the while living out the ultimate back to the land fantasy. If you’d rather just taste the bounty of local, seasonal fare without getting your hands dirty, head to Salt Water Farm’s chic, rural modern eatery at Union Hall in Rockport, Maine.

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Coastal Maine Botanical Gardens

Take in the beauty of Maine’s lush greenery and stunning flowers at this Boothbay idyll, which comprises 270 acres of shoreland, forest trails, and manicured gardens. Youngsters will adore its magical Children’s Garden, complete with a treehouse, play kitchen, chicken coop, maze, and pond, while adults relish the beautifully groomed trails, meditation garden, and water views. In late summer, the gardens’ lush hydrangea and clematis are in full bloom. Visitors can join a tour by sea kayak as well.

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Schooner Landing

There are plenty of dockside restaurants and bars in mid-coast Maine, ensuring that al fresco cocktail hours never get old. Schooner Landing, located in the historic river village of Damariscotta, is one of the best, with live folk music on the deck most nights and a raucous, everyone-is-welcome vibe. On some summer evenings, local oysters (some of the best in Maine) are free. What more could you ask?

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The Standard Baking Co.

Portland, Maine has become a destination for serious foodies, and they’re spoiled for choice with restaurants like Eventide Oyster Co., Fore Street, and Street and Co. If you’re just passing through, a must-see is The Standard Baking Co. in the Old Port district. With fresh croissants, serious baguettes, and indulgent sweets, you can’t really go wrong. Afterwards, head to one of the city’s hip new coffee joints, like Tandem Coffee Roasters with its Brooklin-in-Maine ambiance and very cool clientele.

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Owl & Turtle Bookshop & Cafe

Camden, Maine is rife with galleries and laid back yet stylish independent businesses. Among them, Owl & Turtle stands out for its well-curated selection of summer reads, its charming childrens’ books section (ideal for rainy days), and its sweet coffee shop, which serves pour overs and delectable baked goods. Look out for the very cool selection of food and design magazines, perfect for inspiration for your future summer house.

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Monhegan Island

Monhegan Island is one of Maine’s most dramatic and unspoilt islands, reachable only by ferry from the village of New Harbour. Since it was discovered by John Smith in 1614, its come into its own as a fishing community, artist’s colony, and one-of-a kind escape from the mainland. There are no cars on the island; instead visitors can hike some twelve miles of showstopping trails. Afterwards, it’s time for refreshments at The Barnacle cafe or drinks on the porch of the old-fashioned Island Inn.