Summer’s Maine Event

A tale of two (coastal) cities: Portland and Kennebunkport make for memorable New England getaways

The Inn by the Sea and Portland Head Light landmark are musts during your Maine trip. Photography: ISTOCK

The Inn by the Sea and Portland Head Light landmark are musts during your Maine trip. Photography: ISTOCK

Maine’s nickname is Vacationland, and this state—covering more than 35,000 square miles in northern-most New England—lives up to the moniker with a vast number of travel experiences, from hiking a slice of its 17 million forest acres to visiting one of its 300 museums.

But it’s the invitation to frolic along its 3,500 miles of ruggedly beautiful coastline that helps define Maine as a premier summer playground. Between June and August, temperatures are delightful, the Atlantic is (relatively) warm and days and nights are easily filled with all manner of pleasurable pursuits, in, on and around the surf.

Two cities on Maine’s southern coast stand out for their warm-weather welcome and great getaway potential: Portland, a unique urban oasis, and Kennebunkport, a quintessential New England beach town. Welcome to Vacationland.


The state’s largest city, Portland is as cosmopolitan as it is charming. Located on a peninsula with a working waterfront, historic Old Port and funky arts district, Portland is distinctly itself, with centuries-old buildings, cobblestone streets, only-here boutiques and tempting restaurants that serve everything from Maine lobster rolls to Mexican tacos. It’s a walkable city, seemingly designed for exploring, with an interesting gallery, museum or architectural artifact (and sometimes all three) around every inviting corner.

Where to stay: Just 15 minutes from downtown Portland, Inn by the Sea seductively combines luxury and nature, with 61 lavishly appointed guest rooms, suites and cottages, and nationally recognized earth-friendly practices, such as its LEED Silver-certified spa offering a score of sea-inspired treatments (think a “Sea Waves” massage with soothing strokes synchronized to the sounds of the surf). Flawless for couples in need of alone time, or families looking to have fun together, the inn boasts all manner of thrills, from early-morning yoga to nightly fire pits—and, thanks to its sublime spot on Cape Elizabeth’s Crescent Beach, a short stroll along a private boardwalk is all the effort necessary to be transported from the warm embrace of the inn to the wide expanse of the ocean. Fuel up for each day of fun at Sea Glass Restaurant, with its ooh-and-aah water views and breakfast, lunch, dinner and weekend brunch menus that fuse local and healthy with utter deliciousness.

What to do: Walk or run Back Cove, a scenic exercise trail that loops 3.5 miles around an estuary basin in the shadow of the Portland skyline; take a cruise with Wine Sails, a wine class on a 74-foot sailboat that plies the waters around Casco Bay with toast-worthy coastline views; or take a shining to Portland Head Light in nearby Cape Elizabeth, the oldest lighthouse in the state. Also, be sure to cheer for the local minor league baseball team, the Portland Sea Dogs; and—if you’re visiting on the first Friday of the month—stop by local art galleries, studios and museums during the First Friday Art Walk, where participating venues stay open late, often with local artists on hand.

Where to shop: Portland’s many boutiques are an ever-present temptation—there are around 160 in Old Port alone. Bargain-hunters will be lured 20 minutes north to the town of Freeport, with its plethora of name-brand outlets, including Cole Haan and Patagonia, as well as the flagship store of outdoor outfitters L.L. Bean, which is open 24 hours a day, 365 days a year.

Where to eat: For breakfast, get caffeinated with a hand-crafted, micro-roasted cup at Coffee by Design and then speed-walk over to The Holy Donut for exceptionally delicious donuts made with Maine potatoes. Have lunch at Green Elephant, with its carnivore-converting Asian-inspired vegetarian fare and savor a locally sourced and expertly crafted dinner—ordered off a menu that changes daily—at Fore Street. For dessert, pick up a few hand-dipped truffles at Dean’s Sweets.

Not-to-miss summer 2015 events: Kick off summer at the Old Port Festival (June 14), with music, Maine-made crafts, a street-long buffet, kid’s activities and even a parade; celebrate yoga and overall wellness with healthy food, a massage and more, at the Maine Yogafest (July 10-12); join artists and art lovers in Mill Creek Park (August 8) for the 36th annual Art in the Park or, a few weeks later, head to Congress Street (August 22) for the 50th annual Sidewalk Art Festival.


Generations ago, Kennebunkport was a shipbuilding and fishing village. It has since grown into a picturesque summer hamlet, complete with ice cream shops, art galleries and grand mansions. But it’s still a salt-of-the-earth, hard-working village at heart, with an active marina, squawking seagulls and catch-of-the-day restaurants. One of Kennebunkport’s main roads is named Ocean Avenue and its town center is called Dock Square, additional reminders that this is truly a place of the sea.

Where to stay: One part sleep-over camp, three parts sophisticated resort, Hidden Pond aims to relax and reinvigorate couples and families alike. Initially designed as a modern neighborhood, a number of one-bedroom bungalows and two-bedroom cottages dot the gorgeous grounds—60 acres in all—and each home-away-from-home is unique, yet equally inviting, with unexpected pleasures like a screened-in porch and outdoor shower. A roster of adventures greets each day, from a guided hike to a kids in the kitchen class. If all that fun is too taxing, retreat to the Tree Spa, where stresses are defeated by a hard-to-choose-just-one selection of healing and restorative treatments. At day’s end, savor a dinner at Earth, with its nature-inspired setting and refined menu highlighting what’s available from the site’s organic gardens and local purveyors. Insider’s tip: Hidden Pond is part of the Kennebunkport Resort Collection—with several distinctive, spoil-you-rotten retreats, there’s one to match every vacation style.

What to do: Stroll in the sand along the unspoiled beaches; take a lovely drive around Ocean Avenue, and see if you can spot Walker’s Point—President George H.W. Bush’s summer home—from among the mansions. Golf at one of the many (many!) area golf courses; join Rugosa Lobster Tours and get hands-on lobstering experience on the Kennebunk River. Meander along the mile-long Marginal Way in nearby Ogunquit, one of New England’s only public, paved shoreline footpaths, with sweeping salty-air Atlantic views; and end a fun-filled day with a sunset cruise with Kennebunkport Coastal Boat Tours.

Where to shop: After browsing the many antique stores and souvenir shops, direct the car 20 miles south to York to buy Wild Maine Blueberry Jam directly from the source at the flagship store for Stonewall Kitchen. Bargain-hunters will continue a bit farther south, drawn to the deals at the Kittery Premium Outlets, with stores like Crate and Barrel and Lululemon Athletica. While in Kittery, visit the headquarters of The Clean Bedroom to test-drive (or test-nap) a premier selection of all-natural and organic mattresses in the company’s sleep showroom.

Where to eat: Enjoy a cup of coffee, a scone and a friendly chat with locals at Seed & Bean in sister-city Kennebunk. For lunch, combine award-winning fried seafood with great people-watching at The Clam Shack; then dress to the nines for an elegant, five-star dinner at Kennebunk’s The White Barn Inn, where ever-changing entrées might include steamed Maine lobster nestled on a bed of homemade fettuccine with carrot, ginger, snow peas and cognac coral butter sauce. And, for dessert, pick up a hand-made Maine blueberry pie from Pie in the Sky Bakery in nearby Cape Neddick.

Not-to-miss summer 2015 events: The Kennebunkport Festival (June 8-13) invites one and all to revel in the creations of Maine chefs, wine purveyors, beer makers, artists, gallery owners and musicians with cooking demos, wine-and-food pairings, music and more. And catch Sally Struthers at the Ogunquit Playhouse in the musical comedy, “Nice Work If You Can Get It” (July 22–August 15).


• Fly into Logan Airport (Boston) or Portland International Jetport (Portland, ME).
• Rent a car for ease in getting around, and for the pure pleasure of riding along coastal Route 1A.
• Don’t expect most locals to talk with a thick Maine accent.
• Take a day trip from Portland north to Freeport or south to Old Orchard Beach (or even Boston) aboard the Amtrak Downeaster.
• In addition to Maine lobster and wild Maine blueberries, be sure to sample Maine’s other delicacies, like maple syrup, whoopie pies and Moxie soda.

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