Kennebunkport, a Historic Seaside Retreat

Kennebunkport, a Historic Seaside Retreat


Kennebunkport Hotels are opening up July 1!

Check with the hotels, restaurants and activities  below for more information.

 Andrea McHugh

With its captivating coastline and quintessential New England charm, Kennebunkport in southern Maine has long been a summertime playground for travelers far and wide. Quaint buildings dating back to the late 18th and early 19th century add to the town’s Rockwellian charm, most especially in the Kennebunkport Historic District nestled in the village center. Visitors with an appreciation for rich history combined with an eye for authentic early American architecture will especially be drawn to this unique coastal community.

Though Kennebunkport was first incorporated as Cape Porpoise (or Cape Porpus) in 1653, the land was first home to Native Americans. Due to hostility between the native population and the settlers over the next 25 years, the area was considered “depopulated,” then repopulated, by Europeans in early 1700s with fishing, farming and shipbuilding rising as dominating trades. The town was renamed “Kennebunkport” in 1821 (to the Abenaki Indians, “Kennebunk” meant “the long cut bank," which historians conclude refers to the bank behind Kennebunk Beach.) The town emerged into a popular summer colony as early as the 1870s, with hotels and recreational accoutrements luring city dwellers to bask in the refreshing Maine seawater.

Today, Kennebunkport maintains its late 19th century charm as the authentic coastal village continues to invite visitors year-round, though most especially in the warm summer months.

Summer home and refuge to the two Bush Presidents and their families, Kennebunkport has long been a haven from the outside world

Where to Stay

Perhaps no inn better celebrates Kennebunkport’s shipbuilding legacy than the Captain Lord Mansion. Once the home of sea captain turned wealthy shipbuilder Nathanial Lord, this bed and breakfast (the only AAA Four Diamond rated B and B in town) includes 21 guest rooms amongst the three-story main home, the smaller (and more budget-friendly) Captain’s Garden House and the newest accommodation, the 1200-square foot executive suite dubbed “The Loft”. Federal period architectural details and furnishings can be found throughout while the elegantly appointed, individually designed rooms make you feel like you’re one of the Captain’s personal guests in this lush home which remained in the Lord family for more than 150 years. Look no further than innkeepers Rick Litchfield and Bev Davis for both top notch hospitality and sage advice when it comes to must-see attractions and the best lobster roll in town — they’ve been at helm here for more than three decades.

Those with a green thumb combined with a appreciation for history will want to stroll through Ganny’s Garden, a flowering tribute to one of Kennebunkport’s most famous and dearly missed summer residents, Barbara Bush, located on Trust’s River Green located just steps from the inn.

Nestled in the heart of Dock Square, the Kennebunkport Inn can trace it’s history back more than two centuries. For the majority of the 1800s, the home that stood there belonged to generations of the affluent Perkins family. At the turn of the century, Burleigh S. Thompson (remember this name), a wealth sea merchant, commissioned a grand Federal-style home built there, and by the late 1920s, new owners became the first to turn the home into an inn, adding a cocktail lounge and dining room to the 10 guest rooms in the main building (in addition to 26 rooms in the annex) during its first renovation (the room rate then was just $3 a night!). About 25 years later, the owners built shops on the property along Spring Street and in 2001, the owners guests have come to know and love today, Debra Lennon and Thomas Nill, claim the helm of the Kennebunkport Inn. The couple redecorated the guest rooms and common areas “guided by Kennebunkport’s colorful history as a shipbuilding and fishing village, as well as the 1899 home’s original Federal-style architecture.” Classic luxury meets modern flair throughout, but perhaps most especially at The Burleigh (sound familiar?), the cocktail lounge and restaurant. Since opening in 2017, The Burleigh has become the the hot social spot in town with a popular happy hour and menu best described as comfort food meets contemporary coastal cuisine.

For a memorable stay just outside of the village, the Captain Fairfield Inn offers a distinct tranquility as the branches of its centuries old elm and maple trees sway in the breeze off the Kennebunk River just a block away. Built in 1813 by Captain James Fairfield for life with his new wife, this home retains its authenticity with early Federal period architecture throughout as evidenced by wide pine floors (with a mildly charming creek) and detailed moldings. Just a five minute to shops and restaurants, you’ll feel like a local staying in this quiet neighborhood peppered with old sea captain’s homes. The 9-room inn is owned by Lark Hotels, known for boutique properties that blend history with chic, bold design. Insider’s tip: don’t sleep in too late as you won’t want to miss the variety of small plates at breakfast — or the warm afternoon cookies.

Where to Dine

The juxtaposition of rustic and refined is epitomized at The White Barn Inn Restaurant. Partially housed inside a restored barn more than 150 years old, many consider this renowned restaurant, now in its 45th year, the best you’ll find between Boston and the Canadian border (it has both AAA Five Diamond and Forbes Five Star endorsement to back the claim up). Visits to this culinary gem will seldom be the same as the menu, with a focus on contemporary New England cuisine (note: not an oxymoron), changes weekly. Gourmands should opt for Chef Matthew Padilla’s indulgent multi-course tasting menu. Though the restaurant is part of a luxury boutique hotel and spa, the restaurant is open to the public and well worth the visit.

When you’re ready to leave white table cloth dining behind, head to Mabel’s Lobster Claw, home to what might be the best traditional Maine shore dinner — a feast complete with New England clam chowder, native steamed clams and of course, a whole Maine lobster. Just a mile from Dock Square and open April through October, this longtime culinary staple for more than 60 years always delivers (and is usually the best lobster bargain in town).

Outside of the center of town in the quaint village of Cape Porpoise you’ll find Nunan’s Lobster Hut. Its menu is purposely limited to let its legendary lobster take center stage while the floor to exposed beam ceiling nautical decor (think: buoys, nets and traps) adds a campy flair. Don a bib, set aside your bag of potato chips, roll and pickles and slide your melted butter to a designated dipping area. If your appetite allows, save room for the ultra-creamy clam chowder or slice of homemade Maine blueberry pie.  

What to do and See

Who knew little Kennebunkport was home to the country’s largest and oldest museum of mass transit? It’s true; The Seashore Trolley Museum features vehicles from nearly all major cities in the U.S. — and some cities worldwide — that have streetcar systems in the form of more 200 than trolleys, trams, trains and buses. This isn’t a “behind the red rope” style museum, so be prepared to climb aboard a number of streetcars. Don’t miss the (quite apropos) ride aboard a turn of the century trolley. It’s a delightful way to not only see exhibits but the workshops dedicated to trolley car restorations as well (done by volunteers). You’re likely to bump into a one-time conductor or engineer here while learning more about the history of this mode of transportation that played a vital role in American history, ingenuity and the modern commute.

Kennebunkport has long been known as the summertime respite of the Bush family, where their oceanfront compound served as the Summer White House of the late George H. W. Bush. Perched on the tip of a peninsula known as Walker’s Point, the 41st President of the United States hosted heads of state at his Kennebunkport retreat including Margaret Thatcher and Mikhail Gorbachev. Today, the First Families Kennebunkport Museum, at White Columns, showcases two centuries of local and presidential history. Operated by the Kennebunkport Historical Society, guided tours tell the tales of the town’s prominent shipbuilders to its most famous summer residents. History buffs should make time for the 90-minute film about the late president and his family while architecture aficionados will revel in the guided tour of the 1853 Greek Revival home that during the village’s shipbuilding heyday, belonged to Charles and Celia Perkins. The affluent couple’s original furnishings, right down to the French wallpaper, is a walk through history.


There’s a palpable excitement when the History Channel’s “American Pickers” return to Maine, a state known for extraordinary antiquing. In Arundel (just a short drive from Kennebunkport’s village center), you’ll find what locals have dubbed “Antiques Alley” due to its alluring assortment antique shops. Conglomerates like Arundel Antique Village and Antiques USA feature hundreds of dealers under one roof teeming with thousands of treasures from eclectic collectibles, jewelry and china to mid-century modern furnishings. But it might just be the Arundel Flea Market, considered one of if not the best flea in the state. Though open year round, this roadside swap meet shines brightest in the summertime when hundreds flock in search of their undiscovered finds. Here’s the thing: this is Maine, and there’s some serious antiquing here in Vacationland. So, if you’re a casual browser, by all means, stroll in anytime before 5 p.m., but if you’re a serious treasure hunter, you’ll want to arrive before the sun rises. Seriously. (Pro tip: make your own coffee because the local coffee shops may not even be open yet.) All in all, you’ll find upwards of 50 antique shops along the 30-mile stretch between Arundel and Kittery, so if antiquing is high on your Maine getaway, plan accordingly.

Last but not least

The Beaches

There is no mistake about it, Maine’s beaches are not fine, sandy beaches but they have vibe all their own that is not to be missed.  You’ll need a sticker or beach pass to park which you can get at Town Hall.  Gooch’s Beach, Middle Beach and Mother’s Beach are perfect for sunning, playing or rock and sand dollar collecting.

The Wedding Cake House

One of the best known architectural sites statewide (and rumored to be the most photographed in all of Maine) is in neighboring Kennebunk: the Wedding Cake House. Built in 1825 by shipbuilder George W. Bourne, the Federal-style home drips in ornate Gothic detail and stands out among the other one-time sea captain’s homes along tony Sumer Street. The home is not open to the public and sadly is slipping into disrepair, so now is the time to see this architectural gem as its future is uncertain.

Kennebunkport Walking Tours

There are a few guided walking tours offered, one at Brick Store MuseumThe Kennebunkport Historical Society and a self guided tour offered by Museum in the Streets, which is heritage tour by the National Park Services and is free.  Go here to download the guide and enjoy the walk at your own pace.

Andrea McHugh

Andrea E. McHugh is a media manager, content creator and freelance writer specializing in lifestyle topics including travel, fashion and beauty, homes, weddings and wellness. She’s a regular style correspondent for The Rhode Show on WPRI (CBS) Providence and contributing writer for ArtisansList.com.

She served as an editor for Newport Life and Newport Weddings magazines and her work has appeared in Family Circle, the Hartford Courant, Classic Boat Magazine, Baltimore Magazine, Cape Cod Home, Daily Candy, Design Sponge, Northern Virginia Sun Gazette newspapers, Ocean Avenue, New England Gala Weddings, Providence Monthly and additional regional, national and international print and digital publications.

This post was first published on May 6, 2019

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