Our Favorite Places: The Perfect Summer Weekend in Kennebunkport, Maine

With spring upon us, summer can’t be far behind.  Our thoughts are turning to summer vacation: lazy days at the beach, boat rides, outdoor happy hour cocktails, and evening fire pits complete with s’mores.  Before we had an office in Kennebunkport, a visit to Maine was an annual summer pilgrimage for CIRE president, Eric Hrubant.  And CIRE COO Amy Brueckner lives in the area year-round.  Read on for some of their favorite ways to spend a perfect weekend in Vacationland, complete with multiple lobster rolls, of course.  And if this has you craving a luxury vacation to New England, call the travel experts at CIRE to help plan the perfect trip!


Summertime in Maine is beach season and there are some gorgeous beaches in Kennebunkport and neighboring Kennebunk.  Goose Rocks is our top beach pick if you’re staying nearby (see our “STAY” recommendations below).  However, if you’re not staying at a nearby hotel, parking at Goose Rocks is highly regulated (and kind of a nightmare).  Just across the river in Kennebunk, there are three more great beaches (with more abundant paid parking): Gooch’s Beach, Middle Beach and Mother’s Beach.  Gooch’s is a huge sandy beach at low tide, considerably smaller at high tide and popular with surfers.  Middle Beach is rockier and quieter.  And finally, Mother’s Beach is a great option for the kiddos since it’s smaller, sandy, and on a more protected cove boasting a sizable playground.  The entire stretch of these three beaches is just a mile long, so take a walk or a drive and pick your favorite.

There are plenty of non-beach options, too.  Dock Square, Kennebunkport’s town center, is loaded with charming shops and restaurants.  Some of our favorite stores include Minka, Daytrip Society, The Candyman, Good Earth Pottery and Maine Art Hill, which is just on the other side of the bridge.  Speaking of the bridge, a photo in front of the iconic “Welcome to Kennebunkport” sign is a must.  Then cross the street and get another photo in front of the “Kennebunk Welcomes You” sign!  (The dividing line of Kennebunk and Kennebunkport is the Kennebunk River.)

Two other shops that CIRE COO and Kennebunk resident, Amy includes on tours when friends and family come to visit are Snug Harbor Farm and Farm + Table.  “Snug Harbor is a charming shop, greenhouse and farm complete with miniature ponies and numerous fancy birds like peacocks and faverolles (feather-footed chickens).  I love strolling the grounds and greenhouses to get inspired for my own garden.  I usually leave there with a new succulent or plant on every visit.  Inside, their delightful store has everything from jewelry to textiles to lotions, potions, soaps, and, yes, more plants!”  Snug Harbor is only a mile from the Dock Square shopping area.  Further afield, but still in Kennebunkport in the fishing village of Cape Porpoise, is Farm + Table.  “Liz and Bruce are the owners and curators of this fabulous shop.  My absolute favorite in the area.  Every friend I bring leaves with something special.  It’s a true gem.”  After a visit to Farm + Table, follow Pier Road all the way to the end for a view of the lighthouse, great photo ops, and a real working lobster pier.

And of course, in addition to beaching and shopping, there are lobster boat tours, whale watching tours, fishing charters, sailing excursions, bike and kayak rentals, and more.  Two activities we recommend for first timers is Rugosa Lobster Tours and the Cape Porpoise Lighthouse Tour with Coastal Maine Kayak.


Hidden Pond is a luxury resort located in a woodsy, tranquil part of Kennebunkport.  Amy recalls…  “My husband and I stayed at Hidden Pond back in 2012.  That weekend getaway was a big reason we fell in love with, and eventually moved to, the Kennebunks.”  The resort is a collection of charming bungalows, cottages and tree-top lodges ranging in size from studios to 2-bedrooms.  Each dwelling has a screened-in porch, working fireplace, and all the New England charm you can handle.  Breakfast is delivered to your cottage each morning: A thermos of hot coffee, fresh pastries and fruit, and there’s OJ and yogurt in the fridge.  A spa, two pools, a top-notch restaurant, and nightly campfires complete with s’mores are just a few of the selling points.  Complementary loaner bikes will help you scoot around the property.  Also, it’s less than a 2-mile ride to Goose Rocks beach where you can use the umbrellas and chairs at Hidden Pond’s sister property, The Tides Beach Club.  Parking nightmare averted!


After the beach (or your daytime activity of choice), a drive along Ocean Avenue is a must.  Stop at Walker’s Point to see if you can spot George (known locally as “43”), Laura, Jenna or any of the Bush family at their summer retreat.  (Hint: If the Texas flag is raised on the flagpole, the Bushes are in town.)  A stone’s throw down the road, stop at the Cape Arundel Inn and the elegant Ocean restaurant for a sundowner.  The bar inside is small, but the real winning spot is a seat on their front porch over-looking the craggy coast and the Atlantic Ocean.  This is the place for an upscale cocktail and quiet conversation.  For a livelier happy hour atmosphere, head back to Dock Square and visit The Spirit Restaurant.  The Spirit is a former seafaring vessel, The Spirit of Massachusetts, that was retired and set permanent anchor in the Kennebunk River.  You’re right in the middle of the action on The Spirit, with fabulous water views as well as the perfect perch to check out what’s going on in town.  Order your favorite cocktail from genial bartenders Jeff or Mike, and enjoy some live music and a cool breeze.


Earth, the restaurant at Hidden Pond, is a top pick in the area and not to be missed.  We recommend reserving one of the private dining sheds for a romantic dinner.Wandby Landing Off-property, there are two new-comers worth checking out: Wandby Landing and Via Sophia by the Sea.  Wandby Landing prides itself on using only the freshest local ingredients, so the menu changes regularly.  The standouts are the vibrant salads (that look more like a gorgeous flower arrangement or work of art than an appetizer) and the house made pasta.  The other new kid on the Maine restaurant scene is Via Sophia by the Sea, an extension of Via Sophia restaurant in Washington, DC.  If you already had a lobster roll at lunch but still haven’t had enough Maine lobster, try the Lobster Agnolotti.  Trust us!


Yes, lobster rolls get their own category…it’s Maine, after all! “When my sister comes to visit, she eats at least one lobster roll per day. And anytime we take her to a place she hasn’t been before she orders their signature lobster roll,” Amy shares. Virtually every restaurant in town has one on the menu. Mayo, butter, long bun, round bun…each lobster roll is unique. Try as many as you can and let us know your favorite! Our top two are definitely The Clam Shack and the Cape Pier Chowder House. Also, Eric wanted us to tell you that his favorite New England Clam Chowder is at The Pilot House. We’ll need another article to debate the top chowders in the area.


Maine is always a good idea.  And a visit to The Kennebunks in the summer is a fantastic idea.  If you want to plan a romantic weekend by the sea or a weeklong family vacation, the team at CIRE is here to help with their travel expertise and insider knowledge.  Maine is also great for a fall road trip (ATTENTION: LEAF PEEPERS) and winter, too.  In fact, one of the most popular articles on CIREtravel.com is this one we wrote about the perfect winter weekend in Kennebunkport.  Whatever the season, wherever the destination, the expert team of professional travel advisors at CIRE are ready to help you plan that perfect trip.

CIRE Travel is a full-service travel agency headquartered in New York, NY.  Our expert team supports clients across the country and around the world.

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