Kennebunkport, a classic coastal village nestled along Maine's southern shoreline, effortlessly blends New England charm, maritime history, and boutique sophistication. This past summer, I took my grandma on a delightful two-day escape, with Kennebunkport topping our must-visit list. It proved the perfect destination for blending laid-back leisure with gentle adventure—ideal for multigenerational travel.

Morning in Kennebunkport: Downtown Wandering

Our day began in Dock Square, the picturesque heart of Kennebunkport. Here, local boutiques, artisan shops, and charming cafés line the quaint streets, framed by historic architecture and blooming flower boxes. It felt as if we'd stepped onto a vintage postcard, with every corner offering something new to explore.

We started our morning at Sea Love, a delightful shop specializing in artisan candles and locally harvested sea salt. The inviting aroma drew us in immediately. Beyond candles, Sea Love offers hands-on candle-making workshops, allowing visitors to craft their own scented souvenirs—a perfect girls' trip activity!

Next, we strolled leisurely along the storefronts, each shop beckoning us with unique offerings. The standout, however, was Maine-ly Drizzle, a charming boutique featuring locally-made olive oils and balsamic vinegars. The rich aromas and incredible variety made this a sensory haven—I could have easily purchased everything! With flavors ranging from blueberry-infused balsamic to basil-infused olive oils, it's an ideal spot for thoughtful gifts or gourmet kitchen treasures.

Lunch by the Water: Boathouse & The Clam Shack

As midday approached, we were ready to soak up Kennebunkport’s waterfront ambiance over a light lunch. We chose The Boathouse, known for its dockside views and fresh, coastal-inspired menu. Settling onto their outdoor patio, we indulged in perfectly cooked fish sandwiches accompanied by crisp, salty fries. The setting was as satisfying as the meal itself, with boats gently bobbing in the harbor and seabirds wheeling above.

Though The Boathouse was wonderful, another iconic lunch destination, highly recommended for lobster lovers, is The Clam Shack. Located at the bridge entrance to Dock Square, The Clam Shack has repeatedly earned accolades—including being voted America's best lobster roll by Food & Wine magazine. Their lobster roll is celebrated for simplicity: freshly picked lobster piled onto a toasted bun, lightly brushed with butter. It's a Kennebunkport staple you simply can't miss.

Afternoon Explorations: History & Sweet Treats

PosFirst settled in the early 1600s, the village thrived as a fishing outpost before evolving into one of New England’s busiest ship-building hubs by the 19th century. Many of the beautifully preserved sea-captain mansions you see along Ocean Avenue and in the River Green district were financed by schooners and clipper ships launched from local yards—vessels that once carried Maine timber and ice to ports as far as Havana and Liverpool. Today, plaques and small maritime exhibits scattered around Dock Square quietly nod to that golden era, while the town’s working harbor still shelters lobster boats that keep Kennebunkport’s seafaring heartbeat alive.

No Kennebunkport day is complete without a proper ice-cream stop. Rococo Artisan Ice Cream (Dock Square) rotates inventive, globally inspired flavors—think Maine blueberry–chamomile or sweet-avocado-lime—made with local milk and fruit. Ben & Jerry’s on Western Avenue delivers tried-and-true classics in a nostalgic New England storefront (perfect if you’re traveling with kids). For something playful, Satellite Donuts & Ice Cream pairs warm mini-donuts, fried to order, with small-batch ice cream—a sweet finale that bridges old-fashioned charm and modern creativity.

Evening Wind-Down: Beaches and Sunsets

Just a five-minute drive from Dock Square, Gooch’s stretches for nearly a mile along Kennebunk’s Atlantic Avenue—broad, flat, and perfect for all ages. Metered parking runs the length of the seawall (arrive before 10 a.m. in summer to guarantee a spot), and two dune paths provide wheelchair-friendly beach-mat access. At low tide, tidal pools shimmer with tiny crabs and periwinkles—guaranteed entertainment for kids or curious grandparents. Surfers favour the eastern end near the jetties, while sunrise walkers stake out the western curve for panoramic Atlantic views. Restrooms and seasonal lifeguards make it an easy half-day outing; pack a blanket, grab iced coffees at Mornings in Paris on the way, and linger until the late-afternoon light turns the sand honey-gold.

]If you have energy for one more coastal ramble, drive (or cycle) the short loop to Ocean Avenue and pick up the Parsons Way trail opposite St. Ann’s stone church. This two-mile, mostly flat path traces the rocky shoreline past spruce-capped promontories, tidal inlets, and the “Blowing Cave,” where waves funnel through a seaside cleft with a theatrical whoosh. Benches along the route frame postcard views of Walker’s Point—the Bush family’s summer compound—making it a gentle, scenic outing for travellers of any pace. Bring a light jacket; late-day sea breezes can be brisk even in midsummer, and the sunset from this vantage is worth every extra layer.

Capturing Timeless Memories

Our day in Kennebunkport was a gentle reminder of the beauty found in slowing down and savoring the small moments—especially in good company. Whether it's discovering local artisans, savoring fresh seafood, or simply sharing quiet moments by the sea, Kennebunkport provides an authentic and enriching experience that resonates across generations.

Ready to create your own memories? Start planning your visit to Kennebunkport, and experience firsthand the coastal charm that makes this seaside village a timeless destination.

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