Kennebunkport is a small coastal town, but it has a big personality. Located along Maine’s southern shore, it’s known for its charming streets and sandy beaches.
There’s history and seaside fun. People come for lobster rolls, ocean views, and that sense of stepping into a classic New England atmosphere.
The town’s roots stretch back to shipbuilding and fishing. You’ll still notice that heritage in the old captain’s homes and the working docks.
These days, Kennebunkport mixes its past with cozy inns and waterfront resorts. There are plenty of ways to enjoy the outdoors, too.
You can stroll through Dock Square. Or paddle on the river. Sometimes, just sitting by the shore is enough…
In this article, I’ll explore 10 experiences that really show off the town’s character. Beaches, boat tours, ghost stories, and, of course, local seafood…
You’ll find tips on where to stay, eat, and explore. It’s meant to help you enjoy Kennebunkport like a local, but with a few surprises along the way.
So, let’s get started!
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Keep in mind: Our articles may contain errors, despite our best efforts. So, do thorough research before deciding on a travel destination.
1. Dock Square
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Dock Square is the energetic center of Kennebunkport. It’s an easy place to stroll, window-shop, and grab a snack. You’ll find art galleries, local craft stores, and friendly cafés lining the streets.
Many buildings here date back to the town’s shipbuilding days, when Kennebunkport was known for schooners and trade. You can look for small plaques on storefronts that share bits of history.
If you like local flavor, try a whoopie pie or saltwater taffy while you walk. Dock Square also hosts events in warmer months, so you might catch music or a small festival. It’s a comfortable place to start your visit and get a feel of the town.
For a stay nearby, consider The Kennebunkport Inn right on the square, or The Boathouse Waterfront Hotel, which overlooks the harbor. Both put you right in the middle of the action.
Early evening is a nice time to visit, when the lights come on, and the harbor breeze cools the air. Bring a light jacket, and take your time exploring the small lanes and side streets that lead to the river.
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2. Ocean Avenue
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Ocean Avenue is a scenic road that follows the shoreline from Dock Square toward the Atlantic. You can drive slowly or park and walk sections for coastal views, sea air, and the sound of waves.
Along the way, you’ll see rocky outcrops, old shingle-style homes, and small coves. Local fishermen still work these waters, and you might see lobster buoys offshore. The road also passes by St. Ann’s Episcopal Church, a stone chapel from the early 1900s on a bluff above the ocean.
It’s a peaceful place to pause and look out at the horizon. Bring a camera; sunrise and late afternoon light are especially nice on the water.
If you want to stay close, the Nonantum Resort is near the river end of Ocean Avenue and offers access to waterfront paths.
Another option is the Kennebunkport Captain’s Collection, a group of historic inns within a short ride.
Keep an eye out for tidal changes. Low tide reveals more rocks and tidepools, while high tide brings the waves closer to the road.
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3. Walker’s Point Estate
(Walker’s Point Estate, Kennebunkport, Maine, USA – Photo by Rusty Watson)
Walker’s Point is famous as the summer home of the Bush family. While the property is private, you can view the compound from the roadside pull-offs along Ocean Avenue.
The point has a rugged, classic Maine look: rocky ledges, spruces, and waves rolling in from the Atlantic. The home’s location reflects Kennebunkport’s long connection to the sea and its history as a place where families have returned for generations.
Many visitors enjoy the quiet moment of looking out at the water and imagining coastal life over the last century. Bring binoculars if you like seeing seabirds or boats in the distance.
There’s often a breeze, so a light layer helps. After your stop, you can continue along the shore for more views or circle back to town.
Nearby stays include The Colony Hotel along the coast and The Breakwater Inn & Spa on the river, both within a short drive.
A suggestion: Respect the privacy of the area and use designated viewing spots so everyone can enjoy the scenery safely and comfortably.
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4. Goose Rocks Beach
Goose Rocks Beach is a wide and sandy stretch north of Kennebunkport. It’s a calm place for walking, wading, and building sandcastles. At low tide, the beach opens up and tidepools appear, which are fun for kids to explore.
Offshore, you can see timber “goose rocks” that gave the beach its name. The area has long been a summer spot for families, and you’ll feel that relaxed vibe as you settle in for a day by the water.
You can pack a simple picnic, sunscreen, and a kite if there’s a breeze. The shoreline here is gentle, and the sound of the waves is soft.
If you want to stay close, The Tides Beach Club is right across from the sand and offers easy beach access. Hidden Pond, a forested resort a short drive away, is another good option if you prefer a nature setting with cottages.
Parking can be limited in peak season, so try to arrive early or plan for a short walk.
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5. Sailing or Lobster Boat Tour
(Kennebunkport, Maine, USA – Photo by Rich Martello)
Getting on the water gives you a true feel for Kennebunkport. Sailing tours glide along the coast, offering views of lighthouses, rocky shores, and seabirds.
Lobster boat trips are hands-on and show how traps are pulled, measured, and re-baited. You’ll learn about the lobster fishery and why it matters to Maine communities. Some captains share stories from years at sea, including how weather and tides shape their daily work.
Dress in layers as it can be cooler on the water even on warm days. Keep your camera ready for seals or porpoises if you’re lucky. Tours usually last one to two hours, making them easy to fit into your day.
Around the harbor, you’ll find operators offering both styles: sailing for quiet and scenery, lobster boats for learning and action.
If you want to stay by the docks, The Boathouse Waterfront Hotel is steps from many departures. The Nonantum Resort also hosts boat pickups in season. Book ahead in summer, and check conditions on windy days.
6. Historic Walking Tour
A guided historic walk will help you see the town in a new way. You’ll hear about shipbuilding, sea trade, and how Kennebunkport grew from a small river settlement to a coastal hub.
Many tours point out Federal-era homes and former captains’ houses, showing details like fanlights, old anchors, and maritime symbols. You may stop by the Kennebunkport Historical Society or pass sites like White Columns, a historic home museum.
Stories bring the past to life, like how storms changed the shoreline or how local craftsmen built vessels by hand.
Tip: Wear comfortable shoes. The route is flat, but you’ll want to walk side streets. Self-guided maps are also available if you prefer to go at your own pace. After the tour, you can get a cup of chowder or a coffee in Dock Square.
If you want to stay in a historic setting, the Kennebunkport Captain’s Collection offers restored inns with period charm. Another option is The Colony Hotel, a classic coastal property that shows the town’s heritage.
7. Ghost Tour
Ghost tours mix local lore with evening walks through quiet lanes and waterfront paths. Guides share stories about old sea captains, stormy nights, and houses that may hold a secret or two.
Whether you believe in ghosts or not, it’s a fun way to learn bits of history that don’t always make the guidebooks. You’ll hear how shipwrecks, long winters, and tight-knit communities shaped legends over time.
Bring a small flashlight and wear good shoes as sidewalks can be uneven. Tours are usually family-friendly but may include spooky tales, so think about what’s right for your group. Afterward, you can warm up with hot cocoa or a late dinner in town.
Staying nearby makes it easy to join a tour and head back without driving: The Kennebunkport Inn and The Boathouse Waterfront Hotel are both close to meeting points.
If you prefer something quieter, The Breakwater Inn & Spa by the river offers a calm base. And enjoy the storytelling…
8. Enjoying Fresh Lobster and Seafood
Seafood is a big part of life in Kennebunkport. Try a lobster roll on a toasted bun, a cup of clam chowder, or fried clams with tartar sauce. Places like The Clam Shack near the bridge are known for simple and tasty bites.
Sit by the water and watch boats pass while you eat. Many restaurants source locally, so the menu often changes with the season. If you like a sit-down meal, check out spots such as Mabel’s Lobster Claw or Alisson’s in Dock Square.
You can ask about the day’s catch and how it was prepared. You’ll learn the difference between soft-shell and hard-shell lobster or how oysters are farmed nearby.
For convenience, you can stay within walking distance: The Kennebunkport Inn and The Boathouse Waterfront Hotel make it easy to explore dining on foot.
If you want a resort feel, The Colony Hotel has on-site dining and ocean views. Tip: Aim for early lunch or dinner in peak season to avoid lines.
Read also: 12 Must-Try Foods in New England for Your Bucket List
9. Kayaking or Paddleboarding on the Kennebunk River
The Kennebunk River offers calm water and easy paddling for all levels. Rent a kayak or paddleboard and head upstream for quiet marsh views and birdwatching, or downstream toward the harbor for more activity.
You’ll see working docks, small boats, and maybe a harbor seal popping up to look around. The river is tidal, so check the tide chart: currents can change your effort level.
Many visitors enjoy a two-hour paddle, which allows time to stop, float, and take photos. Local outfitters provide gear, life vests, and tips on routes. Tip: Wear sun protection and bring water, even on cooler days.
If you want to stay close to launch points, The Nonantum Resort sits right by the river and often partners with activity providers. The Breakwater Inn & Spa also offers convenient access.
It’s a simple way to experience the town from a new angle, moving at your own pace and hearing the sounds of gulls and distant waves as you explore…
10. The Seashore Trolley Museum
The Seashore Trolley Museum is a short drive from Kennebunkport and is known for its collection of historic streetcars and transit vehicles. You can ride a restored trolley on a wooded track, which feels like going back in time.
Exhibits explain how streetcars shaped towns and daily life before buses and cars took over. Kids enjoy climbing aboard and seeing how conductors worked.
The museum started in the late 1930s to save trolleys that were being retired, and it has grown through donations and volunteer efforts. Plan about two hours for your visit, including the ride and display halls.
For places to stay nearby, consider The Rhumb Line Resort for a family-friendly base or Hidden Pond if you prefer a nature retreat with cottages.
The museum goes well with a morning in town. You can visit and then return to Dock Square for lunch. It’s a good way to learn about New England transportation history.
Until next time…