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Kennebunkport, Maine, is the place where every cobblestone sidewalk and weathered dock feels like stepping into a storybook seaside fantasy.
Here, time slows down just enough to savour the small-town magic: the way golden light hits the Atlantic Ocean at dusk, the thrill of discovering a hidden art gallery down an alley, the first bite of a still-warm blueberry pie from a farm stand. It’s where you’ll find yourself saying, “Wait, is this real?” at least once daily.
And the best part? Kennebunkport and Kennebunk (its equally charming neighbour) pack more adventures into one stretch of coastline than most states in 100 miles. From whale watching to lighthouse picnics, we’re about to unpack all the best things to do in Kennebunkport, Maine, starting right now.
But wait, what about Kennebunk? Just a quick drive away, Kennebunk shares the same stunning coastline but with its personality. Kennebunkport and Kennebunk (often called “The Kennebunks”) make up one of Maine’s most beloved vacation spots. Whether you’re here for sandy beaches, boutique shopping, or a taste of New England history, this guide covers you.
In this ultimate list of the best things to do in Kennebunkport, Maine, we’re diving into:
- Iconic spots (like Dock Square & Walker’s Point)
- Must-try food (lobster rolls, waterfront dining, and yes—ice cream!)
- Hidden gems (from lighthouses to scenic boat tours)
- Seasonal highlights (fall foliage, winter festivities, and summer fun)
Ready to explore? Let’s start with the heart of Kennebunkport!
The Heart of Kennebunkport: Dock Square & Ocean Avenue
1. Stroll and Shop in Historic Dock Square
Dock Square is where the action happens. This bustling waterfront hub is packed with:
- Quirky boutiques (think nautical decor and Maine-made crafts)
- Art galleries (local artists love this town!)
- Sweet treats (stop by Rococo Ice Cream for unique flavours like Maine Sea Salt Caramel)
Pro tip: Grab a coffee, wander the cobblestone sidewalks, and soak in the old-school New England vibes.
2. Drive or Walk Scenic Ocean Avenue
For knockout ocean views, Ocean Avenue is a must. This winding coastal road offers:
- Postcard-worthy sights of the Atlantic Ocean crashing against rocky shores
- A peek at Walker’s Point (the famous Bush family compound)
- A quick detour to St. Ann’s Episcopal Church, a tiny seaside chapel with dreamy views
Roll down the windows, feel the breeze, and snap pics—this is Maine’s most picturesque.
3. Indulge in Maine’s Culinary Delights
No trip to Kennebunkport is complete without eating your way through town. Must-tries:
- The Clam Shack – Tiny spot, HUGE lobster rolls (order them “naked” for maximum flavour).
- The Boathouse Restaurant – Waterfront dining with killer sunset views.
- Earth at Hidden Pond – Fancy farm-to-table in a cosy woodland setting.
- Dock Square ice cream – Because vacation calories don’t count.
Dock Square, Kennebunkport
Beaches & Water Adventures
4. Enjoy the Gorgeous Beaches of Kennebunkport
Kennebunkport’s shoreline is a work of art by nature, providing beaches that are anything from bustling playgrounds for families to private expanses of sand where the only things that can be heard are the cries of seagulls and the soothing crash of waves.
Gooch’s Beach is the classic summer spot, with its vast stretch of soft, golden sand and softly lapping surf that’s ideal for swimming. It’s a favourite with families due to its convenience and facilities, although be aware of parking permits in the height of summer. Get there early to get a good spot!
Mother’s Beach does not disappoint with its peaceful, shallow waters that make it perfect for tots: the nearby playground and picnic spots round out its popularity, making it a hassle-free option for parents.
Middle Beach provides a more sedate alternative, with low tide exposing interesting tide pools filled with sea creatures. It’s an excellent place for reflective strolls or simply basking in the ocean scenery without the masses.
Goose Rocks Beach is a secluded treasure running three miles along the shoreline. Its tranquil mood and soft sand make it ideal for long promenades, combing for shells, or relaxing with a novel. The absence of significant crowds here is like a kept secret.
Colony Beach is a small, rocky cove that seems like a million miles away from the more crowded areas. It’s perfect for those who love the untamed beauty of the Maine coastline, with tide pools to discover and lots of secluded nooks for contemplation.
Goose Rocks Beach
5. Embark on a Lobster Boat Tour
A lobster boat tour is essential for an authentic taste of Maine’s maritime culture. Rugosa Lobster Tour offers a hands-on experience where you’ll learn the art of lobstering from seasoned fishermen.
- Haul traps and see how lobsters are caught, measured, and released (or kept for dinner!).
- Spot seals lounging on the rocks as you cruise the Kennebunk River, with the captain sharing tales of life at sea.
- Take in Kennebunkport’s sights from the water, including grand waterfront homes and working fishing boats.
It’s an engaging, educational adventure that’s as fun for kids as adults.
6. Go Whale Watching
The waters off Kennebunkport are a playground for marine giants, and First Chance Whale Watch offers unforgettable excursions to see them up close.
- Humpback whales often breach dramatically, their massive tails slapping the water.
- Finback whales, the second-largest species on Earth, glide gracefully through the waves.
- Dolphins and porpoises frequently join the show, darting alongside the boat.
Dress in layers; the ocean breeze can be chilly, and bring your camera for once-in-a-lifetime shots.
Atlantic view from Kennebunkport
7. Explore the Kennebunk River by Kayak or Paddleboard
Paddling the Kennebunk River is one of the best ways to appreciate the area’s natural beauty.
- Rent a kayak or paddleboard and set off at your own pace, gliding past salt marshes and under historic bridges.
- Join a guided tour to discover hidden coves and learn about the local ecosystem from an expert.
- Watch for ospreys diving for fish and herons stalking the shallows.
The river’s calm waters make it suitable for all skill levels, and the perspective from the water is unbeatable.
8. Take a Scenic Schooner or Sunset Cruise
For pure romance and relaxation, set sail on a classic Maine schooner.
- Schooner Eleanor, a beautifully restored wooden vessel, offers daytime sails where you can help hoist the sails or simply lounge on deck.
- Pineapple Ketch specialises in sunset cruises, where the sky transforms into a canvas of pinks and oranges over the Atlantic Ocean.
Sip a local craft beer or wine as the wind fills the sails, the epitome of coastal bliss.
Kennebunk River
Beyond the Shore: History, Nature & Unique Attractions
9. Step Back in Time at the Seashore Trolley Museum
This charming museum is a delight for history buffs and families alike.
- Ride vintage trolleys through scenic woodlands, feeling the breeze as the antique cars clatter along the tracks.
- Explore exhibits showcasing the golden age of electric railways, with beautifully restored trolleys worldwide.
- Special events, like “Pumpkin Patch Trolley” in fall, add seasonal fun.
It’s a nostalgic journey that captivates visitors of all ages.
10. Discover the Quiet Charm of Cape Porpoise
This picturesque fishing village feels like a step back in time.
- Stroll the working harbour, where lobster boats unload their catch and gulls circle overhead.
- Admire Goat Island Lighthouse, a postcard-perfect beacon best viewed from Cape Pier or on a boat tour.
- Grab lunch at The Ramp, a no-frills spot serving fresh seafood with waterfront views.
Cape Porpoise’s unhurried pace is a refreshing contrast to busier parts of town.
Seashore Trolley Museum
11. Hike or Bike Rachel Carson National Wildlife Refuge
Named for the famed environmentalist, this refuge is a sanctuary for wildlife and visitors.
- Walk the Carson Trail, an easy 1-mile loop winding through salt marshes and woodlands.
- Birdwatchers will delight in spotting egrets, ospreys, and migratory species.
- Bike the quiet roads surrounding the refuge for more extended explorations.
The peaceful beauty here is a reminder of Maine’s untamed wilderness.
12. Explore Local Art Galleries
Kennebunkport’s vibrant arts scene reflects its coastal inspiration.
- Abacus Gallery: Step into a world of joyful color where Maine’s playful side shines through. Local artists fill the space with whimsical pottery shaped like sea creatures, bold paintings of crashing waves, and handcrafted jewelry incorporating sea glass and shells. The gallery feels like a celebration of coastal living; you might leave with a lobster-shaped serving platter or a watercolor that perfectly captures that golden Kennebunkport light.
- F-8 Gallery: The dramatic Maine coastline takes center stage through striking photography. Gorgeous oversized prints let you study every detail of wave-smoothed pebbles, misty lighthouse mornings, and the fiery oranges of autumn reflected in still harbors. It’s the next best thing to having your own private Maine vista.
Whether you’re a collector or browsing, these galleries offer a feast for the eyes.
New England, Pier dock
13. Stroll Parson’s Way Shore Walk: A Symphony of Sea and Stone
This breathtaking 2-mile coastal path is where Kennebunkport’s natural drama unfolds at every turn. Starting near Dock Square, the crushed shell trail winds past:
- Nature’s Theater: On your left, the Atlantic puts on an endless performance, waves explode against jagged granite outcrops, sending spray into the air while cormorants dive for fish. Explore tide pools glittering with sea stars and hermit crabs at low tide.
- Architectural Grandeur: To your right, peek through hedges at historic summer “cottages,” massive pebbled estates with wraparound porches where Gilded Age families once summered. The most famous view comes midway: Walker’s Point, the Bush family compound, sits regally on its rocky peninsula.
- Perfect Pauses: Strategically placed benches invite you to linger. Time your walk for sunrise (when pink light bathes the coast) or sunset (when the water turns molten gold). Bring binoculars, you might spot seals bobbing just offshore.
Kennebunkport Shore
14. Visit Historic Churches
Kennebunkport’s spiritual landmarks double as artistic and architectural wonders:
- St. Ann’s Episcopal Church: This 1887 seaside chapel is the stuff of fairy tales. Its stone walls and cedar pebbles blend into the coastline, while inside, sunlight filters through stained glass windows depicting nautical themes, fishing boats, lighthouses, and Christ walking on water. Sit in a pew to admire the hand-carved wooden ship model hanging from the ceiling, a tribute to Maine’s maritime heritage. The adjacent Ocean Lawn offers sublime picnic spots with harbor views.
- South Congregational Church: A textbook example of New England ecclesiastical architecture, its soaring white steeple has guided sailors since 1824. The simple elegance of polished wood pews and a massive pipe organ contrasts with the dramatic “Ascension” stained glass window behind the altar. Don’t miss the historic cemetery, where weathered headstones tell stories of sea captains and early settlers.
Even non-religious visitors find these spaces moving; the play of light through colored glass, the scent of old hymnals, and the profound quiet (broken only by distant gull cries) create unexpected serenity.
St. Ann’s Episcopal Church
V. The Kennebunks: Exploring Kennebunk & Lower Village
15. Discover Kennebunk’s Main Street & Lower Village
Just a short drive from Kennebunkport’s bustling Dock Square, Kennebunk’s Main Street and Lower Village offer a more laid-back, residential charm, think tree-lined streets, historic homes, and quaint storefronts that invite leisurely exploration.
- Boutique Hopping: Browse unique shops like H.B. Provisions, a rustic-chic general store stocked with Maine-made goods, or Daytrip Jr. for stylish kids’ clothing and toys.
- Dining with Local Flair: Stop by Mabel’s Lobster Claw for classic seafood in a cozy setting (a favorite of the Bush family!) or Rapid Ray’s for clam cake burger.
- Waterfront Strolls: Follow the Kennebunk River past charming marinas and under historic bridges, the perfect pre-dinner walk.
16. Enjoy Craft Brews at Local Breweries
Maine’s craft beer scene thrives in the Kennebunks, where breweries blend coastal vibes with creative flavors.
- Federal Jack’s Restaurant & Brewpub: The birthplace of Shipyard Brewing, this waterfront spot serves pub fare alongside seasonal brews like “Pumpkinhead” in fall or “Melonhead” in summer. Grab a seat on the deck for river views.
- Batson River Brewing & Distilling: A rustic-chic space offering small-batch bourbon and beers like the “Saltwater Hefeweizen,” perfect for sipping by the firepit.
- Kennebunkport Brewing Company: Known for quirky flavors (think blueberry ale or coffee stout), this tasting room is a fun stop after a day of exploring.
Pro Tip: Try a flight to sample local flavors. Each brewery has its own personality.
17. Go Bowling at Garden Street Bowl (Kennebunk)
For a dose of retro fun, head to Garden Street Bowl, where boutique bowling meets modern comfort.
- Luxury Lanes: Glow-in-the-dark pins, plush seating, and a full menu (loaded nachos, craft cocktails) make this anything but your average alley.
- Family-Friendly: Kids love the lively atmosphere, while adults appreciate the well-stocked bar.
- Late-Night Vibes: On weekends, DJs spin tunes for a party-like feel.
Kennebunkport Through the Seasons: Fall & Winter Magic
A. Things to Do in Kennebunkport, Maine, in the Fall
When autumn arrives, Kennebunkport transforms into a gold-and-crimson paradise, with crisp air and cosy charm.
18. Witness Vibrant Fall Foliage
When autumn arrives in Kennebunkport, the landscape transforms into a breathtaking canvas of gold, crimson, and burnt orange. It is New England foliage at its finest, a vivid spectacle that feels almost unreal.
Scenic Drives That Steal Your Breath
Wind your way along Ocean Avenue, where fiery sugar maples frame postcard views of the Atlantic. The contrast of sapphire water against blazing red oaks is magical. For a quieter route, Route 9 weaves through forests that glow like embers, with occasional glimpses of farmsteads and stone walls straight out of a Robert Frost poem. Roll down the windows, the crisp air carries the earthy scent of fallen leaves.
River Kayaking Through a Falling Rainbow
Paddling the Kennebunk River in October is like gliding through a shaken snow globe. Maple and birch leaves pirouette from branches, carpeting the water in gold. Time your trip for mid-morning when the sun sets the foliage ablaze, or dusk when the trees appear backlit. Watch for great blue herons standing sentinel along the banks, their silhouettes sharp against the colourful chaos.
Walks in the Woods
This hidden sanctuary offers trails that crunch underfoot with fallen leaves. The Canopy Loop immerses you in a tunnel of colour, where sunlight filters through yellowing beech leaves like stained glass. Bring your camera, the refuge’s overlook reveals a patchwork quilt of autumn hues stretching to the sea.
Cape Porpoise Pier, Kennebunkport Maine
19. Enjoy Fall Festivals & Harvest Activities:
Kennebunkport’s harvest season is a love letter to tradition, where community and nature’s bounty take centre stage.
Pumpkin Patch Trolley (Seashore Trolley Museum)
Board a vintage 1920s trolley, its wood lovingly polished, for a classic trip to the pumpkin patch. Children rush to pick out the ideal gourd as adults encircle steaming cups of cider. The smell of diesel and cinnamon combines strangely sweetly as the conductor calls for the return journey.
Apple Picking at Spiller Farm & Giles Family Farm
Spend a sun-dappled afternoon in orchards heavy with fruit. At Spiller Farm, the trees are so laden that you can pluck Honeycrisps straight from the branch. Don’t miss their cider doughnuts, hot, sugary, and best eaten under a tree with juice dripping down your chin. Giles Family Farm offers hayrides past pumpkin patches, their orange globes peeking through tangled vines.
Kennebunk Harvest Fest
The town green comes alive with the chatter of local artisans selling wool mittens and hand-thrown pottery. The air smells of woodsmoke and melted butter as lobsters steam in giant pots. Tap your foot to live bluegrass, then join the line for a slice of apple pie the size of your face.
St Ann Kennebunkport
B. Kennebunkport, Maine Winter Wonderland
Winter here isn’t just a season, it’s a mood. The first snowfall drapes the village silently, turning the harbour into a snow globe scene.
20. Experience Christmas Prelude (Early December)
This festival doesn’t just visit Kennebunkport, it possesses it, sprinkling every corner with holiday magic.
Santa‘s Lobster Boat Arrival
The crowd goes wild as a lobster boat makes its way into harbour, decks loaded with nets, and there, at the centre of the buoys, stands Santa in red waders. Children shriek with joy as he hands out candy canes from the pier.
Tree Lightings & Carolling in Dock Square
Thousands of white lights ignite the towering spruce, casting a glow on faces rosy from the cold. Strangers link arms for “Silent Night,” their breath visible in the frosty air. Nearby, a bonfire crackles, and the scent of mulled wine drifts from the Kennebunkport Inn.
Festive Shopping Pop-Ups
Local artisans sell treasures like driftwood ornaments and hand-knit hats with lobster claws. In Abacus Gallery, you’ll find whimsical wreaths made from repurposed lobster traps.
21. Embrace Winter Activities & “Paint the Town Red” (February)
When the holidays fade, Kennebunkport reveals its quieter winter soul, no less enchanting.
Sleigh Rides at Rockin’ Horse Stables
Wrapped in wool blankets, you’ll glide through snow-laden pines to the jingle of harness bells. The only sound is the horses’ breath and the occasional laugh as someone catches a snowflake on their tongue.
Ice Skating at Waterhouse Pavilion
Lace up under strands of Edison bulbs that cast a golden glow on the ice. Local teens show off spins, while beginners cling to the rails, their mittens damp with snow.
Snowshoeing Laudholm Farm’s Trails
The marshes become an otherworldly landscape of white hummocks and frozen reeds. With each crunching step, you might spot deer tracks or the delicate stitch-work of a snowshoe hare’s trail.
“Paint the Town Red” (February)
Kennebunkport’s answer to Valentine’s Day. Cosy inns offer champagne and chocolate-covered strawberries, while Earth at Hidden Pond serves a lovers’ tasting menu by firelight. The best seats? The Boathouse Restaurant’s window nooks, where waves crash dramatically against ice-crusted rocks.
Planning Your Kennebunkport Getaway: Essential Tips
Best Time to Visit
Kennebunkport shines year-round, but each season paints the town with a different brushstroke:
Summer (June–August):
- The high season bursts with energy, sun-soaked beaches, bustling docks, and lobster rolls enjoyed under bright blue skies. Expect lively crowds (especially in July and August) and book accommodations months in advance. Pro tip: Visit in late June for warm weather but thinner crowds.
Fall (September–October):
- A hidden gem for those who love crisp air and solitude. The summer masses dissipate, leaving quiet streets and fiery foliage. Hotels drop their rates, and restaurants swap summer specials for hearty chowders and apple cider. Don’t miss: The golden light on Goose Rocks Beach at sunset.
Winter (December–February):
- Pure enchantment. Snow blankets the coastline, and the Christmas Prelude festival (early December) turns the town into a holiday dream. January and February are for those who crave cosy fireside stays and empty beaches where the only footprints are yours. Pack: Wool layers and waterproof boots.
Spring (April–May):
- A season of renewal. Daffodils bloom along Ocean Avenue, and the first lobster boats return to sea. It’s ideal for budget travellers, room rates are low, and the air is fresh with salt and budding lilacs.
Getting Around: Wheels (or Trolleys) Recommended
- Car: Essential for exploring beyond Dock Square. Parking can be tight in summer, but lots near Lower Village or Gooch’s Beach are worth the walk. Note: Some beaches require parking permits(sold at local shops).
- Trolley: The Shoreline Explorer (summer only) connects Kennebunk, Kennebunkport, and beaches with no stress over parking.
- Bike: Rent wheels to cruise Ocean Avenue or the Eastern Trail, a scenic path to nearby towns.
The Colony Hotel, Kennebunkport
Where to Stay: From Luxury to Family-Friendly
- Luxury Inns:
- The Kennebunkport Inn: Dock Square’s jewel, with a rooftop bar and nautical-chic rooms.
- Tides Beach Club: Sleek and beachy, steps from Goose Rocks Beach. Their beach butler service delivers towels and cocktails to your umbrella.
- White Barn Inn: A Relais & Châteaux stunner with an award-winning restaurant and private cottages.
- Mid-Range Charm:
- Captain Fairfield Inn: A historic B&B with gourmet breakfasts and a porch perfect for people-watching.
- The Boathouse Waterfront Hotel: Right on the Kennebunk River, with balconies overlooking fishing boats.
- Family-Friendly:
- The Lodge at Turbat’s Creek: Cottages with kitchens and a heated pool.
- Nonantum Resort: Kids love the lawn games and harbour views.
Book early for summer and Christmas Prelude!
Local Etiquette: Blend In Like a Mainer
- Respect the “Private” Signs: Many stunning waterfront homes (like those near Walker’s Point) are private. Admire from the road.
- Beach Passes: Goose Rocks Beach and others require daily/weekly parking permits from May to September. Grab one at Bradley’s Hardware or online.
- Lobster Shack Rules: Order at the counter, grab a picnic table, and crack claws messily; no one judges here.
- Tipping: 20% at restaurants (many staff are seasonal workers).
Final Pro Tips:
- Photo Ops:
- Sunrise at St. Ann’s Church (the light hits the stained glass perfectly).
- Cape Porpoise Pier at golden hour, with Goat Island Lighthouse in the distance.
- Eat Like a Local:
- Breakfast: Mornings in Paris for almond croissants.
- Lunch: Clam Shack (cash only!) for lobster rolls.
- Dinner: Old Vines Wine Bar for small plates and a killer wine list.
- Souvenirs: Skip the tchotchkes, and take home sea glass from Colony Beach or a candle from Minka(which smells like Maine’s pine forests).
