Kennebunkport is my home….I’m proud to say – the place of Presidents and cool people – an address so unique it’s the only place in the world so named. Friends from away ask me, “what I should do in a Kennebunkport weekend?”
Here is my perfect weekend in Kennebunkport!
First, stay on the water. You didn’t come all this way to be inland. Stay at Seaside Inn, right on Kennebunk Beach. If you are coming with kids and want an affordable spot, Rhumb Line Resort has family-friendly indoor & outdoor pools, a short walk to a tidal cove for exploring, a trolley or short drive to town.
Explore Dock Square, shop the boutiques like Minka, Fat Face, Compliments, Daytrip Society, Abacus, and browse art galleries throughout the seaside village. Have a sweet treat at Satellite Donuts, gelato at Rococo’s or homemade ice cream at Aunt Marie’s. Grab a cocktail or a nightcap and nightlife at Hurricane, Old Vines, Pedros or Pilot House – where the core locals go.
Walk Parsons Way on Ocean Ave in the early morning, past St Anne’s Church, an 1887 episcopal stone chapel on the sea, then continue by the beautiful “summer cottages” (read: grand seaside mansions) to Walkers’ Point – President Bush’s summer compound.
Take a picture at the Anchor to Windward, you’ll know it when you see it! Pass Blowing Cave and Thunder Hole on your way along the oceanfront sidewalk.
Hit the beach! Colony Beach is rocky but with a fantastic view of the boats coming and going out the breakwater, a popular place to fish too. Kennebunk Beach – across the River – is a great sandy beach – locals call it Gooch’s Beach, or beyond that on Beach Ave – headed south west – is Mother’s Beach which has a playground and fun tidal pools (at low tide). Ask your hotel for a beach guest pass for the beaches on the Kennebunk side of town. More of our favorite beaches in Kennebunkport & Kennebunk.
Rent stand up paddleboards, canoes or kayaks to explore the Kennebunk River with Kayak Excursions, just keep the tide chart handy and go with the flow turning around at high or slack tide to return with the flood as well. Wear your PFD and stay out of the main channel – paddling to the right side of the river so as not to interfere with lobster men, tour boats and pleasure craft – a local pet peeve is tourists drifting in the main channel.
Rent a Bike and tour around the oceanside roads, and the nature paths along the rivers and the Kennebunks many nature preserves..
Get aboard a lobster boat with Rugosa Tours – from the Nonantum Hotel– Captain Bob offers great narration, and the best views of Walkers Point and Goat Island Light from the water, plus you get to see how lobsters are trapped & caught & hauled.
Set sail on board The Pineapple Ketch for a sailing trip out the River, day or evening with the magnificent sunset.
Go for a fast speed pass with New England Eco Adventures on a wild open-air sea ride to lighthouses, to Ogunquit and Wells Harbor and Cape Porpoise. You may even spot seals or whales on your exciting scenic ride in this bright yellow rib boat leaving from the docks at Lower Village Kennebunk.
Warning: traditional whale watches involve a long day at sea, and the only guarantee of whale-sighting is you get to go again free if you don’t see a whale …just sayin’!
Savor Happy Hour in Dock Square, the Boathouse and Hurricane have diverse menus and great outdoor seating on the river! Arundel Wharf and Stripers overlook the Kennebunk River offering amazing sunset views and boats passing by from their waterfront Adirondack chairs. See all our favorite places for cocktails in Kennebunkport.
Wine lovers visit Old Vines Wine Bar – this cozy bistro has delightful small plates, hand-crafted cocktails, local beer, and an 
amazing wine by the glass list. Old Vines bartenders are hip and humorous. The outdoor tented patio is the place to see and be seen over a cocktail or vino!
Cheers to a great day at Kennebunkport’s Alisson’s, a classic for Maine pub fare served without fanfare in the heart of Dock Square – you get New England sports on the TV screens and a welcome vibe. Alisson’s serves Maine Lobster in many delish dishes!
The Nonantum has splendid riverfront dining and entertainment most nights, in cozy Heckman’s Pub, and rooftop Latitudes poolside drinks and fabulous local food. You will love this grand 1884 hotel on the Kennebunk Riverbank.
Visit White Columns – an 1853 Greek Revival – now home to the Kennebunkport Historical Society and the First Family Legacy Museum commemorating the Bush family’s time in Kennebunkport.
Drive out to Cape Porpoise, a classic Maine fishing village – where you can see Goat Island Light . The Cape Porpoise Pier is a true working dock, watch the lobstermen load up their bait, or haul their lobster at day’s end. Back in Cape Porpoise village, visit Farm to Table for local gifts and Bradbury’s Market to see an old fashion general store complete with Post Office.
Drive Route 35 to Summer Street, as you depart Kennebunkport, along the historic district passing the Wedding Cake House, an 1825 Federal with Gothic accents. You will also see grand seaside captains’ homes from Federal to Victorian, Italianate and Mansard – many have widow’s walks and are considered “spirited” (read: haunted). Maine is legendary for haunted houses and lighthouses. The Brick Store Museum in Kennebunk Village offers architectural walking tours for real history buffs, and ghost graveyard tours around Halloween!
So you can’t do it all in weekend. We didn’t even get to Goose Rocks Beach, the art galleries and The Art Trail of the Kennebunks, or the beautiful bike paths and farmers markets. Come to Kennebunkport Maine for a week, a month or my preference- a lifetime!
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