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, or Breakwater Inn and Spa and the Boathouse Waterfront Hotel both have great locations on the river. Or Captain Lord Mansion is a super romantic B&B. Inn at English Meadows in Lower Village is as well, a bit more mod and chic. If you are coming with kids and want an affordable spot, Rhumb Line Resort has indoor & outdoor pools, a short walk to the water.
Get drinks at Stripers overlooking the Kennebunk River and sea, this is a spectacular spot at sunset – part of the Breakwater Inn and Spa.
Explore Dock Square, the boutiques, shops, galleries, have a sweet treat at Satellite Donuts, gelato at Rococo’s or Aunt Marie’s, or a nightcap and nightlife at Boathouse, Hurricane, Burleigh, Pedros or Pilot House – where the core locals go.
In the early morning, walk out Parsons Way on Ocean Ave 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.
You can 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.
A fun lobster tour boat ride is aboard Rugosa – 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.
If you prefer to set sail, The Pineapple Ketch and Schooner Eleanor both make daily sailing trips out the River. Or go fish with Captain Bruce aboard Libreti Rose II.
Warning: whale watches involve a long day at sea…just sayin!
For Happy Hour in Dock Square, the Boathouse has a diverse menu and great outdoor seating on the river! See all our favorite places for cocktails in Kennebunkport.
Wine lovers should 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 Cheers of Kennebunkport is Alisson’s, 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.
95 Ocean at the Nonantum has riverfront dining and entertainment most nights in this grand 1884 hotel on the Kennebunk River bank.
Visit White Columns – an1853 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.
As you depart Kennebunkport, drive Route 35 to Summer Street 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). The Brick Store Museum in Kennebunk Village offers architectural walking tours for real history buffs.
So you can’t do it all in weekend. We didn’t even get to Goose Rocks Beach, the art galleries and 2nd Friday Art Walks in Kennebunkport, Lower Village and downtown Kennebunk, 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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