Wine and Dine Under the Stars in Kennebunkport, ME

the courtyard at the Captain Fairfield Inn

Plan your evening’s agenda from this cozy perch at the Captain Fairfield Inn

Summer in Maine, while fleeting, is in full throttle in Kennebunkport.  Spend your stay at the Captain Fairfield Inn sun-side noshing at a sidewalk table, deck, or patio. Our bustling (and sometimes bursting) village is full of opportunities to drink and dine al fresco, explore some of our favorite picks after relaxing in our courtyard with a glass of wine.

Make a smooth transition from day into night in the courtyard at Old Vines Wine Bar. Take the edge off with your vintage of choice and selections from the extensive charcuterie bar and cheese offerings, and settle in for a relaxing evening under the stars by the roaring fire pit. 173 Port Road, Kennebunk

For a more colorful experience, mosey a few doors down to Pedro’s for a New Englander’s take on classic Mexican food. The burritos and tequila are bountiful and the atmosphere is always festive. Family-style seating on the adjacent deck makes for lively and free flowing conversation. 181 Port Road, Kennebunk

The Irish spirit is alive and well in Kennebunkport. The proprietors of Ryan’s Corner House were pub owners in Ireland before opening the doors on this southern Maine outpost. This intimate, no frills bar combines traditional pub grub with more sophisticated takes on Irish cuisine, all of which can be enjoyed with a pint on the patio under twinkling white lights. 17 Western Avenue, Kennebunk

Kennebunkport Happy Hour

Strolling around Dock Square after lunch?  Looking for a place with a view where you can sit and relax?  Feeling peckish in the afternoon or hankering for a cocktail? There is one solution for all these dilemmas:  the consummate Happy Hour in Kennebunkport.

Kennebunkport restaurant appetizers

Duck Slider and Calamari at David’s KPT.

Sure, you can grab a drink at the Captain Fairfield Inn and snack on our freshly baked chocolate chip cookies, but it’s nice to have abundant opportunities for going out on the town.  These are a few fabulous options within walking distance of our boutique hotel.

Dine with a View

For expansive views, there can be no better choice than Stripers Waterside Restaurant.  Between 3 & 5 on Sundays and weekdays you can sit in adirondack chairs overlooking the river delta and beach.  Servers bring drinks right to your seat while you watch the waves and let the sun soak into your skin.

Affordably Delicious

For affordable, delicious food we favor the instantly popular David’s KPT, Kennebunkport’s newest waterfront dining destination. Just a few blocks from the Captain Fairfield Inn en route to Dock Square you can find generous, shareable dishes.  Tasty steak tartar, mouthwatering fried calamari, to-die-for duck sliders, and more for $6 or less!  The indoor/outdoor happy hour runs from 3 to 5 all week long.

Noshing Nearby

For convenience, we recommend Tia’s Topside, which is just over the bridge in Lower Village Kennebunk.  Oh no, it’s after 5?  Don’t fret, because Tia’s offers happy hour every day from 3-6PM. Get an appetizer or two, or simply enjoy 50% off alcoholic beverages.  Don’t miss out on river views from the deck!

For the Oyster Lover

Incomparable oysters harvested from Maine’s clean, cold waters can be found at each of the above hot spots as well as nearby One Dock.  Still, our pick for the oyster lover is The Hatch, located underneath Federal Jack’s.  Those on a quest for fresh, local oysters can dine happy on quite a selection.  When in town on a Wednesday, stop by between 4 & 7 for $1 oysters and $3.50 beers.

You can stay on budget and continue your appetizer round-up in the evening. Simply order some small bites for dinner at one of the area’s superb restaurants.