Meals and Music in Kennebunkport

There’s nothing quite like some live music to take an evening of dinner and drinks up a notch or two. For a small town, Kennebunkport is home to several restaurants that highlight local Maine talent on a weekly basis. If you like your meal served with a side of music, read on for some great options located within a short walk or drive from the Captain Fairfield Inn. And don’t forget the Kennebunkport Festival (June 7th-13th), which will feature amazing musicians such as Spencer Albee, Amy & The Engine, Model Airplane, and Ghost of Paul Revere right here in town.

The Pub at One Dock

One Dock Square, Kennebunkport

Situated just off the main square, One Dock features some of Southern Maine’s most talented entertainers Thursday-Sunday nights, covering a wide variety of genres from Frank Sinatra covers to contemporary music and everything in between.

Federal Jack’s

The waterfront view from Federal Jack's

Brews, views, and tunes at Federal Jack’s – not a bad way to end the day

8 Western Avenue, Kennebunk

Fed’s is all about a brew with a view.  The original home of the Kennebunkport Brewing Company, this picturesque pub is located right on the waterfront and has both indoor and outdoor dining options (complete with heat lamps).  It’s a lively scene most nights, especially in the high season, but things really get cranked up on Friday and Saturday nights when the live music starts at 10:30pm.


181 Port Rd, Kennebunk

Why Pedro’s?  Because margaritas, a house specialty, always taste better with live music. Serving up a menu of Mexican staples, it’s Pedro’s drink menu that really shines.  The extensive list of creative margaritas, cocktails, and tequila will get you in the mood for live music on Friday nights starting at 9:00pm. 

Elements Book Bar

265 Main St, Biddeford

This hybrid coffee shop, book store, and bar is bringing back an element of much needed fun to Biddeford’s downtown. This hipster spot offers free trivia nights on Tuesdays at 7:00pm and local musicians throughout the weekend.  Visitors can tune into folk, jazz, blues, and classical performances on Friday nights or Sunday afternoons (for a more mellow vibe). Always dreamed of bring a DJ?  They also host an occasional Vinyl Night, when guests can get in on the action with their own LPs.

Atlantic Hall

173 Main St, Cape Porpoise

What started as a modest firehouse in the center of neighboring Cape Porpoise has become a historic venue for cultural events, musical and otherwise.  A highlight of the spring calendar? The return of the Rhythm Future Quartet, a 4-piece jazz band, known for their dexterity, high energy, and good humor. 


Images of Dock Square, Kennebunkport’s Village Center


You’ll pass by several art and antique galleries along Ocean Avenue as you head towards Dock Square.

When I am looking around online at various Kennebunkport attractions, they are often described as being in or near Dock Square.  But if I wasn’t familiar with Kennebunkport, I would have no idea what this means.  Perhaps because it is mentioned so many times, I might eventually guess it has some significance within this Maine coast destination.

Dock Square is considered to be the center of Kennebunkport.  Located on the Kennebunk River (about one mile upstream from where it empties into the Atlantic Ocean), it’s a hub both on water and on land (well, as much of a hub as you can get in a small Maine village).  It’s home to numerous restaurants, boutiques, antique and art galleries, ice cream shops and a small provisioning market.

I’ve posted some photos and descriptions of what you might see walking from Captain Fairfield Inn, our Kennebunkport Bed and Breakfast, to Dock Square, and then through Dock Square, over the Kennebunk River and into Lower Village Kennebunk. If you are walking directly, it takes about 5 minutes to walk from the Inn to the monument in the center; if you’re meandering, who knows… These photos were taken on a recent sunny Autumn Saturday afternoon, and even though we’ve taken this walk so many times before, we had a lovely time.