Happy Hour Portland, ME | Late Night Happy Hour | Crooners & Cocktails

Crooners & Cocktails: The Skinny on Happy Hour

Happy Hour Portland Maine

Crooners & Cocktails has the kind of razzmatazz that Ol’ Blue Eyes would be proud of. Although Chicago was Sinatra’s kind of town, I like to think he’d appreciate Portland, Maine, and the abundance of Happy Hour deals (especially those featuring his favorite gasoline, Jack Daniels Tennessee Whiskey.)

Choosing a watering hole can be frustrating, thanks to an average of 230 restaurants in the area. The pressure to offer something different to patrons is high… and Crooners & Cocktails is the first of its kind here. 

Photo by Ben Moore

This “throwback supper club” is an ode to the Rat Pack Era, where cool cats and chicks can hang loose, sip martinis, and catch a black and white flick on the TV’s. Frank Sinatra and Dean Martin croon from the music machine and plush leather bar stools invite those feeling particularly thirsty to take a load off.

Crooners & Cocktails offers several specials for their Happy Hours.

(Yes, two Happy Hours! 4-6pm and 11pm-1am)

$4 Drafts

$5 Select Red & White Wines

$5 Cosmos

$5 Frank Sinatras (Three fingers of Jack Daniels, two rocks, one splash of water)

$4 Bar Snacks (including homemade meatballs, daily deviled eggs, and dates wrapped in bacon)

Photo by J.Frederickson

Photo by J.Frederickson

When I arrived at 5pm, the mahogany bar had several groups of sharp ladies sipping on bright pink cosmos. Naturally, I was jazzed to give this old school classic a try of my own. I was pleased to discover my Cosmo wasn’t too sweet and had the perfect tart taste. I did, however, wish some of their other house cocktails would appear on the Happy Hour menu. The Twist and Shout (Stoli Ohranj, St. Germain, Topped with Prosecco) and the Beet of my Own Drum (Bacardi White Rum, Fresh Beet Juice, Grand Marnier and a Spritz of Truffle Oil) will be calling me back to taste another time.

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Photo by J.Frederickson

It’s obvious that the owners considered the little details in this establishment. Crooners & Cocktails offers only 39 seats but manages to add comfort with roomy leather bar stools and dining chairs. A giant mirror on one wall offers perspective. Hooks live under the bar top for purse storage. Numerous outlets can be found under the bar for those of us who need to recharge our phones.

If you really want to be in the groove, Crooner’s & Cocktails recently started a “Martini Club.” Similar to many “Mug Clubs” at breweries, an annual membership of $100 will deliver an exclusive menu of $5 martinis in your very own martini glass.

So, if you’re feeling in a slump and want to try something different, Crooners & Cocktails has just that. Belly up to the bar, sip on some ol’ Jack Daniels, and let the music of Frank Sinatra fly you to the moon.

The Skinny (What You Need to Know)

WHERE TO FIND:  90 Exchange St., Portland, Maine

WHAT TO CALL: 207-536-0469  

WEBSITE: croonersandcocktails.com

HOURS: Cocktails & Bar Snacks: 4pm-1am Tuesday through Saturday | Full Dinner Service: 4-10pm every night | Sunday Brunch: 10am-3pm | Happy Hour: 4-6pm & 11pm-1am

PERKS: Happy Hour, Late Night Happy Hour, Martini Club, Purse Hooks & Outlets for Charging at the Bar, Snacks, Dinner Service, Dinner and a Movie

PARKING: Street Parking

WHY YOU NEED TO GO:  It’s a perfect excuse to time travel back to the Rat Pack Era and brush up on your 50’s & 60’s slang… you dig? Also, two Happy Hours is a positive plus in my book.




About Jennifer Frederickson

Jenn is a Food & Beverage enthusiast who may or may not be addicted to Wickles Pickles, Sparking Rose, and Sour Beers.