Portland Maine’s Best Happy Hours

Portland Maine has an amazing culinary scene, recently named a top foodie spot, and home to the best restaurants by Bon Appetit among others. But aside from sophisticated entrees and accomplished Chefs, there is also a fantastic happy hour scene in Portland. From the Old Port to the waterfront, and Portland’s best hotels, there is a lot to be happy about – especially midweek in Maine’s biggest city with drink deals and even $1.50 oysters and  free apps!

Here are some of Portland Maine’s best Happy Hours:

David’s in Monument Square has Happy Hour 3-6pm Monday-Friday $5 wines, and sangria, beers, and appetizer specials. We love David’s food and the city center setting is ideal for meeting friends.

DiMillo’s – this floating restaurant is a landmark on Portland’s waterfront, a bit touristy, but has Happy Hour with a view  Monday through Friday 4-7pm – appetizer and drinks specials. Parking is free – validated when you dine here.

Porthole – also right on the water – is casual but fun for Happy Hour deals Monday- Friday 3-6, and  Saturday –Sunday 1-4.

Old Port Sea Grill is  divey, but has daily Happy Hour 3 – 6pm with $5 Cosmos and Manhattans, $6 wines, $3 drafts, and $2.50 oysters. All day happy hour on Sunday means $5 Mimosas and Bloody Marys.

Portland Lobster Company by the water has Happy Hour Monday – Thursday 4- 7pm

Boone’s Fish House & Oyster Room on the waterfront has 4-6pm daily happy hour with
Oyster specials, $5 cocktails, $3  house wine, $2  beers and $5 food items like wings, nachos, Brussels sprouts and calamari.

The Corner Room has 4-6pm Happy Hour Monday-Friday with complimentary antipasto offered with drinks, $3 house  wines and prosecco, $3 draft beers.

The Grill Room has 4-6pm Happy Hour daily with draft beers, wines by the glass and bar snacks for $3.

Monhegan Island MaineBrian Boru – the Irish Pub has 4-7 Happy Hour Monday – Friday with $4 well drinks, house wine and Geary’s Pale Ale drafts.

Little Tap House has Happy Hour 4-7 Monday – Friday – called Bar & Barrel – a petite appetizer paired with a local beer $5, plus $5 wines.

Bonfire Country Bar has “Bacon Happier Hour” with Free bacon, $1 tacos and whiskey, $2 beer & freis, $3 wien and burgers, 407 7 days a week!

Bull Feeney gets happy Sunday-Friday from 4-7pm with $4 draft beers and 20% off singe all malts, free snacks, plus other weekly treats.

Sur Lie has Happy Hour 4-6pm with $2 off drafts, $7 wines, and culinary $5 apps.

Northpoint has Happy Hour Monday-Friday 4-6pm with $5 Drafts, $6 Wines and a $7 Cocktail, and light bites for just $6 each! Sunday happy hour is 6-10.

C2 – Congress Square’d by the Westin, offers happy hour daily 4 – 7pm. Beer specials are $4, a daily wine is $5, and a select cocktail is $7, plus half off their app menu.

Top of The East at the Westin has Happy Hour Sunday – Thursday 2-5pm with drinks specials, $6 wines, $4 beer, and an amazing rooftop view.

Grace, in an 1856 church, has Happy Hour Wednesday 5-6:30pm with $5 wine and cocktail specials, and small plate deals.

Cape Porpoise bouys used for nautical decorDock Fore isn’t fancy but it gets happy every day from 3 -7pm, draft beers $2, wine are $1 off, free appetizer display.

MJ’s Wine Bar has a great outdoor patio, and Monday – Friday 4 – 6pm Happy Hour with $5 select wines and $4.50 20oz. drafts

Vignola Cinque Terre Happy Hour is just an hour, Monday to Friday 5- 6pm with $4 select wines, half-off beer, and $3.50-$9.50 appetizers.

Maine Lighthouse

Portland Hunt + Alpine Club has happy hour with select craft cocktails for $6 Monday to Friday 4 -6pm with popcorn

Inkwell Bar and Lounge at Union, Press Hotel has “off the record “ happy hour with $5 house wine favorites, $5 well drinks, and $5 16oz local drafts Sunday- Thursday 4- 6pm.

Rosie’s has happy specials all the time – $1.50 Miller, $4 mixed well drinks, and Saturdays & Sundays $ 5Mimosas & Bloody Mary’s.

Taco Escobar offers happy hour 4-7pm Monday-Friday featuring $5 house margaritas, $3.50 select drafts, with free chips and salsa. Olé

Tomasos Canteen has 7 hours of happiness, 11-6 daily, with all kinds of drink and food deals from $2.50 beers to $6 sausage, plus nightly specials.

Bayside Bowl, on the Back Bay, has happy hour 4-6pm Monday-Thursday in summer on the rooftop deck, with half-price frozen cocktails, $2 Moosehead tall boy, and more.

Petite Jacqueline hosts
”apero” happy hour 5-6:30pm Monday-Friday at the bar and patio, with
$5 aperitifs, $4 draft beers, and $3 wine, plus $1.50 oysters, $5 small plates and $46 crepes. Mais oui!

El Rayo Taquiero gets happy 4-6 pm Monday-Friday with $5 house margaritas and sangria, $2 Sol Pacfico or Tecate.

Note: these happy hour offers are subject to change, this is just a compellation of current specials. If prices have changed or deals have been discounted – please let us know at sales@visitmaine.net, and please – don’t worry, be happy (every hour). See more Maine dining recommendations:

Portland’s Best Restaurants
Best Waterfront Dining
Top 10 Maine Restaurants

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