25 Long Wharf| 207-772-2216 | dimillos.com/restaurant | $$$
Happy Hour: 4-7 p.m. Monday-Friday, $1 off all alcoholic drinks and large list of appetizers priced from $3 to $6. DiMillo’s family-owned restaurant and lounge specializes in fresh Maine lobster, local seafood, choice cuts of beef and traditional Italian fare. The restaurant is a renovated car ferry docked in Portland Harbor that’s been a popular dining destination and gathering place since 1982.
110 Exchange St. | 207-879-4747 | cornerroomkitchenandbar.com | $$$
Happy Hour: 4-6 p.m., Monday-Friday, complimentary antipasto offered with drinks, $3 house red/white wines and prosecco, $3 draft beers. House-made pastas, breads and pizzas are the specialties of the house at this lively, Old Port restaurant, one of four in the city owned by Portland chef Harding Lee Smith. The charcuterie and wine list get raves, too.
37 Wharf St. | 207-653-7678 | bonfirepub.com | $$
Happy Hour: 4-7 p.m. daily, free bacon, plus $1, $2, and $3 food and drink specials. At Portland’s only “country-style” bar, the self-serve beer wall is the first of its kind in Maine, the music is loud, the TVs are plentiful and the crowd is wild and ready to party. All the drinks are served in red Solo cups, including a line-up of “Redneck Cocktails,” which you can sip while sitting in a tire swing.
703 Congress St. | 207-871-5005 | hotsuppa.com | $$
Happy Hour: 4-6 p.m. Tuesday-Saturday, all drinks $1 off; $1 oysters; other bar snacks $4-$6. Home-style Southern flair is the distinguishing characteristic of this cozy spot. Biscuits and sausage gravy and a fried-green tomato BLT are on the menu, along with comfort foods such as two-cheese macaroni and cheese with grilled kielbasa, or grilled cheese and creamy tomato soup.
106 High St. | 207-518-9283 | littletaphouse.com | $$$
Happy Hour: 4-7 p.m. daily, $5 Bar & Barrel (small plate with a beer) specials announced daily on Facebook, $3 glasses of house wine, $3 well cocktails. A popular spot in Portland’s West End, The Little Tap House is rustic with wine barrel tables in the bar area and simple wooden tables elsewhere. The 14 taps feature local beers and the menu focuses on upscale versions of comfort food.
The approximate cost of two dinner entrees (not including appetizers, drinks, tax and gratuity).
$ – $15 and under
$$ – $16 to $25
$$$ – $26 to $45
$$$$ – $46 and up