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Afternoon & Evening Cocktails in Old Port Portland

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Hey folks,

While my wife and I live in Saint John, New Brunswick (6 hour drive to Portland), the old port has become a second home as we make the drive about every 2 months due to the great food and overall cool vibe of the downtown area (cool shops, live music, etc). One of the things I enjoy greatly is having a few cocktails during the mid-afternoon in a place that is not too packed, with good music, service and overall atmosphere. Also, while I love the great selection of craft brews that Portland has to offer, sometimes only a cocktail will do.

Sonny's had been our go to spot for a number of reasons; great selection of homemade infused liquours, cool music, a great bar. The problem is that the service GREATLY varies depending who is working. Essentially, if the lady with blond hair is working, I just turn right around. It is really too bad because if Spencer or one of the other bartenders are there working, it is an awesome experience but she ruins everything by spending more time speaking to her co-workers then caring if I had an empty glass for 15 minutes at a near empty bar. I am a HUGE fan of Sonny's sister restaurant Local 188 who also have a great bar as well though it is generally a bit further from our hotel (Hampton Inn on Fore Street).

Thanks in advance for any recommendations".

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  1. Close to your hotel open between lunch and dinner for your afternoon cocktails - definitely no live music and I honestly have not noticed what's being played through their speakers:

    Eventide and East Ender on Middle Street.
    Eventide has great oysters and a fried oyster bun that's terrific among other great food items. Some interesting cocktails.
    East Ender more gastro pub-ish food wise. I've only had beer and wine there but they do have an interesting looking cocktail list with house infused spirits.
    A bit more slick and trendy would be Walters just off Fore St (I can't remember the cross street - across from the Portland Harbor Hotel). I've liked their apps (not as thrilled with entrees) and have had some nice cocktails. They also own Ginko Blue next door for really good music and very good cocktails though I still think the decor is out of place for Portland.
    I'm sure there are others but just not sure of that between lunch and dinner time frame.

    1. Thanks for the recs! We have been to Even Tide and like it though never thought of it as a place for cocktails. Will need to check it out.

      As far as the others, I have never been. The East Ender sounds great as we have walked by a few times and looks nice on the inside (and near Duck Fat which is a plus).

      Also just for the record, not looking for any place with live music per se, just some place where the person controlling the Satelite Radio\CD Player\iPod has some decent taste in music and is not stuck on playing 70s rock on repeat endlessly.

      1. Eventide's cocktail menu looks pretty good. Somehow I've never been to the Armory at the Regency hotel but that is a popular place and I'm sure is open all day long. Maybe a seat at the bar at the Grill Room or Corner Room. The bar at the Portland Sea Grill is really nice too and that's only a block from your hotel.

        1 Reply
        1. re: grittys457

          Thanks for the ideas. I will be sure to check out at least a few of the, when I am back in February. Thanks again folks.

        2. Hello! I hope you enjoyed your stay in Portland. We live in Portland and LOVE all the high-end restaurants in town. My favorites are Bar Lola (which I also recommend for creative cocktails -- great Manhattans!), Fore Street, Five Fifty-Five, Local 188, Bresca and Petite Jacqueline. In July, we will stay for the first time in LUBEC, Maine, and probably traveling for a day trip to ST. JOHN. I would love your dining recommendations for those areas, given your great taste (pardon the pun, haha) in our city's restaurants. I'm sure we'll hit some casual (deep fried) seafood places along the water, but on vacation I do enjoy a more upscale, reservations only, white tablecloth experience with an excellent chef and wait service. And cocktails a must for me, too! Cheers!