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Nov 17, 2013 08:59 AM

Thanksgiving for 2 in Portland

Any ideas on where a couple of out-of-towners from NYC should eat on Thanksgiving Day in downtown Portland? (We won't have a car.) I've gone through the list of restaurants that will be open, and the options are slim.

The Thanksgiving menu that most appeals to us (we love seafood!) is Eve's at the Garden at Portland Harbor Hotel, but they've been sold out as of the first week of November. It's a $45 buffet with oysters, shrimp cocktails, seafood chowder, the Thanksgiving staples like turkey/ham/prime rib, and more creative sides such as crab & saffron couscous and edamame salad w/ chorizo.

Now that our top choice is all sold out, we're debating whether to pack a picnic from NYC and heat it up in our hotel room, or "splurge" on options that don't seem very exciting. We'd love to pick up supplies locally, but our flight arrives at 11 a.m. on Thanksgiving Day and from what I've heard, everything's closed, including local bakeries.

We'd love your help, Portland food lovers!

1. Which is the best pick, if your options were limited to the following on Thanksgiving Day?

A. Five Fifty-Five: $75 4-course prix-fixe menu ( Would this disappoint two New Yorkers? Value for $ is important to us. We don't mind spending $100+ pp if the food will impress us. Let us know if you think it's worth it!

B. Twenty Milk Street at the Regency Hotel: a la carte with appetizers around $12 and entrees around $30 ( How's the food there? We couldn't find any positive/recent reviews.

C: Denny's. We've never eaten at one, and it could be an interesting kitschy experience.

2. Where could we go for dinner/drinks? We're thinking of Three Dollar Deweys, but would love to hear which other places will be open.

3. Any other suggestions?


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  1. Tough one. Where are you staying?
    Of your picks, I'd have to say 555. They do an excellent job although some people love it more than others. Of the group, it really should be head and shoulders above the rest.
    Twenty Milk has potential for good food although most locals tend to avoid the hotels just because, well... just because we avoid the hotels.
    Denny's is a piece of, uh, Americana. It's actually a pretty good walk from downtown through a crappy part of town but should bring back memories of Swanson TV dinners you used to have as a kid. My guess is that it's probably a pretty sad place on Thanksgiving.
    3 Dollar Dewey's fair basic pub food with about 20 beers on tap - actually pretty poor beer selection considering how many options they have but definitely an ok choice to hang out in and maybe watch a football game. They do have some good local choices in bottles.
    The North Point is also advertising a Thanksgiving Day deal for $35 pp. I like their food, drink, and the space is great (no TV). Might be a good option.
    If you're adventurous, check out the Inn on Peaks - a 20 minute ferry ride from the Old Port. I know they'll be open though not sure what they're serving that day - it would certainly be a unique way to spend the day. Call them first.

    2 Replies
    1. re: bobbert

      Thanks! The North Point sounds great. I just called and they said they'll be open from 2 p.m. to midnight and taking walk-ins.

      We're staying at the Hampton Inn downtown on Fore Street.

      Inn on Peaks sounds interesting as well. They're offering a $19 buffet with all the traditional Thanksgiving dishes and open until 3 p.m.

      Now we'll have to decide where to go for lunch vs. dinner.

      1. re: Noodle fanatic

        North Point and ferry terminal are both very close to your hotel. North Point owners happen to be ex-pats from nyc.

    2. I would definitely go with either Twenty Milk Street or 555. I understand what Bobbert is saying below. Typically, restaurants situated in hotels are, well, in hotels. But I was pretty impressed with the food at this place. And the ambience is decidedly NOT hotelish. Lighting is low, tables are spaced nicely apart, linens are high end and clean, cutlery is fine, staff is professional and knowedgeable. And, the food was really really good. I bet they do a nice Thanksgiving. 555 is also an exceptional experience, too, though. I had the MOST yummy escargot I have EVER had in my life there. I will never forget it. The ambience there is really nice as well. I like the upstairs tables.

      I'd go with either of those places and then bar hop your way back to the Hampton. You can't go wrong!

      I've gotten great advice from NY chowhounds. I hope your experience in the beautiful state of Maine is a good one. Let us know your thoughts.