City Guide: 48 Hours in Portland, ME

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresCity Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresT. and I recently escaped Boston for a weekend getaway in Portland, ME and it was the best decision ever. Not only were we celebrating 2016, we were also celebrating our anniversary!

How to Spend 48 Hours in Portland, ME

We packed up the car and headed to Portland bright and early on the first day of the new year. It was a quick 2 hour drive, but we felt as though we were completely transported to a new part of the country.

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresCity Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares

While it feels quintessentially New England, it also has such a different vibe from Boston. One where, how do I say this nicely….people smile at each other, or hold the door when you’re rushing to get out of the cold.

Don’t worry, I’m not hating on Boston – I love it here! But, it was nice to leave the city for a few days and discover a new place.

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresInstead of totally cramming our weekend, we decided to play it by ear. We asked a few friends for recommendations and decided to go there without any solid plans.

So, what did we do? We bundled up and explored the city by foot. We walked around without a specific destination in mind and it was wonderful.

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares

We did however, eat and drink our weight’s worth of delicious food and cocktails #worthit. Here are our favorites in case you’re planning to visit!

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares

Where to eat:

  • Duckfat: If you go to Portland and don’t eat at Duckfat, did you even go to Portland?
  • Eventide: Let me start this by saying I don’t like seafood. I try so hard to enjoy it, but if you’re not fried or coconut – I’m not into it. HOWEVER, Eventide’s brown butter lobster roll was life changing.
  • Taco Escobarr: This might not be a typical Portland must-visit, but we were into it. So into it. We stopped by on our first night there for an easy meal. What we found was great service, delicious tacos, and $5 margs. Try to beat that. Just try.
  • OTTO: See Duckfat’s description above.
  • Nosh: We didn’t have the chance to eat at NOSH, but it was recommended by a few friends. Looks like they have some delicious burgers!
  • Boda: If you’re looking for Thai, here it is.
  • Central Provisions: We planned to dine at Central Provisions for our “fancy” anniversary dinner. Unfortunately they were closed for renovations (do we have the worst timing or what?). But, hoping to go next time we’re in the area!

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresCity Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresCity Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares

Where to shop:

  • Folly 101: Go here if you adore anything kitchen/food related. It took a reservation at Eventide to get me out the door. But, not before buying a new apron, of course.
  • Portland Trading Co.: Loved this little shop! It didn’t hurt that they were playing the soundtrack to Chef. Which I now want on vinyl. Feel free to get it and send it via snail mail 😉
  • Portland Dry Goods: Expensive, but good for daydreaming about new accessories and coats.
  • Pinecone + Chickadee: Too cute of a store to pass up! Some new items, some vintage – they’ve got a good mix.
  • Old Port: Basically where everything is. Go by foot, for sure!

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresCity Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresCity Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresWhere to hang:

  • Also, Old Port: Cute shops, good eats, libations, etc.
  • The Holy Donut: Sure, this could be in the “where to eat” section, but in reality if I could just hang out there all day, I would. I so so would.
  • Bard Coffee: We stopped by on our way out of the city and escaped the cold for a bit here. A cute spot!

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresWhere to stay:

  • Westin Harborview Hotel: We stayed here and loved it! Beautiful rooms, great staff, and a bar on the top floor. If you can, splurge for a room with floor-to-ceiling windows!
  • The Press Hotel: This hotel, though. We stopped in to check out the lobby and I couldn’t believe how beautiful it is. They even have a vintage typewriter you can use to type a letter! Brilliant.

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladaresWhere to drink:

  • Bramhall: This spot was suggested to me by a friend and I am SO glad she told me about it! We grabbed a few cocktails and cozied up here – it was the perfect Saturday night. Also, can’t beat that speakeasy feel.
  • Liquid Riot: I was way more impressed with this spot than I thought I would be! Good pretzels and even better whiskey.
  • Top of the East: If you’re looking for sweeping views of Portland and some great service, you must visit Top of the East in the Westin Harborview Hotel.
  • Grace: We sadly didn’t get to go here while visiting, but if you have the chance, check it out and report back! Plus, it’s in a historic church – how nifty!
  • Vena’s Fizz House: Another recommendation from a friend that we didn’t make it to. But it sure does look pretty great, doesn’t it? Cocktails and mocktails? I’m all about it.

I’m sure there are plenty that I haven’t included here – 48 hours was barely enough! What are your favorite Portland, ME spots?

g.

City Guide: How to spend 48 hours in Portland, Maine // by gabriella @gabivalladares

Author: gabriella

Gabriella is a blogger, Director of Social Media in Boston, and City Manager for the BOS Lady Project. You’ll typically find her with an iced chai in one hand and a book in the other.

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  • Oh my goodness, if you liked Holy Donut you absolutely MUST make a trip to Troy, NY to visit Nibble, Inc. Potato donuts are clearly the way to go!!

  • Sweet potato donuts, hang on what? How does that work? Ah, Portland, I couldn’t want to visit here more to be honest, it’s been on my list for years but it’s one of those places you have to really do a road trip to. Unless I could find work out there…

    Buckets & Spades

    • Literally the questions I asked, too. I don’t even know, but they are so unbelievably delicious! I think you would love Portland. It’s quaint and busy, all at the same time. And everyone there was so kind! It’s a truly wonderful place. And I bet you could find work out there, you’re so talented!

      g.

  • What a great post!

    I grew up in Maine- the midcoast area, but moved to Portland after graduation and have lived here the past 10 years. It’s fun to read about it from an outsiders perspective. The Holy Donut is definitely on are LOVE list, as is Taco Escobarr, Duckfat, Boda, and OTTO. Though I have to say, Flatbread is my favorite pizza place in Portland. Yes, there are lots of fun shops around the oldport.

    There are so many more places (ahem, restaurants) I want to recommend to you if you ever find yourself back up here for a day or weekend 🙂

    Your blog rocks. Happy anniversary, by the way 🙂

    • Thanks so much, Amber! I’d love to hear some of your other favorite spots. I’m sure we’ll plan another weekend trip up that way. And sorry for taking so long to get back to you! Travel and work got the best of me 😉

      g.

  • Hi! I stumbled across this post on Pinterest and I can’t thank you enough! I recently went to Portland and you were my guide. I went to a lot of the restaurants and places you recommended. With so many choices in Portland, I would have been so overwhelmed trying to choose where to go. Thank you so much!

  • I’ve scoured Pinterest for ideas for our upcoming Portalnd, ME trip and your blog article is the best. by far! You’ve given us a great list to choose from!