72 Hours in Portland, Maine: City Guide

I recently had the pleasure of exploring Portland, Maine. A sweet and unique little town with a huge personality. This is my guide for you if you have a quick weekend to visit, my 72 Hours in Portland, Maine: City Guide.

Day 1

I don’t think I’ve ever eaten more and at more locations than I did on this first day. IT. WAS. AMAZING. This is how day 1 went, starting at 8am with a donut. Michael went golfing with a friend in the morning while I walked to The Holy Donut, a short 12 minute walk from our Airbnb, and got the blueberry donut made with local blueberries. These babies are made with sweet potatoes so they’re dense, moist and filling like eating a giant hoagie. Took the next half hour or so to just walk around the town, find all those awesome shops and side streets and walk off the donut.

Next stop, Central Provisions, for their flavor packed Spicy Raw Beef Salad and spicy bloody mary. I only wish I had spaced out these first two spots more because I made myself almost sick continuously eating even though I was still full from the donut. It was so delicious I didn’t want to leave a single bite behind! This is one of those dishes you think about forever after and don’t even try to make at home because it will never be as delicious as they made it.

Third stop, Liquid Riot Bottling Company for a flight and meeting up with the rest of our crew than a quick stop into Eventide Oyster Co to claim a waitlist spot and off to Hunt & Alpine for the best popcorn I’ve ever had. For all you Instagrammers out there, this is the place you’ll want to take pictures, the inside is stunning. Once our spot was called, we headed back to Eventide Oyster Co for oysters with Pickled Red Onion Ice and Horseradish Ice as our oyster accouterments. When you ask anyone what you have to try when you come to Maine I’d say 99% will say a lobster roll. But not just any lobster roll. Eventide’s famous melt in your mouth Brown Butter Lobster Roll. I’m actually salivating thinking about it again. DO NOT leave Portland without eating this.

Now at this point you’ll be full, probably pretty tipsy and ready for bed…OR you could continue the night and head over to The Porthole Pub for live music on Friday nights and some dancing on the deck looking out onto the water. Phew! What a first day.

Day 2

We began our morning at Portland Pottery Cafe, a super cute little eatery connected to a pottery studio. The kind greetings from “neighbors” on our walk and the friendly service at every place we went was one of my favorite parts of Maine. You don’t get that kind of friendliness in DC. At least not usually that genuine. They had a self-serve coffee bar stocked full of their handcrafted mugs and the breakfast bagel sandwiches were the largest I’ve ever seen. I could barely finish half but I’m not a quitter.

So our day two will be different from yours as we had a wedding on Chebeague Island at the Island Inn that afternoon. Even though we went for a wedding, the ferry ride and views from the island are well worth the trip and a great experience for your second day.

Day 3

Your last day will be a travel day but don’t let that distract you from squeezing in a few more spots! We walked to The Front Room for breakfast, a clearly very popular eatery in the area because it was roughly a 30 minute wait and the line wrapped around the block. We got there just in time. Be sure to try the green tomato eggs benedict, it was oozy egg heaven, and the blood orange mimosa. During our wait, we walked down to the East End Park, gazed out at the beautiful blue water speckled with sailboats and watched people flood in with kayaks and paddle boards. We definitely would have partaken had we had more time.

Post breakfast we packed up our bags and trekked to Rising Tide Brewery spending our last hour and a half sipping local beer before our uber to the airport just 10 minutes away

Portland is one of those places I’ve always wanted to go and really wasn’t sure if I would ever have the chance. I’m so grateful that I not only got to taste the delicious food and enjoy the beautiful scenery but witness a wonderful friend get married and be surrounded by great people. Portland is a little town with a huge personality. An east coast must visit.

EXTRA TIP: Where to stay – We loved our Airbnb in Portland. Check in was self-service (which I love); it felt homey for the weekend and the location was perfect, a max 15 minute walk to everywhere we wanted to go.

Find my outfits from this post here!

Ever been to Portland yourself and have further suggestions? I’d love to hear about your favorite spots!

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