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Two Days in Portland Maine

Two Days in Portland Maine

The second stop on me and Carl’s Northeast road trip was Portland, Maine. You can check out more of our first stop in Newport, RI here! Portland is a cool, hipster town filled with great restaurants, breweries, lighthouses and quirky shops. In this post, I’m sharing our itinerary and how you can spend two days in Portland, Maine.


We stayed at the cutest hotel in downtown Portland called The Blind Tiger. I loved the history and character of the building. And it’s cool because it used to be a mansion and even a speakeasy during the Prohibition. I love the decor and how it feels like you’re coming home at the end of the day.

They have a pantry filled with anything you might need and their complimentary breakfast is so cute! It consists of a buffet of bamboo lid jars filled with overnight oats, eggs, fruit, scones and yogurt. And the location was perfect! It was walking distance to all the restaurants and shops.

Things to Do


Check out the cool shops and boutiques around Old Port – on Commercial Street, Moulton Street, and Exchange Street.

Go to a Brewery

Portland is filled with breweries and distilleries. Most of them also have food options and games so you can spend an afternoon there. We went to Allagash Brewing Company and Maine Beer Company. If we had enough time, we would have also checked out Bissell Brothers Brewing Company.

Visit Portland’s Head Lighthouse

Maine is filled with beautiful lighthouses, but my absolute favorite is the Portland Head Light. It’s so picturesque and has a stunning view of the coast.

Places To Eat


We had breakfast at our hotel, but here were the recommended breakfast places to try!

Becky’s Diner

Hot Suppa

Portland Pottery Cafe


Portland Lobster Co – You have to try their lobster roll!

Central Provisions – We were unable to get a reservation here, but I heard this place is so good!

Bite Into Maine – This is a food truck lunch option next to Allagash Brewing Company. I had their lobster grill cheese and it was so yummy!

Eventide Oyster Co. – OMG! This is my favorite restaurant that we went to in Portland. It was amazing. Carl and I split a bunch of rolls and appetizers, but my favorite thing on the menu was their crab roll. I loved it so much that I ordered a second one.

Street & Co – The grilled octopus was so good!


Two Fat Cats Bakery – You have to try their whoopie pies! They are amazing!

The Holy Donut – Their donuts are made from potatoes. I loved their cinnamon sugar flavor!

Two Days in Portland Maine

Hope you enjoyed my post on how to spend two days in Portland Maine 🙂

Exploring more of Maine? Check out my Acadia National Park Travel Guide

Shop My Portland Maine Outfits

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