Portland, Maine – East Coast Road Trip Part Two

Hi friends, welcome back! I’m sharing part two of my time in Portland, Maine today, so be sure to check out my last post if you haven’t already. On our first full day in Portland, I signed Jon and I up for a historic walking tour. We had never done one before, so we were excited to learn about the city while getting a lay of the land.

We stopped at Higher Grounds on the way for some delicious cold brew.

There were two other tour participants, plus the guide, so we lucked out with an intimate tour. The tours usually have 12-20 people, but due to the virus and being off season, we had a nice, small group. We wore masks and were outside all of the time, so we felt safe. Portland is a great city for a walking tour because you can see almost everything in a few hours. You can generally get anywhere by foot in 15-20 minutes, a lot smaller than NYC!

I learned that Portland burned down four different times, so unfortunately there aren’t many old buildings in the city. After the fourth time, the people got smarter and started building with bricks instead as you can see.

If you look closely, this building has a cannonball stuck in it from a British attack during the Revolutionary War. They left it in the building as a big screw you to the British ha!

Portland was also a key place on the Freedom Trail and where the abolitionist movement started, and the city has quite a few plaques by the significant places that were interesting to read.

A photo with the Maine Lobsterman, all that’s missing is his beloved dog.

We stopped by the famous poet Henry Wadsworth Longfellow’s house, unfortunately we couldn’t go inside, but the house and garden were beautiful! I have heard that the inside of the house is worth getting a tour and his sister made sure to keep everything as it was during his lifetime.

How grand is this city hall! Originally, Portland thought it would be one of the largest cities in the US, so it created the City Hall to reflect that. Nowadays about 60,000 people live in the city center.

Our tour ended with cookies from Standard Baking Co. Yum!!

Out of all the restaurants in Portland, I was most excited to try Duckfat! This is one of the most popular restaurants in the city and always has a long wait. We went at 1pm on a Thursday during the pandemic and it was packed with an hour wait. Good thing we had our cookies!

We started with “The Original” Duckfat vanilla milkshake – delicious!

For our appetizer, we ordered the Poutine with a sunny side up egg and slow cooked duck confit. This was even more delicious than it looks! I’ve never had duck like this before, but I really enjoyed it!

Jon and I decided to split a duck confit panini, and this was a great idea – we were both STUFFED after this meal! This panini also had goat cheese, sour cherry mostarda, and the most amazing brussels sprouts slaw.

Highly recommend ordering this exact meal if you go, you WILL NOT be disappointed!

After lunch we walked to the coast and around the city to prevent a food coma.

You can see how the Old Port has been kept as is and laws have been passed to preserve the port and prevent this area from turning into hotels/housing.

Thanks for reading part two of my Portland, Maine trip, stayed tuned for the final installment before moving on to Bar Harbor/Acadia National Park.

12 thoughts on “Portland, Maine – East Coast Road Trip Part Two

  1. I love how quaint Portland looks. The brick buildings, the cobblestone streets, the Old Port, little bits of history scattered around and having just read Part I, I can see the city offers some beautiful hiking paths. Seems like a perfect getaway place. Thanks for sharing!

  2. I also remember my visit to Portland, I liked the harbour area with its pedestrian streets and quaint shops. You’ve taken good pictures of them. Thanks.

  3. I’m guessing you visited on one of the last nice weekends before winter – the weather looked great. Also, “mostarda”? Cool word!

    1. Yes – it actually snowed near the end of our trip – was not prepared for the cold! Haha I had never seen that word before – I guess we are always learning!

  4. Portland definitely has a space on my travel bucketlist after this, i love how cosy the town looks, the history, I’m a sucker for history so sign me up already, let’s not forget the pictures, they were stunning 💕
    Thank you for sharing this

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