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Finding The Best of Portland, Maine In A Weekend

Portland Head Light

Rolling into town, I didn't know what to expect. The bus station was bright, clean, and non-descript. But okay, I'm here. Now what?

My first trip to Portland, Maine, did not disappoint. I didn't make any plans before I got there, but honestly, I was a little hesitant. As a Black Woman who grew up in California, the Northeast seems like a faraway world with no relationship to my real life. But I was there. In Maine, and it was time to check it out.

How I got there:

I was in Boston, and I took the Concord Coach Lines bus from the Boston South train station. A direct bus from there to the Portland train/bus station and a bus back from there to the Boston Logan Airport was considered a round trip and cost $50.

Where I stayed:

I stayed at the Westin Harborview. Mmmmm... I don't think I would stay there again. It was a perfectly fine hotel. But I was "upgraded" to a city view room in a harbor view hotel. The room was dull, the view was boring. The breakfast at the hotel was "meh." This hotel lacked any discernible personality, theme, or good reason to stay there. Now, don't get me wrong, there was nothing wrong with the hotel, but for the money it costs to stay there, you might as well stay at the Residence Inn in the Old Port.

Exploring the cobblestone streets of the Old Port

What I did:

I visited Peaks Island on my first morning in Maine. Peaks Island is a must-do. It's a short ferry ride (15 minutes) away from the Old Port in Portland, the tickets are reasonably priced for the trip (for an adult 7.70 will get you there, and the ride back is free - seniors and children are half price).

Peaks Island is a cute little enclave. I don't think it wants to be a tourist town, but you can tell the population swells in the summertime. There were several guest houses and rooms for rent, and it is the perfect place to spend a few isolated days. Now before you head there, keep in mind that there are no grocery stores, and no medical services, and pretty much no facilities on the island. I would love to stay there to get away for a week, but I couldn't imagine living there. A lot of people do, but it wasn't for me.

Also, more important to some than others: I was on the island for about 4 hours, and I only saw one black person, and that was when I looked in the mirror. Do with that info what you will.

After Peaks Island, I went on a lighthouse tour of Portland. I mean, it's Maine, you gotta see lighthouses, right? First, we visited the most photographed lighthouse in the world, Portland Head Light. It looked just like it does in the pics, and it was a beautiful summer day, so it was great to be out there.

Spring Point Lighthouse

There is a way to climb down onto the rocks below the path to get photos from there. It's an excellent spot to get another view of the lighthouse. Now, this feels like something you shouldn't do, but there was a gate that wasn't locked, and no signs saying not to go down, and about 30 people down there, so I took my chances.

After Head Light, we went to see the Spring Point Lighthouse. This one is out at the end of a pier made of boulders and is adorable. It was a great place to see the sunset and see swimmers catching their last moments in the ocean as the sun set.

The next morning I took a walk around Downtown and the Old Port to see what else the city has to offer. Now, Portland is an odd little city, the downtown is almost too cute; it doesn't seem real, it looks fake. It has a bit of a downtown Disney feel. Most stores seem new and extra cool-hipstery, but I still liked it.

The cinnamon roll at Bam Bam Bakery

Gluten-free honey lavender donuts from Holy Donuts

What I ate:

Besides the views and the overall cuteness, the thing I like most about Portland was the food.

My first night in town, I met friends at Petite Jacqueline, and that is a restaurant I would definitely double back on. I had the Duck Au Poivre, and it was TASTY.

My last morning in town, I went hunting for pastries. My first stop was Bam Bam Bakery because I heard it's a gluten-free bakery. Now, I'm supposed to be doing Whole30, so my ass does not belong in any bakeries, but... I cheated. A LOT. At Bam Bam, I got a cinnamon roll, a slice of banana bread with chocolate chips, and a brownie (all gluten-free).

Since I was leaving at 4 am the next morning, I wanted some food for now, and some for later. The cinnamon roll was everything, So was the banana bread. But the brownie was the best gluten-free baked good I've eaten in my life (and I ate it two days later - still amazing). So based on my extremely scientific study, EVERYTHING AT BAM BAM SLAPS.

Go eat it all. You won't regret it.

More walking around town, more photo-taking, and then I realized I was pretty close to Holy Donuts. Another visitor to Portland raved about Holy Donuts the day before, and my interest was piqued. They make their donuts from Maine Potato Flour. Maine Potato Flour? Who knew this was a thing? I didn't. So you know I went to check it out. I was skeptical that the donuts were 100% gluten-free, but I had to find out. I considered it research for this post.

Holy Donuts was busy when I got there, the service was quick, but a lot of people were coming in and out to get their donut fix. At the counter, I asked if their donuts were gluten-free, and they generally are not. BUT - they did have six flavors of gluten-free donuts that day: cinnamon sugar, lemon, honey lavender, chocolate, sea salt, and coconut. I decided to get the cinnamon sugar, lemon and honey lavender (seasonal flavor) - I KNOW you aren't judging me on the number of donuts I got - this was for research purposes.

MY GAWDDDDD - that gluten-free honey lavender! Possibly the best donut I've ever had in life. Possibly. It was delicious+. I tried to get a picture of it, but I couldn't stop my mouth from continuing to bite it. The cinnamon sugar was serviceable, and the lemon was good, but the honey lavender is what Homer Simpson's dreams are made of.

For dinner, I ate at DeMillios on the water. DeMillios is an old boat that floats in the port and has been turned into a restaurant. Cute. Quaint. Overrated. My lobster was... lobstery. Our service was slow - "Walking past our table multiple times while our plates were empty without checking on us" slow. Overall, I wouldn't go back, but it's kitschy, so I see why people eat there.

The New York Sirloin at 43North.

Another night we went to 43North for dinner. I had the New York Sirloin. Absolutely Delish. We ate outside overlooking the water and were unfortunately attacked by mosquitos, so we made our exit as soon as the last bites were taken. I would go back to explore their menu further.

Bon Appetit Magazine named Portland the 2018 Restaurant City of the Year, and there's no wonder why. Everything I ate in town was delicious, and I'd love another chance to go back and eat some more.

If you're visiting the Northeast United States, you should add Portland, Maine to your list. You don't need more than 2-3 days to check it out, so it's a great weekend trip. I wish I had gone in the fall, so I could see the leaves change colors, but since I didn't, I hope you do.

Book A Perfect AirBnB in Portland, Maine

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The Ferry from Peak’s Island.

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