Portland, Maine: Encounters with Kindness

When my friends and I decided to take a girls’ trip to Portland, no one told us that Maineites??? Mainers would give Southerners a run for our money where hospitality is concerned.

Case in point: While taking a break on the Back Cove Trail that was filled with walkers, joggers, and bikers, a female jogger literally stopped mid-stride to approach us.

“Are you all OK? Do you need directions anywhere? I see that you’re tourists because you all have matching bikes,” she said while motioning to our orange rentals, “so I wanted to help.”

We were floored. This woman stopped her exercise routine for us?! After receiving directions from her and admiring once again the people, we continued on our way. This was not our first, nor would it be our last, encounter with kindness. People waved from the street as we drove by, were courteous drivers, asked if we were models (that’s always a way to a girl’s heart), and the list goes on.

Unlike Get Out where the interactions were sinister, all five of us Black women felt like the people were genuine and just happy to have visitors. Admittedly, we were all reticent about how the residents would receive a group of Black women in a state known for its maple syrup and lobster rolls but not for its diversity.

Of course, now that I’m 20+ hours away from the States I would love to return to Maine again with my mom. When I was living in NYC, I never took the hour or so ride plane ride up to the state even though my co-workers spoke highly of it.

If you decide to visit too, here are some suggestions:

1.) Eateries

Oyster bars (though I despise raw oysters and will only eat them fried), dried herbs hanging from the rafters, floor to ceiling glass windows, and goodness. I was expecting many things from Maine, but stellar eating was not one of them. The food was decadent: lobster rolls on fresh bread, clam chowder, skate fish, and seasoning. People know how to season up their food right!

Suggested places: Scales (large beautiful windows with views of the waterfront), Street & Co, and Eventide Oyster Co. 

2.) The Holy Donut

I know I just wrote about eateries, but this place deserves a section to itself. Famous for its cake donuts, I would suggest buying a variety, quartering the donuts, and indulging with friends. From pomegranate to sweet potato with ginger sugar, my friends and I went to Holy Donut every day. The real secret is the gorgeously flavorful homemade frittatas: English muffin, sausage, fresh cheese, and pesto. Need I say more?

Our greedy asses culinarily curious selves agreed we would be splitting some frittatas within the group. We left the store only to go through the drive-thru and order more frittatas. An early arrival is needed because they sell a very limited amount each day.

3.) Acadia National Park

Full disclosure, I’m not a fan of hiking. I’m only a recent fan of walking, come to think of it. I was such a late walker as an infant my mom took me to the doctor to see if something was wrong. The doctor’s response? Put her down. You carry her too much. I was doing the Ariana Grande and Mariah Carey “carry my everywhere” routine from the jump. As a result, my childhood nickname was chicken legs for good reason.

I tell you all this to say I’ll never be the person to say let’s go on a hike.

Hiking for four hours is exactly what I did in Acadia National Park though. My favorite part was sitting, reclining, pausing on the rock as the Atlantic’s waves crashed below me. That mixed with sunshine and a breeze was all I needed.

Note: Renting a car and driving three hours is needed to visit Acadia National Park.

4.) The Portland Freedom Trail & Biking 

As I mentioned earlier, my girls and I biked around Portland. Stop at Cycle Mania to get outfitted with helmets and bikes. The shop is close to the Back Cove trail where the kind runner offered to help us.

After biking that trail, bike to the city center–which takes you on a lovely path passing boats bobbing in the water and a life-sized choo-choo train. Some hills may leave you huffing and puffing, but it’s all good. I wanted to explore Maine’s underground railroad, so my girls and I locked the bikes and set off on foot.

Of course, I got us lost when trying to find the first destination, but we eventually got on track. Disappointingly, all of the buildings except for one are no longer standing. They’ve either been lost to Portland’s Great Fire or new construction/gentrification. Plaques are all that remain.

When my friends and I found the Abyssinian Meeting House, a woman with black overalls and a side braid hopped off a pile of lumber and gave us an impromptu history lesson of the building (yet another example of people’s kindness). The building was about to get demolished, yet for $300.00 one of the oldest Black families in Maine purchased the place. To think that such an important monument of Black, no American, history was going to be gone for the price of roundtrip plane ticket from Houston to NYC was chilling.

A non-profit organization has been trying to restore the building to museum level quality since 2000! It’s not open to the public, but hopefully one day it will be.

Note: The locals we asked about the trail had never heard of it. Some links to the map online were broken. Here’s the PDF guide to the trail.

Enjoy Maine if you can!


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