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Where to Eat in Portland, Maine

This weekend was very special. Friday the 13th was my birthday. I turned 45. Closer to fifty than forty. Ugh.

Never a fan of my birthday, even when I was a kid, each birthday gets more difficult for me. I have always seen it as a negative, a reminder of getting older. Like anyone is really a fan of aging, right? I look in the mirror lately and see all only my flaws. Crows feet. Laugh lines. Gray hairs and stray hairs.

I always hated birthday parties or birthday celebrations of any kind. Just another reminder. Maybe it won’t happen if no one acknowledges it, right? Wrong.  Each May 13th I still get a year older, no matter how hard I try.

That being said, this year I wanted it to be different. To have a different outlook. To be more positive about something out of my power to change. So, to kill two birds with one stone, I planned a romantic weekend away in Portland, Maine.

Even though it’s only an hour and a half away, I had never been there. WOW! Was I missing out! What a wonderful city.

We stayed at Portland Regency Hotel and Spa in Old Port. This is a gorgeous, 95 room hotel housed in what used to be considered one of the best and well-equipped armories in New England.  It is two blocks from the waterfront and centrally located to a ton of unique shops and restaurants.

Historic Old Port is one of the country’s few working harbors and boasts beautiful architecture and cobblestone streets. There is something to see around every corner, whether it be to stop and enjoy the sounds of the street musicians or take a break and enjoy a drink at one of the many eatery’s outdoor patios.

Portland is a foodie paradise. There is something for everyone from casual to fine dining. If you aren’t sure where to eat, hop on a foodie bus tour or just stand next to a sign on the sidewalk that says “Foodie tour meets here. Your guide will be with you shortly”.

Many of the restaurants serve small plates and tasters, which we enjoyed as it allowed us an opportunity to sample so many amazing things.

If you are planning a trip to Portland, I hope you find some of these recommendations helpful.

If you aren’t planning a trip to Portland, you must.


This bakery should be called “Cool Cats”. Totally unpretentious, this no-frills bakery had the greatest people who were so fun and friendly and down to earth. I kinda wanted to hang with them all day and “Like, just bake maaaan”. The sour cherry pie was simply amazing. I may or may not have bought one all for myself and ate it with my fingers in the hotel room like a savage. We stopped back before heading home to pick up a couple of pie sampler boxes to take home for family. They actually made it home!


A Portland landmark, we stopped at DiMillo’s on the Water for some appetizers. The burrata cheese with fresh fruit was so refreshing and light. The total opposite of the Braised Short Rib Poutine. I would go back for that cheese plate alone.


Then there was Street and Co. This restaurant was in a league of its own. A beautiful, old building with exposed wooden beams, soft lighting and a smooth, poured concrete bar packed with ice and fresh oysters created a relaxed, inviting atmosphere. There is an extensive wine list to choose from and the menu is unlike any you’ve likely come across.  Steel skillets were brought to the table piping hot. We ordered Mussels Provencal with garlic, white wine and butter served with freshly baked artisan bread to sop up all that delicious, fragrant broth and grilled lobster served on linguine with butter and garlic. As a taster, we enjoyed sweet cherry peppers stuffed with creamy halibut and a saffron aioli. We were lucky enough to grab a seat at the bar. It is suggested to make reservations well in advance.

On our first night, we ate at a tiny eatery called Hot Suppa which is located in Portland’s West End. It is Southern soul food right here in Maine. Friendly, inviting and simply delicious. We sampled fried oysters in a chipotle Beure Blanc with hot pepper relish, fried chicken and grits. A bit off the beaten path, but well worth it.

We also made a stop for Thai at Boda. The food was fresh and delicious and we were able to try a few things with their small plates. Their pad thai was out of this world, spicy quail eggs served with soy sauce and scallions, shrimp and pork belly skewers with orange, ginger, garlic soy sauce. I am still drooling over the pork belly.

After watching Phantom Gourmet, we decided we had to make a stop at Duckfat which was supposed to have absolutely amazing fries and milkshakes. It was meh. The fries were very salty and the milkshake was thick, creamy and delicious. Like a milkshake. The restaurant itself was so small, I had to sit with one cheek on a tiny stool and the other on the poor man next to me, that happened to not be my husband. It did not lend to a great experience.

The other Phantom Gourmet recommended restaurant was Holy Donuts made with Maine mashed potatoes. It had to be good. The line was out the door,  I picked up a half dozen of assorted donuts in somewhat odd flavors like, chocolate sea salt, mojito, maple bacon, lemon and cinnamon sugar. I’ve never met a donut I didn’t like, until now. I found the texture to be mushy but dry, if that’s possible. The flavors were very fresh, but actually a bit strong. I got an iced coffee as well, and it was so strong, I couldn’t drink it. That’s saying something because I like my coffee strong.

Skip the hype at Duckfat and Holy Donuts if you make the trip.




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