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A Weekend Jaunt to Portland Maine


Matthew Simko in Portland Maine

Earlier this month, Dave and I took a fantastic weekend trip to Portland Maine. About 2 hours north of Boston, Portland has become a New England food mecca in recent years. We decided to ditch the car for the weekend and take the Amtrak Downeaster Train to Maine, and boy are we glad that we did. For the approximately 2 hour train ride from Boston to Portland, we sat is big comfortable chairs and watched the beautiful New England scenery pass by. As a blogger and social media junkie, I’m addicted to my phone so the free wifi more than came in handy for those moments along the route where cell service was sparse. Because we like to drink in the morning, Dave was kind enough to head down to the cafe car and get us mimosas to sip on while we made the journey.

Dozen Oysters at Eventide Portland Maine

As we arrived in Portland, we quickly Ubered over to The Pomegranate Inn located in the West End of Portland. This quirky in is steeped in history and defines the work “charming”. We were greeted by Innkeeper Landon who checked us in and held our bags while we strolled into town to explore. Being oyster snobs, our first stop was the highly recommended Eventide. After a short wait, we bellied up to the bar for a beers and a dozen oysters… an appetizer of sorts to start off the day. Not having a car in town actually made it easier by alleviating the need for finding parking or feeding a meter is we did find a spot. It also allowed us to imbibe a bit more without any concern. And we sure do like to imbibe.

Saturday afternoon would prove to be my first of 3 stops during the weekend at Holy Donuts tucked smack dab in the middle of Old Port. Their donuts are made with mashed potatoes, ACTUAL mashed potatoes mixed in to the batter which gives them a uniquely dense, but light texture. With a little (strong) afternoon buzz, I downed a raised sugar chocolate donut and a savory cheddar and bacon donut. I don’t regret a single second of that decision.

West End Portland Maine

Around sunset, we strolled back to the Pomegranate Inn taking in the sites of the beautiful homes in the West End historic house district. Most were decorated for Christmas and were beyond impressive. As we entered the Pomegranate Inn, afternoon sweet snacks were laid out in the breakfast room complete with every single Keurig K-cup you can imagine. We grabbed, a snack, brewed a cup, and headed up to our gorgeous King suite.

Complete with fireplace, sitting area, and luxuriously plush king size bed, the room did not disappoint. Carrying the quirky theme throughout, our room featured hand painted walls in a gorgeous bird pattern. It was one of the most awe inspiring guest rooms I’ve seen in recent memory.

​After a restful night sleep, we meandered down to the breakfast room for an absolutely delicious breakfast, a signature of the Pomegranate Inn. Waffles, fresh fruit, and an assortment of scones were on the menu. We chose to eat and sip our coffee in the sitting room where we plotted out our day. Before we headed out, I met with fellow Boston blogger Kristen Uekermann of The Boston Fashionista. We snapped a few photos in front of

the inn which served as a perfect background for an autumn photo shoot.

Sunday was a chilly rainy day in town. After a quick stop at Duckfat, we were ready to head back to Boston on a warm comfortable train. Taking the train proved to be a relaxing way to travel home without the worry of traffic or delays which seem to have a way of ruining relaxing weekend trips. Evening selections in the cafe car included local favorites like Wicked Whoopie pies and a delicious little fruit and cheese box which we enjoyed with a bottle of (contraband) 90+ Cellars L’amis Barbaresco.

Like what you see here? Follow me on Instagram, Twitter and SnapChat for more pictures from my #DowneasterGetaway. @SimkoSays on all social media.

Amtrak is offering a Train to Maine BOGO deal to Freeport and Portland and a Take 5 Deal where with the purchase of one adult full price ticket, passangers can bring up to 5 friends for only $5 each way. Follow Amtrak Downeaster on Facebook, Twitter, Pinterest and Instagram and use the #DowneasterGetaway and #TrainToMaine on your trip.

Amtrak Downeaster provided transportation and compensation in exchange for digital content. The Pomegranate Inn provided lodging in exchange for inclusion in this blog post.

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