Road Trip Maine—Portland Bound

We woke up the next morning in a (surprisingly nice) Motel 6 in Framingham, MA, which I had never heard of before. We turned in around 10:30pm when night driving became too exhausting. We were bound for Portland, but made a stop in Salem, MA to check out some witch trial history. We were the only people on our Facebook newsfeeds who were not posting photos of white-out snowfall and shoveling out cars. In reality, I love the snow. I have ALWAYS loved snow, and it’s rare for me to purposely avoid an epic storm like this one, but allowing ourselves to follow our spontaneous get-outta-dodge instincts was more than worth it. Plus, we didn’t escape the cold—that biting, skin-piercing air attacked my face the moment we left our car in Salem. It’s a karma tradeoff, I guess.

After perusing the visitor center and the eerie and cryptic sites of the Salem witch trial hangings, we got an awesome breakfast at Ugly Mug Diner (which did in fact have very ugly mugs) and hit the road again. Rolling into Maine in the middle of January was a special experience. The water was grey and extremely choppy, but beautiful in a different kind of way. We booked a Hotwire room right in downtown Old Port for a ridiculously off-season price, but when we realized the Allagash Brewery was in Portland, we made a pit-stop before checking in. The tour and tasting were awesome (and free!), and in a slightly tipsy fashion we bought a few too many beers-to-go and souvenirs—including a $30 real leather beer koozie which was completely unnecessary (we don’t even use koozies). C’est la vie.

Portland turned out to be super awesome. It has a cute, walkable downtown and a cool nightlife scene. We had amazing seafood at Street & Co. for dinner and then bounced around in search of live music. That wasn’t hard, because our method was essentially to walk until we could hear music from the street and then wander inside. At one point, we walked by a quiet looking bar on a lonely side street that didn’t look appealing. But after hearing what we thought was live music through the wall, we gave it another shot and reluctantly walked inside. Without meaning to (and without paying), we walked into the final song at an Anna Nalick concert as she was singing “Breathe/2am”, the anthem to my angsty 18-year-old self. Could not have been more random or awesome.

In true NYC girl fashion, I was lulled to sleep in my hotel that night to the sounds of chatty partiers on the streets outside.

The next day, we set out to explore the area and take a long walk along the water. The snow was glistening and the water was bright blue, which made the chilly air more than bearable. We took the Fort Sumner Park Steps to get a more aerial view of the landscape, despite the fact that they were almost entirely covered in ice and I was one misstep away from tumbling down the hill and into a snowdrift. The fresh breeze nursed my one-too-many-beers-last-night body back to health and prepped us for our last (quieter) night in Maine.

We hadn’t booked a second night at the hotel just in case we felt compelled to jet off into the horizon. But we were having fun in Portland and this was one of the fanciest hotels we’d stayed at in a while, with free breakfast and a 3-piece sectional couch in the room (thanks to off-off-season pricing). Since we’re not big on paying full price, instead of going to the front desk and extending our stay, we re-booked a second night on my Hotwire app when we were 3 blocks away from the hotel. We got a slightly puzzled look when we told them we needed to check out and immediately check back into the same room, but it was worth the $$ saved. Travel tip—always circumvent the system when possible.

We had a nice dinner of mini-plates at Central Provisions which included a disturbingly good plate of caramelized sheep’s cheese melted into sweet grilled pears to form a crispy patty of flavor. We wandered off for an after-dinner drink at Bar of Chocolate which boasts chocolate desserts and martinis. Espresso martinis are the dessert of champions.

Our hotel window looked out over the snowy rooftops of Portland, into quiet streets and crispy air. I liked our calming little city, and it was nice to be somewhere with awesome food, a cool scene, and a manageable size. I talk about my affinity for smaller cities all the time, but I don’t mean to bash my “hometown”. I love New York, but sometimes it’s easier to appreciate a place that’s a bit more intimate.

Goodnight, Portland. Tomorrow, we would be backtracking to Portsmouth, NH, an old haunt of ours.