Portland, Maine

How this New England town certified itself in my books as a Grade A Hidden Gem

When was the last time you traveled somewhere new? Like brand new, where you were walking, flying, or driving in blind? It seems like this should happen often, but when I think about this question for me, even though I travel quite a bit, I realized it’s a rarity. Heck, anyone who knows me is well aware that I’ve been to Vegas 17 times and for as long as I can remember I’ve traveled to Palm Desert, CA for at least a couple weeks in the winter.

When I considered this question, the most recent place that came to mind was Portugal, which I traveled to with my brother-in-law Steve, in November 2019. However, I often overlook places that I discovered without requiring an airplane. Last September, we rented a car and drove to the Poconos, and last October we drove to New Hampshire with friends - both new spots for me.

This time, in mid-October, Lynn and I both found ourselves voluntarily unemployed (more on that in the next blog post), so we decided to find somewhere new to explore for a few days of relaxation. New Yorkers often travel north through New England during Autumn to witness the foliage, the crisp ocean air, or sample the various lobster rolls, so we figured we’d jump on that boat. With two days notice, we rented a car and a hotel room in Portland, ME, and jumped in the ~6 hour road trip to check out a new town.

We didn’t know much about Portland, other than it had about 70,000 residents, was on the ocean, and the abundance of micro-breweries on Google Maps was ridiculous. Saturday began by grabbing our Four Runner rental SUV, just a couple blocks from our Manhattan apartment. We navigated New York City, and then Eastern Seaboard traffic, passing through New York, Connecticut, Massachusetts, New Hampshire, and finally into Maine.

When we arrived in downtown Portland, we had a beautiful hotel right in the heart of the action. I went for a quick run and Lynn crushed the hotel Peleton before she took me to an insane 9-course chef’s table dinner as a celebration for my new job (again, more on that in the next post). The chef’s table was such a cool experience as we could see all of the action of the kitchen while enjoying a 9-course plant-based meal with wine pairings.

I won’t go into every detail of the next three days because it’s very repetitive: wake up, do some sort of physical activity, then focus on restaurants and breweries for the rest of the day.

Sunday was a perfect example. Run in the morning, then we walked to a cool indy coffee shop and strolled a few blocks to a tiny diner featuring an incredible vegan breakfast burrito. After that, we checked out Lone Pine brewery, then Apres cider/seltzer brewery, then Austin Street brewery. Dinner was casual at the Thirsty Pig, a local pub, and the nightcap was at Kingshead pub, a non-tourist stop for Sunday Night Football.

The beauty of having our car was the ability to get out of downtown Portland. We drove to the nearby capes on Monday to check out the ocean views at Cape Elizabeth, and Lynn sampled a pretty heroic lobster roll. Did you know that a Maine lobster roll traditionally has mayo and chives, whereas a Connecticut lobster roll has no mayo and is topped with hot melted butter? You do now.

On Tuesday we drove up north for a hike on Pleasant Mountain which was poorly named. We picked up some fresh apple cider from a family farm on the way, but once we got to the hike, we realized the fun and games were over. It was 1,900 feet of elevation in the first 1 mile (aka about 1 foot of elevation for every 3 feet of trail). After the first mile, there was another 1.4 miles of up and down before reaching the summit. Yes it was beautiful, and yes I’m glad we did it to work off all the beer sampling.

Tuesday evening we did one more little brewery tour, grabbed Thai food for dinner, and then called it an early night to gear up for the long drive home the next day.

A few cool observations about Portland, ME and why I recommend anyone to check it out if you get the chance. I actually remarked a few times during the trip that “this would be awesome for a bachelor party for someone in their 30s or 40s)!:

  • Everything is walkable. Yes the hikes are a bit further out, but all bars and restaurants are in or around downtown, and they have amazing trails that make it a very walkable city to explore.

  • The people are great. The town is made up of friendly locals, most of whom work in the tourism/hospitality industry, so everyone we interacted with was nothing but helpful and courteous, and they were proud of their town. We had countless great conversations over local beers, good food, and adventurous trails.

  • There’s community. The plethora of breweries is only possible because they’re all collaborating and are clumped together. We found 3 different stretches of buildings that were broken up into 2 - 4 sections, each section being occupied by a different brewery. Yes there’s competition, but it’s almost a “we’re in this battle together” mentality that we loved. Further, because the town is trying to stay hip, local and fresh, they literally run chains out of town. Some people we met were telling tales about how Subway and Burger King setup shop and didn’t get any support so had to close. Not many towns can claim that.

  • Vegan options. I know most readers won’t care about this, but before heading to Maine I assumed it was only hunters and lumberjacks ready to eat deer or buffalo meat 24/7. Turns out they had vegan options left, right and center, and in the right form: offering these dishes alongside non-vegan dishes at most restaurants (along with quite a few all-vegan joints, it has to be said.)

Anyway, I hope for your next short vacation, you decide to check out somewhere new, even if it’s right around the corner.