As I began Day 1 of the actual trip, I awoke to the sounds of seagulls, the smell of the bay, and accents both alien and amusing. My beautiful accommodations at the Portland Regency were most welcoming. I was treated to complimentary coffee and pastries after my visit to the fitness center, jacuzzi, sauna, and steam room. The team and I headed to Market Street Eatery for breakfast wraps. It’s a cute comfortable quick stop with lots of menu options and grab and go drinks. A perfect space to prepare before meeting with one of Maine’s most prominent train activists.

Wayne Davis is as gregarious as he is impressive. Thirty years ago, he took an ad out in the local paper and met with twenty other Mainers in a bank conference room. This slowly but surely turned into what we know as the Downeaster today. It is a story of community activism, perseverance, and determination. Wayne shared his history with me as we rode aboard Maine’s Train. 

We hopped off in Freeport and meandered towards the Harraseeket Inn, a long standing icon along Freeport’s main drag. The original owner was incredibly supportive of both the local farm to table crowd as well as TrainRiders NE and their mission to launch the Downeaster. We snacked on the daily buffet offerings and chatted about the future of activism to come. Wayne left me with some important advice for those of us coming to age in this tumultuous climate – remain diligent, keep a close eye on who we send to represent our population and always keep hope.

After a quick visit to the well known L.L. Bean center and a great photo op by the Big Boot, Wayne and crew took me to meet Patricia Quinn. Patricia is a real inspiration to women in transportation. Not unlike the culinary world, the transportation field is often filled with teams of men. This is contradictory when you consider more women and gender non-conforming people really on exclusively public transit in the US. She welcomed us to her office and told me about how she got into the industry as well as its future from her perspective. She was on the team for the inaugural ride of the Downeaster and her work is a testimony to how investment in public rail can radically change people’s lives and career goals in unexpected ways.

Having wrapped up an inspiring day, I was called to hunt down an inspiring meal. On recommendation from a colleague I ventured over to Eventide to sample their oyster bar and sparkling rosé specials. I completely understand why this location is constantly buzzing. After winding my way through a line out the door, I witnessed a mastery of chaos by the staff at large. Birthdays, Bridal Showers, and tables full of hipster foodies kept the waitstaff lapping the small space at a speed that only retire industry vets can endure. It is a beautiful space, easy to photograph and appreciated by locals and tourists one in the same. 

While their menu had a mix of old standards and playful concoctions, the variety of their oyster selection is what I was after. I was sat at the bar and given welcome by a bartender with a classic Maine accent and a wide confident smile. I asked her if she grew up in the area and if she would be confident picking a selection of oysters for me to sample. She nodded and whipped her head towards the man with the shucking glove gave him a second nod and a few moments later I had a cacophony of halfshells. I love oysters but to experience a variety of such different flavors, textures, shapes… that was a very new experience for me personally.

The next day brought me to Peaks Island. By recommendation of the hotel’s front desk staff, I hopped on the ferry to check out one of the most interesting and unexpected places just off Portland’s shore. The Umbrella Cover Museum, a quirky little Guinness World Record Holder stole my heart. The owner and director Nancy 3 took me through her exhibits, collections, and taught me her slogan – Celebrate the Mundane! Her massive collection of umbrella covers curated into categories from over 40 different countries was a fun and informative stop. Nancy has a way of working something most people consider frivolous into a lively little museum with a beautiful sense of whimsy. 

I also made a stop at Millie’s Skillet for clam cakes and fried Brussels sprouts. I had never had a clam cake before and the crispy delicious crunch is extremely satisfying. I feel a little deprived having never had this before honestly. The 2 person operation located right on the waterfront has been serving the island and its visiting tourists for over 4 years and judging by the line coming off the ferry, it is a much appreciated break from the tradition inns and taverns that also line the main drag. With menu prices between $7 – $15, it provides a great meal at a more affordable price point.

The final day in Portland was rainy and slow paced. I made my way down to the Regency’s fitness center and spa soaking up the jacuzzi, sauna, and spa included in the amenities for all guests. It was a really nice treat sipping cucumber water and getting a little free time before the next leg of the trip began. The Spa Director and I got a moment to chat about the array of products and services their team provides. Using lots of natural products and traditional techniques, the spa is a big reason many guests choose their location for any Portland stay. 

That evening, I headed over to MJ’s Wine Bar for a tasting with the owner Mark Ohlson. MJ’s is a fantastic bar obviously crafted with love. As you enter the wall of wine to the left and sweeping interactive mural to the right frame a cozy community with a tall communal table, large inviting bar, and an array of lounge chairs and sofas. Mark told me about how he works to make wine accessible to those who may not have grown up with it.

While some consider Portland a beer town, Mark teaches wine tasting classes weekly and has travelled all over the world to bring the best to his community. We sipped four French whites and the difference in flavor profiles spoke volumes about his ability as a sommelier. Abandoning the typical American wine tasting service patterns that make wine seem buttoned up and stuffy, Mark lead us an informative journey covering the history of France’s wine regions, how each bottle is crafted, and does so with a candid sense of humor and lovely smile. He allows his guests room for thoughts and questions as they progress through a tasting filled with generous pours.

Portland is a true gem. If I lived in the northeast this would definitely be a location I would visit by train frequently. It’s walkable, charming, and the locals are an inviting, easy to love bunch of hard working people. There are so many destinations I did not get to see so I will be making a point to return.

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