This past weekend, I had the pleasure of teaming up with Passion Passport, Amtrak and my girlfriend/fellow photographer Ashley for a weekend of exploration, adventure and lots of eating in the seaside city of Portland, Maine.

We took a Friday evening train from the conveniently located North Station in Boston’s West End neighborhood. Having arrived a little early, we took advantage of the view of the Zakim Bridge while relaxing in Portal Park. We then headed into the station and quickly spotted the Downeaster Train. After hearing the announcement for boarding, we made our way to the track and quickly sat at a table in the cafe car.

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The ride to Portland is a little over two and a half hours, which gave us plenty of time to research more about the city. We hopped on the free wifi network and started surfing the web for places to see and restaurants to try. As we were sharing our findings with each other, a couple Portland natives in the next table couldn’t help but give us a few insider tips.

After getting an extensive list of recommendations, we decided to order drinks from the cafe and watch the light flicker in through the windows as the sun set over the passing marshes and towns. Before we knew it, we arrived at the quaint Portland Train Station. We then quickly headed to the hotel to drop off our luggage and grab dinner.

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Based on numerous recommendations, we made our way to Eventide Oyster Co. for dinner. We passed on getting a cab and decided to walk to soak in the city. When we arrived, we immediately found a spot at the bar and ordered a couple local beers. While everything on the menu was more than tempting, we both had to try the lobster roll made with brown butter served on top of a steamed bun. It was definitely the best bite we tried that weekend.

Realizing it was later than we thought, we headed back to the hotel to rest up for the early morning ahead of us. One of our friends was passing through town that night and agreed to meet us for sunrise at the picturesque Cape Elizabeth Lighthouse. The following morning, as we walked up the hill to the lighthouse we could see the sun was about to break over the horizon. We immediately rushed to the shoreline and began climbing the rocks to get the perfect vantage point.

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Having taken in the lighthouse from every possible angle, we made our way back to downtown to grab some much needed coffee. Our first stop was Bard Coffee, another obligatory visit to make when in Portland. After charging both our electronic and mental batteries, we walked a few blocks to Holy Donut for their famous potato donuts. The Dark Chocolate Sea Salt was beyond delectable.

After relaxing back at the hotel, we ventured out to grab lunch and see more of the sights. For lunch we ended up at Slab to split a slice of pizza. The slices were more like a thick doughy cloud topped with a light sauce and golden cheese. We then walked through the narrow streets stopping in and out of the unique boutiques on our way to Commercial Street. Along the water, we explored all the wharfs, admiring the numerous lobster pots stacked outside of the colorful fishing shacks. Wandering around in no particular direction, we found ourselves back at Eventide and convinced each other to split another lobster roll, because they are literally the best.

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As sunset approached, we met up with two friends we made through Instagram who had just moved to Portland. We discussed a few places to watch the sunset but decided to catch it along the Eastern Promenade Trail, a quiet stretch of rocky beaches along a windy walking trail and public park. After watching the sun fade into the horizon, we decided to grab some food at the highly recommended Duckfat. We were seated at one of the cozy outside benches which was perfect for the warm summer night. Ashley and I split the poutine and brisket sandwich, not leaving a crumb behind. The hype is real.

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We decided to take advantage of our last day in Portland by catching sunrise along the pier. As we walked through the streets we couldn’t help but notice how quiet and peaceful the streets were. Not a seagull for miles. Building up an appetite, we made our way to Becky’s Diner for breakfast. It was everything you would want and expect in an old New England Diner.

We then grudgingly made our way back to the hotel to pack for our train ride home. It wasn’t enough time to see everything. Arriving at the Portland Station, we headed right to the tracks and once again grabbed a table on the Café cart. The Downeaster train ride home was a little quieter as we both gazed over our pictures from the weekend, reliving the memories.

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Like any great weekend, it went by too fast. There was just too much to see and do. We received endless recommendations on places to eat and we quickly understood why. But what we found to enjoy just as much as the food was the casual seating which enabled us to take in the experience with those around us. While Portland might be a city, it felt more like a welcoming community full of those enjoying life at their own pace.

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Photos: Ashley McKinney and Brad Romano

Words: Brad Romano

Brad Romano and Ashley McKinney were invited aboard Amtrak to explore Portland through a partnership between Amtrak and Passion Passport. All opinions are their own. 

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Brad Romano
Brad Romano is a freelance travel and lifestyle photographer living in Boston. He has collaborated with number of companies including Beats by Dre, The Boston Globe, Heineken100, Hendrick’s Gin, Guatemala Travel and Tourism, and Verizon. Prior to pursuing his passion, Brad spent nine years as a Forensic and Litigation Consultant where he worked on cases involving insider trading, earning manipulations, money laundering as well as spending six months in Afghanistan investigating terrorist financing. To see more of his work, follow his journey on Instagram @bradromano.