A Quintessentially Portland Day Trip

Window shopping on Exchange Street in Portland, Maine

My sister, Paige, has lived in New England for just over two years. I’ve visited in the dead of winter and for sunny summer trips through coastal Massachusetts towns. Last summer, we ventured a little further during my four-day stay in Salem.

Our first day, we enjoyed Salem’s Peabody Essex Museum and farmers’ market, along with a delicious charcuterie board (at Gulu-Gulu Cafe), at a leisurely pace. The next, we walked (miles) through Boston and Cambridge. We spent our last day laying on the beach in Beverly for an unseasonably warm June day.

The biggest adventure of our long weekend adventure was a quick trip to Portland, Maine. I hadn’t been to the city since a family vacation in the mid-2000s, long before I cared about good coffee, craft beer or Instagram-worthy lobster rolls. The drive from Salem to our first stop, Tandem Coffee Roasters‘ Congress Street location, was just over an hour and a half, making it an easy day trip.

Coffee at Tandem Coffee Roasters' Congress Street location

We enjoyed lattes and pastries alongside tourists and locals alike before heading down Congress Street to do some (very thorough) window shopping. The collection of shops lining the streets both downtown and in Old Port are the perfect combination of art galleries, curated collections and well-known favorites. After a couple of hours popping in and out of shops, we were ready for lunch.

Patio at Highroller Lobster Co in Portland, Maine

Lobster roll at Highroller Lobster Co in Portland, Maine

Our only meal in Portland had to be a lobster roll. We opted to split a lobster roll and a basket of fries on The Highroller Lobster Co.‘s colorful patio. While the frosé looked amazing, our next stop was East Bayside’s breweries.

We sipped on flights at Lone Pine Brewing Company‘s Portland tasting room and Goodfire Brewing Co. While the patio at Lone Pine was packed, walking around to the back of the building, where Goodfire is located, provided a much more relaxed environment, albeit with fewer options on draft.

Sunny patio at Lone Pine Brewing Company in Portland, Maine

Pint of beer at Goodfire Brewing Co. in Portland, Maine

The brewery-lined street is perfectly located for a walk along the Eastern Promenade Trail. And our walk just so happened to be at the same time as a puppy play date at East End Beach. We headed back to the car after a long loop through the neighborhood, ready for a snack-filled drive back to Salem.

View of sailboats from Eastern Promenade Trail in Portland, Maine

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