Portland, Maine is about a 2-drive from Boston, and one of our favorite New England destinations. It is close enough for a day trip, and great for a weekend getaway. Although Portland is smaller than Boston, the food is good, the people are friendly, and it is enjoyable in winter as well as in summer. Known for lobster, you can certainly find this summer New England favorite here, but also fresh seafood, donuts, coffee, ice cream, treats, and happy hour specials.
We spent part of President’s Day weekend (just about 24 hours) in Portland and revisited many favorite spots, and discovered a couple of new ones. I know that we will be back, so pin/save/bookmark this post for updated recommendations!
Stop in to the Press Hotel for a drink at Inkwell that you can enjoy by the cozy fireplace with a book or magazine, play a board game, and take in their homage to news and type executed tastefully throughout the decor (I’m one to appreciate a nice hotel lobby with character), or brunch at UNION next door.
For views of Portland, including nice water views, the Top of the East, located inside the Westin Hotel, is a great spot to take in the views, relax, and enjoy an appetizer, such as a nice cheese plate and a drink. I went with a blueberry mule, because, when in Maine, enjoy the blueberries!
Dine at Miyake for a nicer sit-down meal of Japanese cuisine, or take the brood to Street & Co for the freshest seafood in a place full of character. Enjoy your dinner on copper tables and under the dried herbs, onions, and shallots that no doubt make it onto the plates. Pro Tip: on the day-of, get in at 4:50 pm to put your name down for a 5:30 seating or see if they have later availability.
Eventide Oyster Co. recently arrived to the Fenway neighborhood in Boston, but before that, we’d often put our name down at Duckfat, where everything is cooked in – you guessed it, duck fat – and have an appetizer at Eventide Oyster Co (a delicious hot lobster roll and some raw oysters). 
The letters on the wall at Duckfat are one of my favorite parts that set the scene. They’re known for their fries – also cooked in flavorful – you guessed it, duck fat. It’s a popular spot we like to take out-of-town visitors to!
Not feeling like seafood? Get a taste of Mexico at Taco Escobarr.
Pop in to Gelato Fiasco for tasty ice cream at its source (you can find pints of it in Boston, but it isn’t easy). I gravitate towards the blueberry pie flavors!
Parlor Ice Cream is currently based in Portland and you can find their unique flavors incorporated in their support-local scene – I found it at a new and fun spot to us, The Highroller Lobster Co, started in 2017. I’m happy we found this casual eatery that specializes in all things lobster. I love the red-white decor and ’50’s diner feel with the red counter stools and booths, which made it feel like summer even though it was snowing outside. I heard they often do have a wait.
If you love donuts, you have to try The Holy Donut for Maine’s Potato Donut.
Snag a pie at Two Fat Cats or Standard Baking Co to take home.
Coffee and coffeeshops are more my scene, so we go to Bard Coffee every time and sit by the window to read, rest, and chat. The back half of the shop is a nice place to catch up on emails, sit with a few people, and write or work. Monday nights, they also have Makers Night, where crafters can bring their knitting, sketches, or other creative work to the communal table to make with some company from 5-7 PM.
Tandem Coffee Roasters beans can be found in Boston at different cafes (I have seen it at Espresso Yourself in Jamaica Plains), but the original is in Portland. We visited the roastery, and enjoyed a savory scone and a warm cup while making new friends.
For shopping, located across from Bard Coffee, Blanche & Mimi is a sweet spot for home gifts and cutest gifts for children. Browse Bliss for leather, denim, fashion, and Judith for chic women’s fashion and jewelry. Stonewall Kitchen – gifts for foodies, elevate your own home cooking with sauces, dressings, mixes, jams – also try the classes and the tent sales in the summer in nearby town of York for discounts! There’s good shopping nearby (the 24-hour L.L. Bean & outlets) for an afternoon jaunt, with an only 30-min drive to the nearby towns of Kittery and to Freeport.
If you’re staying the weekend, there’s a large Whole Foods and Trader Joe’s, as well as smaller organic neighborhood grocers where you can pick up what you need.
Whether you arrive in Portland by train, plane, or automobile, you’ll leave full with so many great eats! We’ve enjoyed our visits in every season. I hope you do too – send me a postcard when you go to let me know what you tasted and explored in Portland, Maine ;).
Happy adventuring!
