Friday
Evening
History and art

When we arrive outside The Francis, it’s raining, and an eighteenth-century–style chandelier guides us past the puddles and through the front door. My boyfriend, Kelsey, and I warm up next to the front parlor fireplace before we are greeted and shown to our room.

The Francis hotel, located on Congress Street, is named after architect Francis Fassett, who built it in 1881 as a home for Mellen E. Bolster, a prominent dry goods dealer. After a two-year renovation project beginning in 2016, the Francis is now on
the National Register of Historic Places. Our room overlooks the back courtyard and has two queen-size beds along with a few pieces of modern furniture that complement the giant black-and-white photographs that line the walls.

Despite the heavy rain, we attend Creative Portland’s First Friday Art Walk before our dinner reservation. As we make our way down Congress Street toward the vendors outside the Maine College of Art, we stop to meet painter Rhonda Pearle at Bridge Gallery and to see installations at Space, a nonprofit gallery and event space.

Inside Maine Oyster Company, we find a large display of unshucked oysters over a bed of ice. Originally just a small oyster farm in Phippsburg, Maine Oyster Company opened its restaurant and raw bar in the heart of West Bayside in October. We sit at the counter and watch as the team of shuckers prepares us a dozen local oysters on the half shell. We pair them with house-made mignonette sauces and two glasses of prosecco on draft.

Saturday
Morning

The rain has subsided into a gentle mist, making for a refreshing walk to breakfast. It’s 11 a.m. when we grab the last two open seats at the counter at Local 188. Sipping on hot green tea and black coffee, we wait for our mushroom herb scramble and corned beef hash. After brunch, we stop by the Francis to put on another layer of sweaters, then walk across the street to Tandem Coffee and Bakery—a gas-station-turned-cafe bustling with West End locals.

Afternoon
Rainy-day respites

With hot apple ciders from Tandem in hand, we find cover from the rain at Yes Books—a rare and used bookstore next to Congress Square Park. Inside, hundreds of books are tucked into floor-to-ceiling bookshelves, making the tightly packed space feel like a maze. It is a respite for any book lover on a rainy day.

The walk through Portland is cozy in the early November fog. We make our way through the yellow leaves in Tommy’s Park, along the cobblestone streets of the Old Port, and eventually up Congress Street toward Washington Avenue. Our first stop on Washington’s up-and-coming foodie strip is Oxbow Brewing Company, where we sit at wooden barrels and drink the flagship Farmhouse Pale Ale. Next door to the brewery is Maine Mead Works, where I try honey wine for the first time. My favorites are the iced tea flavor and the dry “ultimate modern” mead.

One of the restaurants adding to the popularity of Washington Avenue is Drifters Wife, a stylish wine-focused eatery that was ninth on Bon Appétit’s 2018 list of America’s Best New Restaurants. I meet my parents at the bar for a glass of natural wine and tapas before the dinner rush. Nearby is Cong Tu Bot, a hip Vietnamese noodle shop that opened in 2017. Outside, the wind is howling, and we make our next and final stop on Washington for a hot tea and a bowl of pho.

Evening
Bowling lanes and Japanese cuisine

We take a cab to Bayside Bowl, which is packed with casual bowlers as well as professional leagues. Since the lanes are first-come, first-served and it is
7 p.m. on a Saturday night, our chances of getting one are slim. However, there is a bar in the far back of the alley, so we meet up with two friends from the area, order craft beers, and watch people bowl before we head into the Old Port for dinner.

The sign outside Miyake is lit up with white florescent lights that catch our eye as we step out
of the cab. Inside, we are seated at a table near
the floor-to-ceiling window that looks out onto Fore Street. Chef Masa Miyake, who was a finalist for the James Beard Foundation’s Best Chef in the Northeast award, runs the restaurant. Miyake cooks traditional Japanese cuisine and draws upon seasonal flavors as well as Maine’s local seafood selections. We take our time with the menu before deciding on two bowls of miso soup with Maine-harvested mushrooms, omakase nigiri (a chef’s selection of sushi), kamo aburi-binchotan (grilled duck breast), and a large house salad to finish.

After dinner we walk to Wharf Street, a cobblestone road that’s home to some of Portland’s favorite night spots. Later we stop at Maps, an underground bar decorated with vinyl records and vintage maps; Amigos, a Mexican restaurant and bar; and Gritty McDuff’s, where Gabe Tonon, a guitarist from Nashville, is playing Johnny Cash during last call.

Sunday
Morning
West End flow

It’s almost 10 a.m., and the yoga class at Hustle and Flow is filling up. I place my mat next to the window so I can feel the morning sun while I do my poses. After class, I stroll through the streets of the West End and back to the Francis.

Kelsey and I meet for brunch in Bayside at Isa Bistro, where brick walls and tin ceilings make us feel like we are dining in true metropolitan style. We order eggs Benedict and rabbit hash with arugula and fried eggs. After brunch I drive to the Eastern Promenade to walk along the park and enjoy the ocean views.

Afternoon
Island destination

Since Two Fat Cats Bakery is only a three-minute walk from the Casco Bay Lines ferry terminal, I stop to buy a slice of blueberry pie and tea before hopping on the ferry to Peaks Island. Once on the island, I walk along New Island Avenue toward Picnic Point to photograph the foliage and island houses. As the sun sets and the sky turns to gold, I head to the beach to find a quiet place to sit and watch the sun go down before heading back to the mainland.

Evening
Ferry views

The Portland skyline lights up the harbor as we make our way past Fort Gorges. I find a seat inside the ferry, cozy up next to a window, and relax at the end of my busy weekend in the city.