Saturday 

Noon

After parking by Taproot Market (and stopping in to buy a new copy of the crafty magazine), I venture toward Munjoy Hill, a walk dotted with dozens of great shops, galleries, and coffee joints. Entranced by the bright colors of his geometric designs, I’m drawn into the pop-up shop of Portland-based artist Ebenezer Akakpo. “I’m hopeful that this will become a permanent store,” he tells me. “I’ve been really happy here so far.” Akakpo guides me through the symbolism of his different patterns, each based on ancient Ghanaian symbols. I leave with a tumbler decorated with an apple green filigree-esque pattern that means “hope.” I plan to use it as a vase for my newly hatched daffodils. 

I make my way across Washington Avenue to visit the Black Box, a retail space made from shipping containers that was designed to house small businesses and recent start-ups. I get a coffee at Moonday Coffee while browsing the small selection of 14-karat gold necklaces and earrings by Rebecca Perea-Kane (her line, inspired by nature, is called Thicket Jewelry). I dip into Alice Yardley Maine and find the leather worker’s dad behind the register for the day. After discovering that I have a daughter, he points out a special flower handbag Yardley created for her niece. It’s embellished with a leather daisy. “For her birthday,” he suggests. 

On my way up the hill I stop in at Plant Office to admire the lush greenery and clever merch. I don’t need a new houseplant, but I find myself tempted by the pale pink leaves of a stromanthe. 

2 p.m.

The Portland Observatory makes an easy landmark for navigating the city—not to mention that it’s an interesting historical structure in its own right. The 86-foot-high tower on Munjoy Hill served as a communication station for Portland’s bustling harbor from 1807 until 1923. I decide to walk down Congress Street toward LB Kitchen (they have the best turmeric lattes in town). On the way, I stop to browse the rare books at Carlson and Turner Books and Bookbindery, shop the vintage fashions at Ferdinand, and check out the avant-garde works at Dunes gallery. I buy a paperback at Print: A Bookstore before stopping to admire the brick facade of Etz Chaim Synagogue. Normally, I’d stop in to see the collection of contemporary Maine art housed in its first-floor gallery—or at least to enjoy the peaceful garden—but seeing as it’s Saturday, the temple is occupied. Next time! 

3:30 p.m.

After checking in at my accomodations, Blind Tiger Portland, I meet my husband and daughter at Deering Oaks Park. The playground is full of kids, and as Juniper flies down the zipline, I look around the grounds. Since the late 1800s, this park has served as a “public breathing space” for Portlanders, and recent renovations have only improved its utility. Today we stick to the kids’ area, but there’s also a pretty duck pond, a Victorian duck house, a sweet little castle, and plenty of walking trails. 

5 p.m. 

Garrett and Juniper have to get back to our dog, so we stop in at Local 188 for an early dinner of gnocchi and mussels. We play “I Spy” with Juniper while we wait for our food, admiring the colorful oil paintings by Holden Willard that adorn the brick walls. 

7 p.m. 

I decide to take a walk around the city before bed and find myself stopping in at the Jewel Box for a solo drink. I haven’t been to this spot in years, but it’s precisely as fabulous as I remember, with campy Victorian aesthetics and a young, cheerful crowd—perfect for people watching. 

Sunday

7 a.m.

The best part of staying at Blind Tiger on Carleton Street is, without a doubt, having a breakfast of fresh bread with Nutella and berries and terrifically strong, dark coffee in the sitting room. While the bedrooms are lovely and well appointed, the shared areas of the house are gloriously busy, decked out with antiques, comfortable furniture, and stocked with big, beautiful coffee table books from Rizzoli and Princeton Architectural Press. There’s something to look at in every corner and, later, plenty of places to sit and nurse your drink. 

8:30 a.m.

After breakfast, I decide to spend some time walking around the West End neighborhood admiring the spring flowers—fragrant lawns of bluebells! sunny daffodils! blushing magnolias!—and playing a personal game of spot-the-plaque. Many of the buildings on Bramhall Hill date back to the nineteenth and early twentieth centuries, and quite a few of them have been lovingly preserved, which makes my stroll feel pleasantly like a quick trip to the Victorian Era. I stop to take pictures of the gothic arches and angles that adorn the John J. Brown House and the funky brown detailing on the A.B. Butler House. 

Soon enough, I need another coffee. Although Tandem on Congress Street (cleverly located in a former gas station from the 1960s) is packed to the gills, I still venture inside for a scone, since no one does savory–sweet quite like them. 

11 a.m. 

I decide to give my Portland Museum of Art membership a workout, flashing my red card at the entrance before walking past the gift shop and sculpture garden to the rotunda. I’m here to see the photography exhibition that has just opened, Outside the Frame: Todd Webb in Africa. The photographs were commissioned by the United Nations Office of Information and show midcentury life in nine countries, from Ghana to Kenya. 

Noon

Before driving home, I make a quick stop at the University of New England Art Gallery. The 1970s building is often called “the little jewel” for its sweet size and general preciousness. It only takes a few minutes to browse the small museum, which houses renowned works by Winslow Homer and Isamu Noguchi, but as always, I enjoy the quiet and beauty of this overlooked space.