A great day in Maine inspired by Olive Kitteridge

I often treat the fiction section of The New Yorker as a preview of books to come based on excerpts in the magazine. This has been true with recent follow-ups from Lauren Groff and Curtis Sittenfeld, to name two favorites. These authors generally move into new territory, which is why I shot up in bed when Olive Kitteridge appeared in an August issue. A quick Google search revealed that Elizabeth Strout had written a second collection of stories about Olive, a strong-willed and complicated character, and the personalities inhabiting her small Maine town. The original earned Strout a Pulitzer Prize.

Fully awake, I rapid-fired texts to my mom and anyone else I knew who loved the novel. One of these friends had an advance copy of “Olive, Again,” and so I found myself with an unexpected gift this September. The collection, which hits shelves on Oct. 15, doesn’t disappoint as Olive grapples with identity, relationships, and death. Not only did it remind me how much there was left to learn about her, but also how much there was — for me as an outsider, at least — to learn about her version of Maine. Strout has been praised for her depiction of the state where she grew up and still has a home.

With Maine on my mind, I decided to take a road trip in honor of the book. Hearing this plan, my son, Graham, asked to skip school and tag along. My instinct was to say no, but then I considered Olive and her ongoing struggle to connect with her boy, Christopher. “The things that happen in childhood do not go away,” Strout writes in “Olive, Again.” Assuming that also includes the good things, which Graham has in abundance, I acquiesced. I recalled that keeping company becomes a salve for Olive as she combats loneliness in old age and wonders who she has been. Any mother can relate to that.

Because the coastal setting of Crosby is fictional, we’d start in Portland; in the first story, Jack Kennison, Olive’s second spouse, flees to the city for an afternoon. From there, we’d travel 26 miles north to Brunswick, where Strout spends some of the year with her husband, Jim Tierney. There’d also be a pit stop in neighboring Harpswell, a stamping ground of hers as a girl. The idea was to experience an approximation of Olive’s Maine and perhaps to gain insights along the way. I also wanted to experience the sunlight, which feels as essential to me as it does to Olive.

Following the two-hour drive to Portland, we parked on Commercial and strolled to the Highroller Lobster Co. for its namesake dish — like Olive, Graham enjoys his seafood — then back down Exchange toward the Portland Regency Hotel. It was one of those cloudless fall days where everyone carries on about the weather and basks in it such that the streets pulse with energy. This made the Regency’s Armory Lounge seem even darker — “the walls were dark green and the windows looked out at the sidewalks, but the sidewalks were high up in the windows, and mostly he could just see legs going by,” Strout writes of Jack.

We could also see rays filtering through the leaves on the trees outside, and though I wouldn’t normally pause for a day drink in a basement bar with my 10-year-old, I didn’t regret taking him to a place with a sign that implores, “Gentlemen, please remove your hats.” Over our Chardonnay and Sprite, we agreed that it merited a visit in winter, say February when Olive seems most taken with Maine’s light. For his part, Jack reflects on honesty and living an honest life, and we touched on that, too, in fifth-grade terms. If only all boys thought in those terms sometimes and didn’t wait until they were 74.

Brunswick beckoned, so Graham returned to reading in the back seat while I drove to the college town anchored by Bowdoin. There, we headed straight for Gulf of Maine Books. The shop, like Olive herself, is direct and fuss-free, with printer paper demarking the fiction section and a homemade “Dump Trump” sign. A stack of “Olive Kitteridge” sat on the counter where Gary Lawless perched on a stool and made small talk. Looking the part with a long white beard and glasses, Lawless has owned Gulf of Maine with his wife, Beth Leonard, for 40 years.

“The majority of our customers love Olive and want to know what’s next. She’s someone we know,” he explained. In Brunswick, I spotted multiple men wearing suspenders in a strictly utilitarian way and women with practical hairstyles gone gray. It’s the kind of northern place where students ride skateboards in Merrells and adorn their laptops with stickers proclaiming, “This Machine Kills Fascists.” In other words, people have opinions and seem real. “Here it’s Liz Strout land,” Lawless said of the author who’s also a patron, predicting, “We’re gonna have literary pilgrims from all over.”

These two pilgrims were hungry by then, having negotiated Graham’s book purchases down to two. Channeling Olive, who eats her fair share of doughnuts, we walked to Frosty’s, only to learn the local institution had already sold out. A tip sent us to the grocery store, which stocks the sweets, and we piled into the car for the short ride to Harpswell, parking at the end of Lookout Point Road. The tide was low, and Graham, belly full now, set about inspecting shells. “Thanks, mom,” he said with a smile, sun shining behind him. “This was a great day.” And I thought, what’s a good life but more great days than bad ones, and what’s a great novel but one that makes you appreciate them.

If you go . . .

“Oh, I love rides,” Olive says. So do we, particularly ones that involve food. In addition to eating lobster for lunch and our afternoon snack of doughnuts, we had happy hour at the Odd Duck FSE and dinner at Tao Yuan in Brunswick. The former shares attributes with the cavernous, new restaurant in the book and should satisfy steak eaters like Olive. The latter, with a James Beard-nominated chef in the kitchen preparing Asian small plates, is a destination in its own right.

The Highroller Lobster Co., 104 Exchange St., Portland, Maine, 207-536-1623, highrollerlobster.com

The Armory Lounge at the Portland Regency Hotel & Spa, 20 Milk St., Portland, 207-774-4200, theregency.com

Gulf of Maine Books, 134 Maine St., Brunswick, Maine, 207-729-5083

Frosty’s, 54 Maine St., Brunswick, 207-429-4258, frostysdonuts.com

The Odd Duck FSE, 11 Pleasant St., Brunswick, 207-844-8709, theoddduckfse.com

Tao Yuan, 22 Pleasant St., Brunswick, 207-725-9002, tao-yuan.me