Leeward is a nautical term meaning “sheltered from the wind,” but the owners of Leeward, a new Italian restaurant on Free Street in Portland, have seen their share of stormy weather in their first year of business. The restaurant’s opening last March coincided with the first confirmed case of COVID-19 in Maine. The restaurant had four nights of dinner service before closing for what owners Jake and Raquel Stevens thought would be only a few weeks but ended up being nine.

Leeward weathered the first wave of the pandemic, staying busy with takeout orders and preparing meals for Cooking for Community, a nonprofit that raises funds for restaurants to prepare boxed meals for Portland’s vulnerable populations. Jake calls his participation in the program “one of the only bright spots” to have come from the pandemic.

Jake and Raquel moved to Maine in the summer of 2017 from Portland, Oregon, with the goal of eventually opening a restaurant of their own. The two are longtime restaurant workers; after culinary school, Jake gained experience in the kitchens of high-end restaurants in Portland and Los Angeles while Raquel waited tables and honed her wine knowledge. The Stevenses say their experiences in a variety of restaurants shaped their own, leading them to eschew pretense and an autocratic kitchen style for a more collaborative and empowering approach. After moving to Portland, Jake and Raquel scored jobs at two of the city’s most acclaimed restaurants, Eventide Oyster Co. and the now-closed Drifters Wife, to “get the lay of the land” and develop relationships with the farmers, fishermen, and other purveyors of local foods with whom they now work.

Leeward’s menu is made up of several small plates and entrees of handmade pasta. An appetizer of ’nduja toast—a thick slice of sourdough bread that is spread with a layer of spicy North African sausage, topped with thinly sliced tart pears, and finished with a drizzle of honey and chopped almonds—is rich and complex. A plump ball of burrata cheese comes artfully surrounded by roasted apples, slices of purple radish, crisp crostini, and toasted pecans. Perfectly charred stalks of broccolini nestle on a rich bed of buttery lentils that delivers an unexpected depth of flavor.

The pasta dishes are a riot of shapes and textures: slick black strands of squid ink spaghettini, long ruffly strips of mafaldine, and chewy trumpet-shaped gigli. Each pasta shape complements its sauce, capturing bits of rich beef and lamb Bolognese or delicately encasing a dollop of cheesy butter-nut squash filling. But Jake says he doesn’t hew too closely to the traditional Italian pairings of pasta and sauce: “I think fighting against dogma was a very important thing to us, in all facets of this restaurant.” Rather, he is inspired by what grows best in Maine and the ways he can let the ingredients shine.

Raquel puts just as much thought into her wine program. The list of 49 primarily Italian wines ranges from lesser-known varieties like dolcetto and freisa to traditional favorites like nebbiolo and sangiovese. Raquel seeks to “match the integrity of the [wine] producers” with the standards of the Maine farmers they work with. This can mean vintners that farm organically, use wild yeasts, and eschew additives in their wines—techniques that fall under the loose label “natural wine.”

Cocktails at Leeward are similarly thoughtful. A short craft cocktail list from bar manager Caroline Richter reads like a farmstand Mad Libs. Bourbon infused with porcini mushrooms comes together with fresh ginger juice, coffee bitters, and sugar in Woods Wise, a fall-inspired take on an old-fashioned. The Thornback recalls the warming flavors of holiday dinner with smoky mezcal spiked with hot peppers, unsweetened cranberry juice, mole bitters, and an orange peel syrup. A small number of local beers on tap rounds out the selection of alcoholic beverages.

In late October, as cooler weather settled in, Raquel and Jake broke down the street-side patio they had used over the summer and once again set up the dining room for service. Just as they were beginning to cautiously host a steady stream of indoor diners, the number of local coronavirus cases began to increase. Despite the many precautions they’d taken, the Stevenses decided indoor dining didn’t feel right, so they reverted back to offering takeout only. “It’s complicated,” Raquel says. “But the most important thing to us is the safety and well-being of our staff and ourselves and our guests.”

Raquel and Jake plan to open Leeward again for indoor dining when it feels less risky. Whether their dishes are enjoyed via takeout box in the comfort of your home or in the restaurant’s spacious dining room on Free Street, the inventive small plates and pasta dishes from Leeward are sure to g respite from the stresses of the day.

Leeward
85 Free St., Portland
207.808.8623
leewardmaine.com

Refined small plates and handmade pastas using seasonal ingredients. Beverage options include Italian wines from small and innovative producers, Maine craft beers, and inventive cocktails.
Small plates $5–$14
Entrees $20–$30

The Space
Leeward’s dining room was once the men’s department of Porteous, Mitchell, and Braun Company, the historic department store that operated from 1904 to 1991, and was more recently a part of neighboring Maine College of Art.

Hours
Takeout and packaged pasta, sauces, and cocktails are available to-go.
Lunch: Friday and Saturday, 11:30 a.m.–2 p.m.
Dinner: Thursday through Saturday, 5 p.m.–9 p.m.