Leeward

The gist: Husband and wife duo Jake and Raquel Stevens (chef and front-of-house maven respectively) cut their teeth at nationally acclaimed restaurants, including Beast in Portland, Oregon and Drifter’s Wife in Portland, Maine before opening Leeward. The food: Stevens roots his Italian-inspired, pasta-centric menu in tradition while incorporating seasonal ingredients in deliciously fun ways. Start with a burrata, citrus, and pomegranate salad, accented with earthy taggiasca olives, fresh mint, and pistachio aillade (a light garlic and nut emulsion) before tucking into ricotta gnocchi with trumpet mushrooms, arugula, and black truffle conserva, or ribbon-shaped mafaldine bolognese.

With its warm ochre walls and homey bookcases stashed with dried bouquets and books, Leeward is the embodiment of just the kind of mom-and-pop-gone-perfectionist restaurant that Portland excels at. Paige Buehrer and owner Jake Stevens—she oversees the wine; he runs the kitchen—have rendered it a darling of food fiends across the state and country (among its accolades are multiple James Beard finalist placements). And for good reason: For all of the other luscious dishes here (Maine scallop crudo with ginger and grapefruit, for one; chicken liver mousse with bacon and chokeberry mostarda, for another), it’s the handmade pastas that steal the show.

Housed in what was once a men’s department store in downtown Portland, Leeward is a contemporary, Italian restaurant where, like a good suit, everything is tailor-made. Almost the entire menu is prepared and baked in-house, whether that’s the focaccia or carte di musica that accompanies their homemade chicken liver mousse. You can’t go wrong here with any of their constantly rotating shareable plates like salty, crispy artichokes and butter-poached radishes.

With nods from critics far and wide, Leeward is one of the state’s most celebrated restaurants. This high-ceilinged, Italian-centric restaurant turns out exquisite handmade pasta like the spaghettini Nero laced with squid, serrano chile, pork brodo, white wine, and bread crumbs—a revelation of flavors both strong and soothing.

If you’d like to dine at Leeward this autumn, you’ll have to check the weather first. According to co-owner Raquel Stevens, intense breezes during colder months have a tendency to turn Free Street into a bit of a “wind tunnel.” So before you make any plans to dine at one of the pasta-centric, modern Italian restaurant’s 16 sidewalk patio seats, check the forecast. “We’ll keep the patio open throughout October at least,” Stevens told me. “But we’ll also just have to keep our eyes on the skies to make sure the weather cooperates!.

Along with Fore Street, Leeward is another must-try upscale dining establishment that's known for its pasta-focused menu. If seafood is all you're after, hit up Eventide Oyster Co., which boasts an extensive oyster bar in addition to a la carte seafood dishes, including its signature brown butter lobster roll and the revered New England clam bake. The Shop at Island Creek Oysters serves up outstanding bivalves, raw seafood and local brews in a fun, casual setting.

Leeward skips the pageantry and gets straight to the good stuff: pasta that doesn’t try too hard, starters that punch above their weight and a wine list that backs up the ambition. Current menu highlights include rye cavatelli with braised rabbit and fennel, spaghettini nero laced with squid and serrano and sacchettoni stuffed with pork sausage and ricotta. If you’re not into pasta, the pan-fried skate wing with brown butter and celery root remoulade doesn’t miss.

Housed in what was once a historic men’s department store in downtown Portland, Leeward is a pasta-centric restaurant where, like a good suit, everything is tailor-made. Almost the entire menu is made and baked in-house, whether that's the focaccia and crackers, fresh pappardelle that’s filled with slowly braised beef cheeks, or the well-balanced desserts. The dining room is spacious and warm, making it the perfect place for a special occasion.

Leeward opened in March 2020, just a couple days before it had to shut down due to COVID. When it reopened several months later, it quickly earned accolades, including a James Beard nomination for Best New Restaurant and The New York Times 2022 America’s Best Restaurants list. After a visit with a large group of friends, I understand why!

Leeward is a newer Italian in the Old Port that just opened in 2020. But it’s already making a name for itself, having been nominated for a national award for Best New Restaurant. This popular, trendy newcomer on the Portland Maine restaurant scene serves Italian favorites like bucatini, roasted duck breast, tagliatelle, and more.

Two other Mainers were also up for awards last night, including Jake Stevens of Leeward for Best Chef Northeast and Woodford Food & Beverage for Outstanding Hospitality, both in Portland. Best Chef Northeast this year went to David Standridge of the Shipwright’s Daughter in Mystic, Connecticut.

Leeward, which a number of pros name-checked for its stellar natural wine selection, has raked in accolades since the moment the restaurant threw open its doors, and deservedly so. All of their fresh pastas are out-of-this-world, but you’d be remiss to overlook the gnocchi fritti appetizer.

Jake Stevens of Leeward on Free Street represented Maine among the nominees for Best Chef in the Northeast category. The win went to David Standridge of The Shipwright's Daughter in Mystic, Connecticut.

Best Chef: Northeast – Celia Bruns, Artemisia Cafe; Ian Driscoll, Bar Futo; Valerie Goldman, The Honey Paw; and Jake Stevens, Leeward