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Leeward
Italian
Warm ochre walls, bookshelves stacked with dried flowers, and handmade pasta that regularly lands a James Beard nomination: this cozy Italian restaurant on Free Street is the kind of neighborhood spot that somehow becomes a national conversation. The chef's shapes and sauces pull from whatever local producers are doing well right now, and the wine program is its own reason to linger. Settle in and watch Portland's Arts District do its thing out the window.
The awards strongest first
- James Beard Awards 2022 · Nominee · Best New Restaurant
- James Beard Awards 2024 · Nominee · Best Chef: Northeast · Jake Stevens
- Wine Enthusiast Forward 50 Restaurants
- The New York Times The Restaurant List
- Condé Nast Traveler 15 Best Restaurants in Portland, Maine
- Eater The 15 Best Restaurants in Portland, Maine
- Portland Press Herald Best 75 places to eat and drink in Greater Portland
- James Beard Awards 2022 · Semifinalist · Outstanding Pastry Chef · Kate Fisher Hamm
- James Beard Awards 2026 · Semifinalist · Best Chef: Northeast · Jake Stevens
- James Beard Awards 2025 · Semifinalist · Best Chef: Northeast · Jake Stevens
One number, weighted & current 88
How we scoreThe dishes from the writeups
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Maine scallop crudo
“For all of the other luscious dishes here (Maine scallop crudo with ginger and grapefruit, for one”
Condé Nast Traveler -
Chicken liver mousse
“chicken liver mousse with bacon and chokeberry mostarda, for another), it’s the handmade pastas that steal the show.”
Condé Nast Traveler -
Beef and pork ragu Bolognese
“Find respite from the notoriously windy section of Free Street at aptly named Leeward, where gorgeous plates of Maine scallop crudo and beef and pork ragu Bolognese have made this pasta haven a fast favorite.”
Eater
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The neighbors closest first
- Arcadia Eat · 52
- Asmara Eat · 65
- Regards Eat · 72
- Another Round Eat · 52
- Room for Improvement Cocktail Bar Drink · 83
- Speckled Ax Eat · 52
- Artemisia Cafe Eat · 61
- Friends & Family Neapolitan Pizzeria Eat · 52
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