There’s a reason food lovers across New England keep pointing their GPS toward 85 Free Street in Portland, Maine — and it has everything to do with what husband-and-wife team Jake and Raquel Stevens built inside a beautifully converted former men’s department store in the Arts District.
Leeward is a 54-seat Italian-inspired restaurant where nearly everything on the table — from the focaccia to the fresh pasta — is made entirely in-house, and where the menu shifts constantly with the seasons to let the very best ingredients tell their own story.
It’s the kind of mom-and-pop restaurant experience in Portland, ME that makes you wonder why you’ve ever eaten anywhere else.
How Leeward Won Portland’s Hearts
Jake and Raquel Stevens opened Leeward in March 2020 — a famously terrible time to launch a restaurant — and yet, from the very first week of service, Portland’s food community leaned in hard.
The concept was immediate and compelling: an Italian-leaning menu anchored by handmade pasta in Portland, ME, and a commitment to seasonal, farm-to-table sourcing.
Local food forums declared Leeward “America’s Best New Restaurant,” and national food media began to take notice — a remarkable achievement for a small, locally-owned restaurant that doesn’t have the backing of a restaurant group or a celebrity chef.
The seasonal Italian menu rotates so regularly that regulars have learned to simply trust the kitchen, surrendering their habit of planning what to order before they even walk in.
The trust between kitchen and guest is the beating heart of what Leeward has built, and it’s the reason reservations disappear almost the moment they become available.
The farm-to-table dining in Maine movement has produced many worthy restaurants across the state, but few have managed to pair that philosophy with the technical finesse and genuine warmth that Leeward brings to every single service.
Food Highlights 🍽️
- Gnocco Fritto 🥙: A beloved Italian street food classic done right — light, pillowy fried dough —paired with cured meats, fresh cheese, and pickled vegetables.
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Focaccia 🍞: Baked in-house and served with olive oil — moist, perfectly salted, and nothing like the dry versions found almost everywhere else.
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Cured Pork Belly 🥩: Rich, deeply flavored pork belly — a small plate that’s also one of the most popular dishes.
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Squid Ink Pasta (Spaghettini Nero) 🦑: A squid ink spaghettini made with Rhode Island squid, serrano chile, and a restrained finish that lets fresh seafood take center stage.
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Bucatini 🍝: A spicy, lobster-forward bucatini fra diavolo built on a tomato base with large chunks of fresh lobster — bold, a little fiery, and completely addictive.
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Chicken Liver Mousse: Served with carte di musica — a paper-thin flatbread baked in-house — alongside a crab apple mostarda that adds a sweet, tangy counterpoint to the rich, salty mousse.
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Pan-Fried Skate Wing 🐟: Delicate skate wing finished in brown butter with a celery root remoulade — one of the kitchen’s most technically impressive plates.
- Rigatoni Bolognese 🍝: House-made rigatoni tossed in a slow-cooked pork and beef ragù with dandelion greens, delivering rich, satisfying comfort food.
Atmosphere ✨
Leeward occupies a beautifully converted former men’s department store in Portland’s Arts District, and the space carries that history gracefully — high ceilings, warm lighting, and a dining room that feels simultaneously celebratory and completely unpretentious. 🕯️
It’s large enough to host a milestone dinner but intimate enough that two people sharing a bottle of wine at the bar feel equally at home.
The wine list is extensive and thoughtfully curated, with servers who speak about each bottle with the kind of genuine knowledge and enthusiasm that turns a simple dinner into a full-blown education — and the creative cocktail program holds its own right alongside it. 🍷
For a mom-and-pop Italian restaurant in Portland, ME running one of the most ambitious seasonal menus in the state, the vibe is refreshingly relaxed — no stiff formality, no performative elegance, just great food, great wine, and a room full of people who clearly feel very lucky to be there. 🌟
Bottom Line
Why Leeward is worth every mile of the drive:
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🍝 Handmade pasta so good it’s been called some of the best in America
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🌿 A truly seasonal, farm-to-table menu that reinvents itself constantly
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🏆 A James Beard-worthy locally-owned restaurant with big-city craft and small-town soul
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🍷 An exceptional wine and cocktail program backed by genuinely knowledgeable staff
Address:
85 Free St, Portland, ME 04101
📞 (207) 808-8623
🕔 Open Tue–Sat, 5 PM–9 PM (closed Sun–Mon)