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Informal Italian restaurant serving pasta, seafood & meat dishes, plus desserts & a large wine list.

At a glance

#5 of 93 Restaurants in Portland

LocalGuideWorld score: 4.77

4,073.2 km from the center of Portland

Rating breakdown

  • 5 ★91%
  • 4 ★5%
  • 3 ★1%
  • 2 ★0%
  • 1 ★3%
85 Free St, Portland, ME 04101, United States
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Quick facts

What is the rating of Leeward?
Leeward is rated 4.8 out of 5 based on 230 reviews.
How does Leeward rank in Portland?
Leeward is #5 of 93 Restaurants in Portland by LocalGuideWorld score (rating weighted by number of reviews).
Where is Leeward located?
85 Free St, Portland, ME 04101, United States — 4,073.2 km from the center of Portland.
How can I contact Leeward?
Phone: +1 207-808-8623 · Website: leewardmaine.com
Evan R
We came here for our 1 year wedding anniversary and this was an absolute hit. He drinks were delightful, and the food although mostly small plates was satisfying and they tasted amazing. We started with the house made focaccia before getting into our main dishes. I had the cod and sweet corn stuffed pasta and she had the tortellini with a mushroom sauce.
terri chau
Wonderful food, service and everything else. I went there twice in a week, that will tell you how much I like it. My friends that are from other countries loved it as well.
Daniela Olivera
Amazing dinner, cannelloni was so tasty, the half chicken was so delicious! Omg I would go back for sure. Drinks were also delicious. Perfect place for a great meal!
Stephy Miehle
Stunning meal! Yes, there was a wait for walk-ins, but the text waitlist was easy and efficient. We had ten minutes to head over and were a few blocks away, so it was no problem.

We enjoyed the cocktails (The Last Dandelion), mocktails (Palm Full of Rubies), and especially the focaccia — so airy and light, but perfectly rich with flavor. All of the pasta was so tender. The Bolognese wasn't my favorite version ever, but the pasta more than made up for that. Conversely, I wouldn't change a thing about the cannelloni; the bechamel sauce, creamy ricotta, and morels were all as lovely as the pasta. We also shared the grilled gem lettuce salad and olive oil cake; both were great and not too heavy with the rest of the meal. I'd happily come again to try more of the menu!
TJ K
It took us way too long to try this place but decided to make reservations before the summer tourist season is in full swing. First, it's a super cute establishment with a small cafe vibe. We started with the Foccacia. It was fantastic and large than it appears in images. We shared a salad for a starter (sorry it was so good we forgot to take a photo), I'm not a fan of green goddess dressing, and this salad made me love it. Finally, the main meal. We fully enjoyed the fresh pasta. The menu changes often, which makes it hard to recommend a dish. We'd say you can't go wrong with anything on the menu. Use Resy, make your reservation, and enjoy the freshest pasta in Portland!
Kaitlin Altieri
Leeward is a good date night spot. They have an intentionally small menu with fresh ingredients that make it hard to choose from! Fresh, upscale Italian food! Their staff are friendly, knowledgeable and accommodating. The open kitchen makes for a fun and upscale atmosphere. I will certainly go back, but save this place for special occasions. I would recommend making reservations and save time for parking. It’s kind of off the beaten path in Portland with no off-street parking. If you are there for a more casual occasion, sit at the bar by the kitchen so you can watch and smell all the delicious things the chefs are cooking up!
Deth Khaia
The bar seating are popular. As soon as they open at 5pm all the bar seating was taken and it's only Wednesday night. I highly recommended that you make reservation ahead. I was lucky to get a chef table seating. Food was good. Service is also fab. Definitely will go back and try their other dishes.
Sandy “The Boozy Foodie Lady” Anania
Leeward is a pasta-centric Italian restaurant in Portland, Maine.

The menu at Leeward changes seasonally, but it always features a variety of handmade pastas, as well as seafood, meat, and vegetable dishes. The ingredients are sourced from local farms and purveyors, and the dishes are cooked with a focus on technique and flavor.

The dining room at Leeward is small and intimate, with a warm and inviting atmosphere. The service is attentive and knowledgeable.

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