Leeward
85 Free St, Portland
(207) 808-8623
Recent Reviews
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Our meals were excellent and the wait staff was pleasant and had great recommendations
Dietary restrictions: They offer homemade gluten free gnocchi as a substitute for most pasta dishes.
Atmosphere: 5
Food: 4
Service: 5
Excellent all around. I would describe the menu as Italian-inspired, given that their big thing is their homemade pasta, but it’s more of a modern menu as opposed to one of traditional Italian dishes.
For the starters: the gnocco fritto are a MUST-have. The roasted black salsify root was also fantastic - salsify root being a root veggie that’s something between a parsnip and a potato. That plate was practically licked clean.
For the mains: we went all pasta, though they do have a few larger “secondi” type plates. We had the sunchoke & goat cheese agnolotti (stuffed pasta), and the rigatoni with beef & pork ragù bolognese.
They had a good drink menu with a nice array of wines and cocktails, as well as nice mocktails.
For dessert, we had the plum sorbetto, as well as the best-dressed carrot cake I’ve ever had (topped with candied pecans, fresh blood orange, candied ginger, candied zest, rosemary).
We sat at the chef’s counter, which was amazing, because we got to see all of our food being prepared. We observed a super well-run kitchen, with staff seeming to be enjoying themselves, which made the food taste even better, as we were able to appreciate the effort put into it. It was also fun to see the other dishes on the menu being prepared and plated, plus being able to see what the most popular dishes were (the gnocco fritto was a common one, and for good reason).
The atmosphere and service were both great - our server was Molly.
Be prepared to spend (after tax & tip) upwards of $100 per person - note though that we ordered starters, mains, drinks, and desserts though, so quite a full sampling.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Gnocco Fritto
Delicious food and incredible service! 10/10
Atmosphere: 5
Food: 5
Service: 5
The food is pretty solid, we ordered the focaccia with balsamic with was phenomenal and then for entrees we ordered the butternut squash risotto and rigatoni with pork. I enjoyed both. I do wish there were a few more traditional Italian items on the menu but we were overall happy with our meals.
For dessert we had the butterscotch cranberry tart and the cinnamon apple gelato - both seasonal items I believe. Excellent, especially the gelato!
The bill for two was about $112. I don’t see myself becoming a frequent visitor but I’d definitely be interested in checking out the seasonal options in the future from time to time.
Staff were all lovely and friendly!
Wheelchair accessibility: No steps, spacious, accommodating!
Atmosphere: 3
Food: 4
Service: 4
Recommended dishes: Butternut Squash Risotto, Gelato, Rigatoni with Pork
Leeward thrives on a foundation of humble passion, expertise, and unwavering dedication to guest experience. Every team member shines, but Devin (spelling?) behind the bar truly stands out. Devin is among the most extraordinary hospitality professionals I’ve ever had the pleasure of meeting. Treat yourself to an unforgettable experience by requesting a seat at the bar and letting Devin guide you through the culinary adventure - simply hand over the menu and trust their impeccable choices. Say please and thank you, and be overly gratuitous at the conclusion of your experience - they deserve it. Thank you to the entire Leeward team for fostering such remarkable moments.
Atmosphere: 5
Food: 5
Service: 5
Came in several hours before our reservation and the Leeward team was happy to accommodate us at the bar. Ended up loving the bar team so much we stayed and enjoyed our entire meal there. Good food, great cocktails, even better service. Excellent gluten free options as well. Hope to be back soon!
Atmosphere: 5
Food: 5
Service: 5
Really good food with a couple stand out dishes (get the beef cheek ravioli). The best part was our waitress who was lovely and really enhanced our experience. Would be great if they added a couple more true vegetarian options.
Vegetarian options: Limited vegetarian options.
Atmosphere: 4
Food: 5
Service: 5
Recommended dishes: Ravioli
Really great food, well worth the trip. We dined here on a busy Wednesday night in the fall. Reservation was a must. Our appetizers were very good - a much lighter than usual focaccia and an extremely generous antipasto plate with large portions of prosciutto, sappressata, and burrata, and some wonderful fried gnocchi. The butternut squash risotto was excellent, cooked perfectly with complex layers of flavors. And the rigatoni with pork and beef bolognese was equally well prepared and super satisfying. Service was very good, and the prices were reasonable for this quality of the food. The only minor negative was that the dining room decor was a little bit stark. But the food was so wonderful that we won’t hesitate to eat here again.
Atmosphere: 4
Food: 5
Service: 5
Recommended dishes: Gnocco Fritto
An astonishingly good restaurant in every aspect — astonishing especially because every dish stands alone and yet converses charmingly with the ones that came before it. We arrived just after opening, without a reservation, and were immediately seated at the comfortable bar. The non-alcoholic cocktails are creative and delightful. We started with Brussels sprouts (the char… my goodness!) and moved on to two types of pasta that I had some doubts would complement each other, but as far as I’m concerned they were sheer genius. Dessert was ice cream that once again complemented everything perfectly, rounding out the meal without diminishing it at all (a so-so dessert can be a real sad trombone), and the Speckled Ax coffee was strong and delicious. Wonderful service, beautiful atmosphere (they use baffles! The sound quality is wonderful, a bubble of conversation), marvelous lighting, stylish staff… And a very reasonable check, to boot. I’ll be back here the first chance I get. Just an all-round terrific restaurant.
Atmosphere: 5
Food: 5
Service: 5
The food, atmosphere, and service were all outstanding. Literally every person who visited our table was genuinely so sweet and friendly. Food had great flavors and large portions. Highly recommend the arancini! When in Portland, try them out! But definitely make reservations because they had a line waiting to eat.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Arancini, Grilled Little Gem Lettuce Salad
Restaurantji Recommends
An incredible line up of delicious food! I cannot wait to come back again and try whatever this wonderful team thinks up next. Truly amazing ☺️
Atmosphere: 5
Food: 5
Service: 5
Is it possible that Leeward just keeps getting better? This place is a not to be missed culinary experience. I savored every bite of my meal, the cocktail and wine list is top notch, and the desserts don’t disappoint either. This is a must go.
Atmosphere: 5
Food: 5
Service: 5
I’ve always loved coming to this restaurant and usually visit a few times a year for special occasions. The food, drinks, and atmosphere are consistently great, but during my recent visit, the service was a huge letdown.
Our server was unfriendly from the start, greeting us with just “Want a drink?”—no warmth, no welcome. When we asked about specials, she smirked, shook her head, and sarcastically said, “They’re all special.” Throughout the evening, the service remained poor, and instead of enjoying our birthday celebration, we found ourselves discussing how uncomfortable the experience was and dreading her return to the table.
As someone who works in the restaurant industry, I understand that bad days happen, but this was beyond that. Oddly enough, we had better service at a dive bar earlier in the night. While I’ve had great experiences here in the past, this visit left us questioning if we’ll return.
Atmosphere: 5
Food: 5
Service: 1
We LOVE it here! Service, food and ambiance are great. We have been at least 15 times and have never left disappointed. Highly recommend for a special evening.
Atmosphere: 5
Food: 5
Service: 5
Very good food, great service and nicely set out restaurant
Atmosphere: 4
Food: 4
Service: 5
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