Leeward Leeward
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  • Leeward


    85 Free St, Portland, ME 04101, United States


  • Leeward


    +1 207-808-8623


Service options

+ Dine-in

+ Delivery

Highlights

+ Great cocktails

+ Great dessert

+ Great wine list

Popular for

+ Dinner

+ Solo dining

Accessibility

+ Wheelchair-accessible entrance

+ Wheelchair-accessible seating

+ Wheelchair-accessible toilet

Offerings

+ Alcohol

+ Beer

+ Cocktails

+ Coffee

+ Comfort food

+ Small plates

+ Spirits

+ Vegan options

+ Vegetarian options

+ Wine

Dining options

+ Dinner

+ Dessert

+ Seating

+ Table service

Amenities

+ Bar on site

+ Gender-neutral toilets

+ Toilet

Atmosphere

+ Cosy

+ Romantic

+ Trendy

+ Upmarket

Crowd

+ Tourists

Planning

+ Dinner reservations recommended

+ Accepts reservations

+ Usually a wait

Payments

+ Credit cards

+ Debit cards

+ Credit cards

Children

+ High chairs

Parking

+ Paid multi-storey car park

+ Paid street parking

+ Parking


Leeward menu

Grass-Fed Ny Strip Steak, Lentils, Grilled Broccolini, Cacio E Pepe Butter

US$32.00

Butternut Squash Raviolo, Egg Yolk, Brown Butter, Sage

US$21.00

Gigli, Maitake Mushrooms, Tomato Passata, Olive Crumble

US$20.00

Saffron Malloreddus, Smoked Lamb Ragu, Collard Greens, Rosemary

US$25.00

Mafaldine, Beef & Pork Bolognese, Dandelion Greens, Parmigiano-Reggiano

US$22.00

Sweet Potato Agnolotti, Oyster Mushrooms, Prosciutto, Cream, Horseradish

US$20.00

Whole Wheat Tagliatelle, Melted Leeks, Fennel, Stracciatella, Cured Egg Yolk

US$20.00

Chicken Liver Mousse, Crab Apple Mostarda, Carta Di Musica

US$14.00

Full Menu

Discover Leeward

If you're ever in Portland, Maine, and looking for a cozy spot that offers a delicious meal with a relaxed atmosphere, Leeward should definitely be on your radar. Located at 85 Free Street, this charming diner is quickly becoming a local favorite for both residents and visitors alike. Whether you're stopping in for a quick bite or planning a leisurely meal, Leeward provides a welcoming space that combines great food with a warm, inviting vibe.

One of the standout features of Leeward is its thoughtfully curated menu. The restaurant has a knack for combining classic diner fare with fresh, innovative twists. Whether you're craving a comforting breakfast or a hearty lunch, there’s something on the menu to satisfy all tastes. For example, the classic diner-style eggs and bacon are prepared to perfection, with crispy, golden edges on the bacon and eggs cooked just right, whether you prefer them scrambled or sunny-side up. On the other hand, the more adventurous eaters can opt for dishes like their signature Avocado Toast, topped with perfectly poached eggs, arugula, and a drizzle of lemon vinaigrette. The combination of flavors makes this dish a standout and a favorite among regulars.

In addition to the wonderful food, the service at Leeward is exceptional. The staff is friendly, attentive, and eager to make your dining experience enjoyable. I’ve visited on multiple occasions, and each time, the staff has gone out of their way to ensure everything runs smoothly. Whether it’s offering recommendations from the menu or refilling your coffee without having to ask, it’s clear that customer satisfaction is a top priority.

The ambiance of Leeward plays a big part in its charm. It has a laid-back, almost nostalgic vibe that makes you feel right at home. The diner’s interior features a mix of modern touches and retro-inspired décor, giving it a cozy, inviting atmosphere that’s perfect for both casual meals and intimate gatherings. The open kitchen concept also adds a unique touch, allowing diners to watch the chefs work their magic. It's a fun experience, and it adds to the overall sense of connection to the meal you're about to enjoy.

Another reason to check out Leeward is its commitment to using fresh, locally-sourced ingredients. Many of the dishes incorporate ingredients from local farmers and artisans, which not only supports the community but also ensures that everything on the menu is as fresh as possible. This focus on quality ingredients is evident in the flavors of the dishes. For example, the house-made pastries are a perfect way to start your day. Freshly baked and paired with a hot cup of coffee, they’re an indulgence you won’t soon forget.

Another thing worth mentioning is the range of options on the menu. Whether you’re a vegetarian, vegan, or a meat lover, there’s something for everyone. The Leeward Veggie Burger is an excellent choice for those who prefer plant-based options, with a hearty patty made from a mix of lentils, quinoa, and roasted vegetables, topped with avocado and tangy house-made sauce. For those who enjoy a more traditional meal, the sandwiches and burgers, especially the classic cheeseburger with bacon, are always a hit. Pair any meal with their delicious house-made fries, and you’ve got a winning combination.

In terms of its location, Leeward benefits from being situated in the heart of Portland, making it an easy stop whether you're a local or just passing through. The diner is not only conveniently located, but it’s also close to a variety of other attractions in Portland, such as the Portland Museum of Art and the scenic Old Port district. After enjoying a satisfying meal, you can easily take a stroll through the charming streets of Portland and explore the city.

What makes Leeward particularly special is its ability to deliver both quality food and a memorable experience. It’s not just about eating; it’s about enjoying your time in a comfortable, friendly environment where the focus is on good food and great company. Whether you’re visiting for the first time or you’re a regular, Leeward consistently delivers in terms of both flavor and atmosphere.

For anyone visiting Portland, ME, Leeward is a must-try. From its delicious and innovative menu to its exceptional service and cozy ambiance, it’s easy to see why this restaurant is gaining such a loyal following. Whether you're in the mood for a classic diner breakfast, a creative lunch option, or simply a place to unwind with friends, Leeward has something to offer everyone.


Leeward Photos

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Location & Contact

Get in touch with our support team


  • 85 Free St, Portland, ME 04101, United States
  • +1 207-808-8623




Clock


Hours

Our open schedules

Day
Monday Closed
Tuesday 05:00 PM - 09:00 PM
Wednesday 05:00 PM - 09:00 PM
Thursday 05:00 PM - 09:00 PM
Friday 05:00 PM - 09:00 PM
Saturday 05:00 PM - 09:00 PM
Sunday Closed



Reviews

  • Leeward was such a delightful treat! Reservations are recommended as they fill up fast. We loved their flavorful and fun mocktails. The menu is small and constantly updated based on what is in season. It made it easy to decide what to order. For appetizers we got the focaccia and fried artichoke hearts. The focaccia was soft and balanced with a saltiness that paired beautifully well with the olive oil. The artichokes were tender and lightly battered. I ordered the mushroom ricotta pasta and my husband ordered the braised rabbit pasta. This place is known for their pasta dishes and did not disappoint! My favorite dessert was the hazelnut tart. We had such a good time overall. Service was efficient, the waitstaff was prompt and helpful, and we left having had a perfect amount of food for a fun night out. I highly recommend Leeward!

    Audrey D
  • We really enjoyed our dining experience here. The host and server were great, our server made some great recommendations such as the gnocchi dish which was AMAZING, the best I’ve ever had. The fig salad and lobster sphegettini were lovely as well.

    Kira “NYC foodie”
  • Wow! What an amazing experience! The atmosphere is warm and welcoming from the moment we were greeted. Maddy, our server, was such a pleasure! And we do hold that high on the list of important aspects of dining out, which we do a lot. Then came the drinks from the menu which were soooo delish! And oh the fooood Everything we ordered was perfection!

    Victoria Hernandez
  • EDIT: Adding more to my original review having returned to Leeward more than once - it is a top restaurant in Portland. This time around, the order included the sacchettoni, the halibut, and some exceptional asparagus. Oh, and the gnocco fritto, *always* ! ORIGINAL REVIEW: 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.

    Chad Klinefelter
  • This is our second time coming here and it was absolutely exquisite both times. We had the squash bloosom apatizer.Fried in the lightest of batters it was so good. Between that and the two house made pasta dishes we had we moon with flavor and deliciousness. If your in portland check this place out, you wont be disappointed.

    Chris Hamilton
  • Leeward was outstanding. I had "fusilli, black trumpet mushrooms, corn crema, caramelized shallots, radicchio, lemon thyme".. The corn crema sauce was quite subtle distinctive and lovely.The Waitress explained it had mascarpone in the sauce which made it rich without being goopy My wife had "cannelloni, sheep’s milk ricotta, chanterelle mushrooms, parmigiano-reggiano" – also excellent and very different in flavor from mine For dessert I had panna cotta with chocolate sauce and fresh figs brulee. It was wonderfully earthy, not sweet, with layers of flavors. Came back again 5/6/25. Another wonderful dinner here (which I chose for my birthday). The surprise highlight was an unforgettable "savoy cabbage salad, anchovy-horseradish vinaigrette, pecorino, purple daikon, seeds & grains". Amazing texture and taste.

    James Stephen Shaw
  • Leeward is a must stop restaurant any time we are in Portland. The menu is delicious and the chef does an excellent job of highlighting the season. They do a great job with gluten free, offering gnocchi as a substitution that is just as good as the regular stuff. We'll be back!

    Emily Palmer

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Leeward

Discover Leeward at 85 Free St, Portland—a cozy spot serving fresh, flavorful dishes with a creative twist. Perfect for food lovers seeking a memorable dining experience!

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