This Is One Of The Best Maine Restaurants To Try In 2026 If You Love Fresh Pasta

A plate of fresh pasta can make an ordinary Tuesday feel like a special occasion, especially when the noodles are made by hand. Portland, Maine, has an Italian restaurant that takes this seriously, serving seasonal dishes inside a former department store with a fascinating past.

What caught my attention was the combination of old-fashioned craftsmanship and a menu that never stays quite the same. The pasta might arrive with a rich, slow-cooked sauce one evening and something completely different a few weeks later.

Even the building has a few surprises, including an old escalator concealed behind a wall. The restaurant has earned national recognition, but the handmade food is the real reason to visit.

A Historic Department Store

Long before anyone twirled a single noodle here, 85 Free Street sold suits and ties as a men’s department store connected to the Porteous Building in downtown Portland, Maine. That retail history still shapes the room today, giving Leeward a roomy 5,000 square feet with soaring ceilings and huge floor-to-ceiling windows.

The space feels a lot like a European brasserie, with generous proportions and plenty of breathing room between tables. Exposed ductwork overhead adds an easy, modern edge, while warm lighting keeps the whole place feeling snug once the sun goes down.

Decor leans toward what could be called family-room chic. Thrifted finds and a mix-and-match collection of vintage wall art cover the walls, so every corner has something fun to look at while waiting for food.

Here is the quirkiest detail of all. An antique escalator, left over from the old store, sits entombed behind the bar like a museum piece nobody wanted to throw away.

Although the old escalator remains hidden behind a wall near the bar, its unusual history makes for a great conversation starter on a date. Few restaurants can claim their bar is guarded by a retired staircase that once carried shoppers between floors.

Handmade Pasta Every Single Day

Flour, eggs, and patience are the real stars at Leeward. Every day, the kitchen makes its pasta and bread from scratch, and that commitment sits at the very center of what this restaurant does.

The menu is Italian-inspired rather than strictly traditional, which means familiar shapes often show up with a creative Maine twist. Past dishes have included Saffron Malloreddus with smoked lamb ragu, collard greens, and rosemary, plus simple Tonnarelli tossed with fresh pomodoro, basil, and garlic.

Seafood fans have plenty to smile about too. Squid Ink Spaghettini has paired squid with pickled chiles and cherry tomatoes, while Taglierini Nero has combined squid, pork brodo, chili, and crunchy breadcrumbs.

Because the pasta is cut fresh, the texture is springy and tender with a pleasant bite that dried noodles simply cannot match. Sauces cling to every ridge and curve, so each forkful carries plenty of flavor.

A smart move for newcomers is ordering two or three pastas for the table and sharing. Portions are satisfying without being overwhelming, which leaves room to sample more shapes and sauces in one visit.

Think of it as a tasting tour where every stop involves a different noodle.

Rigatoni Bolognese And Other Signature Plates

Some dishes earn a permanent spot in your memory after one bite, and the Rigatoni Bolognese is a strong candidate. Made with a combination of beef and pork, the ragu cooks low and slow until the flavor turns deep and rich.

Wide rigatoni tubes catch the sauce inside and out, and dandelion greens add a slightly bitter freshness that balances the meatiness. A snowfall of Parmigiano Reggiano finishes it off with a salty, nutty kick.

For something lighter, Sheep’s Milk Gnudi are a delight. These ricotta-like dumplings are poached until they feel almost cloud-soft, then served in a pool of brown butter and sage that smells like a cozy autumn kitchen.

Another showstopper has been the Butternut Squash Egg Yolk Raviolo. One large pasta pillow hides a golden yolk, and it arrives with delicata squash rings, brown butter, and crispy fried sage leaves.

Cutting into it is half the fun, since the yolk spills out and becomes part of the sauce. Because the menu shifts often, any of these could be swapped for a new creation, so ask your server what the kitchen is excited about that night.

Starters Worth Showing Up Early For

Picture a warm square of golden, dimpled focaccia landing on the table, still fragrant from the oven. That house-baked bread is often paired with carta di musica, paper-thin Sardinian crackers that shatter with a satisfying crunch.

Gnocco Fritto is a must for anyone who loves a little indulgence. Puffy fried-dough pillows come with prosciutto, fennel salami, and a creamy globe of burrata, so every bite mixes crisp, salty, and silky all at once.

Chicken Liver Mousse might sound bold, but it is smooth, lightly sweet, and surprisingly easy to love. It is usually served with crackers and a tangy crab apple mostarda that brightens each scoop.

On the fresher side, the Scallop Crudo features Gulf of Maine scallops with lemon puree, purple daikon, almonds, and chervil. When scallops are out of season, bluefin tuna steps in as a worthy stand-in.

The ‘Nduja Toast is another fun pick, layering spicy spreadable pork sausage on thick sourdough with tart pears, honey, and almonds. Small plates have ranged from about $6 to $28, so building a starter spread for the table is easy and lets everyone try a little of everything.

A Menu That Follows The Maine Seasons

Ever notice how a tomato in August tastes nothing like one in February? Leeward builds its whole menu around that idea, changing dishes often, sometimes even daily, to match what is freshest.

Maine-grown produce, regional meats, and local seafood fill the plates. A Beet-and-Citrus Salad might arrive with mint leaves, fried capers, and anchovy salsa verde, while a Savoy Cabbage Salad shines with an anchovy-horseradish vinaigrette.

Desserts follow the calendar too. Past sweets have included carrot cake, panna cotta, and a savory cheesecake with watermelon, husk cherries, and a hint of fennel.

One summer treat was a Brioche Maritozzo filled with lemon zabaione, local strawberries, basil, and meringue. It is the kind of dessert that tastes like a sunny afternoon at the farmers market.

Gluten-free guests are well cared for here. A house-made ricotta gnocchi can be swapped into most pasta dishes, and several starters and entrees can be adjusted as well.

Because the lineup keeps rotating, no two visits are quite the same. Coming back in a different season feels like discovering a brand new restaurant hiding inside a familiar one, which is a pretty great excuse to return.

Warm Service From A Husband And Wife Team

Behind every great dining room is a team that makes guests feel at home, and Leeward is run by owners Raquel and Chef Jake Stevens. Raquel leads the front of the house, while Jake runs the kitchen, and both bring experience from acclaimed restaurants on the East and West coasts.

Service here feels warm and genuine rather than stiff or showy. Staff members know the menu inside and out, often describing dishes with the confidence of people who understand exactly how they were made.

The pace of a meal is relaxed on purpose. Nobody hurries guests out the door, so lingering over a final bite of dessert or a long conversation feels completely natural.

Raquel also curates a list of around 50 mostly Italian, low-intervention wines, and the team offers thoughtful non-alcoholic choices too. Asking a server for a suggestion is a simple way to find something new to sip with dinner.

The open kitchen adds even more personality. Seats at the chef’s counter offer a front-row view of cooks rolling, boiling, and plating, which is honestly better entertainment than most TV cooking shows.

Kids and grown-ups alike tend to find it fascinating.

Prices, Hours, And Pasta To Take Home

Good news for budget planners: Leeward keeps things clear and fair.

A full evening with starters, pasta, drinks, and dessert can top $100 per person. For the quality of handmade food and the care behind each plate, the value feels solid and well earned.

Dinner is served Tuesday through Saturday from 5 PM to 9 PM. The restaurant is closed on Sundays and Mondays, and it sometimes takes short breaks or hosts private events, so checking ahead before driving over is a smart idea.

Here is a bonus many visitors miss. The Pasta Provisions program lets guests bring Leeward home, with cook-at-home pastas like cavatelli and gnocchi priced around $7 to $14.

Sauces, cheeses, and gelato are also available to go, usually between $6 and $10. Grabbing a kit makes a great souvenir from Portland, and it beats a keychain by a mile.

For bigger celebrations, Leeward offers private events, including family-style dinners for 20 to 44 guests. Special rates apply for Sunday and Monday gatherings.

Smart Tips For Landing A Table

Did you know Leeward was a finalist for Best New Restaurant at the James Beard Awards in 2022? That kind of national spotlight means tables fill up fast, so a little planning goes a long way.

Reservations open on Resy at 9 AM, exactly 30 days before the date you want. Setting a phone alarm for that morning is a clever trick for snagging a prime weekend slot.

Spontaneous diners still have a shot. Bar seats are held for walk-ins on a first-come, first-served basis, so arriving right around the 5 PM opening gives the best odds.

A few policies are helpful to know. Cancellations need four hours of notice to avoid a $20 per guest fee, and there is a fifteen-minute grace period for anyone running late.

Larger groups should know that separate reservations will not be combined. Babies and children also need to be counted in the party size, since space is planned carefully.

Fun fact to share at the table: the word leeward means the side sheltered from the wind. With its calm pace and cozy glow, the name fits this Free Street spot perfectly.