Dine Out Maine: Despite occasional missteps, plenty to savor in Leeward

Editor’s note: Leeward is closed for a break until May 5th.

Tap on the wall behind the Leeward bar, and you might hear the metallic clank of antique cogs and pulleys answering you.

If you’re brave (and have the bartender’s permission), lay down your beautifully balanced Negroni-esque shapeshifting cocktail ($15) and squeeze through the amaro bottles, under the sparsely positioned floating shelves and the vintage mix-and- art game. If you’ve nibbled on Broad Arrow Farm’s spectacular grilled pork ribs with fried garlic and toasted flaxseeds ($14), wipe your fingers down carefully, but go ahead: give the ocher painted wall. What is this echo?

“It’s the oldest escalator in Maine,” co-owner and manager Raquel Stevens told me.

A relic of space history as part of Portland’s Porteous Building and the department store of the same name, the escalator remains, in the words of chef/co-owner Jake Stevens “buried there”, stopped in its upward journey to the second floor.

While the couple understand the historic significance of the huge machine, they are in no rush to tear down the wall. “Everyone tried to convince us to exhibit it, but it will cost $80,000 to do it. So no, not now,” Raquel Stevens added with a laugh.

It’s surprisingly easy to imagine what removing that wall might do to the mostly Italian, pasta-focused restaurant. The Stevens’ design acumen occupies territory that borders on 1970s-inspired eclecticism fully realized, with cork wallpaper, skinny white barstools and a bespoke tchotchke-filled hutch that bisects the dining room. . So really, what’s an extra escalator or two?


Taken together, the eclectic decor weaves a cozy vibe into a cavernous dining room that was also once a textile classroom and karate dojo. But a few dodgy additions make the space feel a little too improvised — in particular, wall-mounted sound absorbers that look like upholstered headboards and a Tiffany-style pendant in the front window that looks like it belongs in a Swensen.

A Leeward waiter brings food to a table. Brianna Soukup/staff photographer

Still, it’s hard to fault the duo for occasional missteps when you consider their limited budget and sheer scale of the square, featureless space. “We were really looking for something inviting and contemporary without looking like it was done by a design company,” said Jake Stevens. “We wanted it to feel smaller, but the large size proved to be a silver lining when we reopened during the throes of the pandemic when space needs were great. Many people have told us that it makes them feel much safer to have so much free space and flow here.

In 2021 I was one of those customers, even though I didn’t have the option to eat inside. Leeward, like most restaurants in Maine, dabbled in takeout and then alfresco dining only on what must be considered the prettiest patio Free Street has seen in decades. Then early last fall, Leeward reintroduced indoor seating, adding a vaccination requirement to create an indoor dining environment that to date feels among the safest in Portland.

Yet for a restaurant reviewer trying to remain anonymous, showing a vaccination card at the host’s booth poses a conundrum. Full disclosure: The staff did indeed realize I was there, but according to Raquel Stevens, “If it’s any consolation, you really surprised us.”

Jess Tamayo and Claire Griffin, both from Portland, dine at Leeward. Brianna Soukup/staff photographer


Another surprise that night was the first dinner service from new pastry chef Michelle Hicken. I knew former Lio superstar Kate Fisher Hamm had planned to move away from Leeward to open Biddeford’s next Fish & Whistle, but I thought I had a few more weeks to see her in action; his golden herb focaccia was one of my 2021 takeout highlights.

Luckily, Hicken’s version ($6) was just as good: springy and lightweight, with holes big enough for caving. And his version of a grapefruit pie ($11) also impressed. I loved the balance between the almost savory, panna-cotta-like custard and the sticky dollop of sweet Italian meringue whipped to an incredibly smooth consistency. If there was a single grain of sugar left intact in this meringue, I couldn’t find it.

I did however find sand elsewhere during my meal. The background texture of incompletely rinsed greens isn’t a meal killer for me, but it’s certainly not enjoyable, especially not when the rest of the dish – a salad of buttered lettuce with crumbled blue cheese and a tarragon, lemon adjacent to Green-Goddess, chervil and chive vinaigrette ($11) – was otherwise terrific. “Well, it’s not a salad restaurant,” my guest joked.

True. Leeward is a pasta restaurant. There’s no denying that Jake Stevens makes great extruded, filled, and cut styles by hand. If we stopped there, Leeward would maximize any scoring system I could create. But the pasta needs sauces, and on my recent visit this section of the menu had minor and major issues.

Creste di gallo with Calabrian chili sausage, left, and rigatoni with Bolognese stew in Leeward. Brianna Soukup/staff photographer

Let’s start with the big one: the crest di gallo, a fluffy semi-lunar pastry shaped like (and named after) a rooster’s crest. Dressed in homemade Calabrian chilli sausages, caramelized fennel, chopped radicchio and a labor-intensive tomato preserve ($24), it had the makings of the kind of savory dish I would normally crave, especially when you pour a glass of Valle Reale Montepulciano off-dry puckery ($13) to sip on the side. But this pasta dish was one of the saltiest plates I’ve eaten in years, so salty I almost broke my own rule of not sending food back when working on a review.


Less extreme, but still a tad too tasty, Rigatoni Bolognese made from a custom grind of cured pork products and grass-fed, grass-finished beef from North Carolina ($24) . Maybe it was the bitter harmonic flavors of sautéed dandelion greens (from Dandelion Spring Farms, naturally), or maybe it was the brilliant method of finishing the dish with scalded milk that sweetened the salt, but the balance in this dish was touch-and-go.

Put those questions aside for a moment. There are three words to explain why I have complete confidence that the Leeward team will fix lingering seasoning issues as soon as they read this: Amaro Sfumato Rabarbaro.

A gruff, herbal liqueur from the Trentino-Alto Adige region of northern Italy, “Sfumato” is known to steal the show in any drink or recipe it’s used in. Its unsubtle, smoky flavor comes from the charred rhubarb stalks, and when this amaro is rolled out to the slightest excess, it can make a cocktail taste like it’s been served in an old fire helmet. I’ve only ever been able to get it to work when I add Sfumato drop by drop to a drink.

Leeward chef and co-owner Jake Stevens tops spaghettini pomodoro with olive oil before sending it to the table. Brianna Soukup/staff photographer

At Leeward, bar manager Paige Buehrer mixes Sfumato into the Italian on Holiday cocktail ($12) with pineapple juice, lime and Angostura amaro. When I inquired about the amounts used in this phenomenal and nuanced daiquiri-like concoction, I expected to hear “a dash” or “1/8 oz,” but not a full Sfumato jigger.

“You’re kidding!” I said. “No. It’s a full ounce,” Raquel Stevens told me. As we both sang Buehrer’s praises, she added, “I personally think it’s the pineapple juice that does something. magical thing to elevate the drink.”


She’s right. This clear and unspoken understanding of ingredients and balance is why I’m sure Leeward will reach his full potential, even if he’s not quite there yet. Thanks to his talent and perseverance, the restaurant, which was only open a few days before the pandemic closed, survived two years of the pandemic. It’s easy to imagine the success that easier times will bring. You get the sense that, much like the ancient elevator behind its walls, Leeward is on a trajectory that only goes up.

Andrew Ross has written about food and restaurants in New York and the UK. He and his work have been featured on Martha Stewart Living Radio and in The New York Times. He recently received five Critics’ Awards from the Maine Press Association.

Contact him at: [email protected]

Twitter: @AndrewRossME


OR: 85 Free Street, Portland. 207-808-8623. leewardmaine.com


PORTION: Tuesday to Saturday, 5 p.m. to 9 p.m.

PRICE SCALE: Appetizers: $9 to $22; Pasta and appetizers: $22 to $37

NOISE LEVEL: Smothered teen slumber party

VEGETARIAN: many dishes

GLUTEN FREE: Some dishes

RESERVATIONS: Highly recommended


BAR: Beer, wine and cocktails


BOTTOM LINE: Conceptually, Leeward fits right in with his fellow finalists for this year’s James Beard Foundation Award for Best New Restaurant. Chef Jake Stevens’ eclectic, pasta-centric Italian menu has some seasoning flaws to work out, but the cuisine’s strengths are on full display in dishes like sticky pork ribs dusted with hazelnut-roasted flax seeds and a creamier version of the Green Goddess dressing which I would happily eat any vegetable…maybe even chicken and fish. Moderately priced cocktails and wines (most bottles sell for around $50) are also must-have items, especially the smoky but phenomenally balanced Italian on vacation. Front desk manager Raquel Stevens leads the bar team as well as the friendly and knowledgeable waiters who seem to love the place as much as the locals and tourists. “I’d come here on my day off if I could,” a waiter told me as he brought a plate of fluffy rosemary focaccia to my table. “It’s my favorite place in the world.”

Ratings follow this scale and consider food, ambience, service, value and type of restaurant (casual bistro will be judged as casual bistro, expensive upscale restaurant as such) : * Poor ** Fair *** Good **** Excellent ***** Extraordinary. The Maine Sunday Telegram visits each restaurant once; if the first meal was unsatisfactory, the examiner returns for a second. The reviewer goes out of his way to dine anonymously.

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