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

Tap on the wall behind Leeward’s bar, and you might hear the metallic jangle of antique sprockets and pulleys singing back to you.

If you’re brave (and have the bartender’s permission), set down your gorgeously balanced, Negroni-esque Polymorph cocktail ($15) and reach through the bottles of amaro, underneath the sparsely positioned floating shelves and the mix-and-match vintage wall art. If you’ve been nibbling on the spectacular grilled Broad Arrow Farm pork ribs with fried garlic and toasted flax seeds ($14), wipe your fingers off thoroughly, but then go ahead: Give the ochre-painted wall a firm rap with your knuckles. What’s that echo?

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

A relic of the space’s history as part of the Portland’s Porteous Building and the department store of the same name, the escalator remains, in chef/co-owner Jake Stevens’ words “entombed back there,” paused on its upwards journey toward the second floor.

While the couple understands the historic importance of the enormous machine, they’re in no hurry to rip down the wall. “Everyone has been trying to convince us to expose it, but it’ll cost a cool $80,000 to do that. So no, not right now,” Raquel Stevens added with a laugh.


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

Taken together, the eclectic décor weaves a homespun coziness across a cavernous dining area that was also once a textile classroom and a karate dojo. But a few questionable additions make the space feel a bit too improvisational – in particular, wall-mounted sound-dampeners that resemble upholstered headboards and a thrifted Tiffany-style pendant in the front window that looks like it belongs in a Swensen’s.

A server at Leeward brings food to a table. Brianna Soukup/Staff Photographer

Yet it’s hard to fault the duo for occasional missteps when you factor in their limited budget and the sheer scale of the boxy, featureless space. “We were really going for something inviting and contemporary without looking like it was done by a design firm,” Jake Stevens said. “We wanted to make it feel smaller, but the large size turned out to be a silver lining when we reopened during the throes of the pandemic, when space requirements were a big thing. We heard from a lot of people that it made them feel much safer having so much headspace and flow here.”

In 2021, I was one of those customers, although I didn’t have the option to eat indoors. Leeward, like most restaurants in Maine, tried its hand at takeout, then outdoor dining only on what must qualify as the nicest patio seating Free Street has seen in decades. Then early last autumn, Leeward reintroduced indoor seating, adding a vaccination requirement to create an indoor dining environment that, to this day, feels among the safest in Portland.

Yet, for a restaurant critic trying to maintain anonymity, showing a vaccination card at the host stand does pose a conundrum. Full disclosure: Staff did indeed figure out I was there, but according to Raquel Stevens, “If it’s any consolation, you really did surprise us.”

Jess Tamayo and Claire Griffin, both of Portland, dine at Leeward. Brianna Soukup/Staff Photographer

Another surprise that evening: It was new pastry chef Michelle Hicken’s debut dinner service. I had known that former Lio superstar Kate Fisher Hamm had planned to step away from Leeward to open Biddeford’s upcoming Fish & Whistle, but I thought I had a few more weeks to catch her in action; her golden, herby focaccia was one of the highlights of my 2021 takeout meals.


Fortunately, Hicken’s version ($6) was just as good: springy and light, featuring holes large enough to go spelunking in. And her take on a grapefruit tart ($11) also impressed. I loved the balance between the nearly savory, panna-cotta-like custard and the sticky dollop of sweet Italian meringue whipped to an impossibly smooth consistency. If there was a single intact grain of sugar left in that meringue, I couldn’t find it.

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

True. Leeward is a pasta restaurant. It’s undeniable that Jake Stevens makes excellent extruded, filled and hand-cut styles. If we stopped there, Leeward would max out any rating system I could create. But pastas need sauces, and during my recent visit, this section of the menu had both minor and major issues.

Creste di gallo with Calabrian chili sausage, left, and rigatoni with ragu Bolognese at Leeward. Brianna Soukup/Staff Photographer

Let’s start with the big one: The creste di gallo, a ruffled, semilunar pasta shaped like (and named after) a rooster’s crest. Dressed with house-made Calabrian chili sausage, caramelized fennel, chopped radicchio and a labor-intensive tomato conserva ($24), it had the makings of the sort of savory dish I’d normally crave, especially when you pour a puckery glass of off-dry Valle Reale Montepulciano ($13) to sip alongside. But this pasta dish was one of the saltiest plates of food I’ve eaten in years, so salty that I came close to breaking my own rule about not sending food back when I’m working on a review.

Less extreme, but still a bit too savory, was the rigatoni Bolognese made from a custom grind of cured pork products and grass-fed, grass-finished beef from North Carolina ($24). Perhaps it was the bitter harmonic flavors from sautéed dandelion greens (from Dandelion Spring Farms, naturally), or perhaps the brilliant method of finishing the dish with scalded milk that mellowed out the salt, but the equilibrium in this dish was touch-and-go.

Put those issues to the side for a moment. There are three words to explain why I have total confidence that Leeward’s team will correct 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 notorious for stealing the spotlight in any drink or recipe where it’s used. Its unsubtle, smoky flavor comes from charred stalks of rhubarb, and when this amaro is deployed in the slightest excess, it can make a cocktail taste like it’s being served in an old firefighter’s helmet. I’ve only ever been able to make it work when I add Sfumato drop-by-drop to a drink.

Chef and co-owner of Leeward Jake Stevens tops spaghettini pomodoro with olive oil before sending it out to a table. Brianna Soukup/Staff Photographer

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

“You’re kidding me!” I said. “Nope. It’s a full ounce,” Raquel Stevens told me. As we both sang Buehrer’s praises, she added, “I personally think it is the pineapple juice that does something magical to lift the drink.”

She’s right. That clear, tacit understanding of ingredients and balance is why I am certain that Leeward will reach its full potential, even though it’s not quite there yet. On sheer talent and perseverance alone, the restaurant, which was open for just a few days before the pandemic shut it down, survived two pandemic years. It’s easy to picture what success easier times will bring. You get the sense that, just like the antique elevator behind its walls, Leeward is on a trajectory that only leads up.

Andrew Ross has written about food and dining in New York and the United Kingdom. He and his work have been featured on Martha Stewart Living Radio and in The New York Times. He is the recipient of five recent Critic’s Awards from the Maine Press Association.

Contact him at: andrewross.maine@gmail.com


Twitter: @AndrewRossME

RATING: ***1/2

WHERE: 85 Free St., Portland. 207-808-8623. leewardmaine.com

SERVING: Tuesday to Saturday, 5 – 9 p.m.

PRICE RANGE: Appetizers: $9-$22; Pasta and entrees: $22-$37

NOISE LEVEL: Muffled teen sleepover


VEGETARIAN: Many dishes

GLUTEN-FREE: Some dishes

RESERVATIONS: Strongly recommended

BAR: Beer, wine and cocktails


BOTTOM LINE: Conceptually, Leeward fits right in with its fellow finalists for this year’s James Beard Foundation Award for Best New Restaurant. Chef Jake Stevens’ pasta-centric, eclectic Italian menu has some over-seasoning kinks to work out, but the kitchen’s strengths are on full display in dishes like sticky pork ribs sprinkled with nutty toasted flax seeds and a creamier take on Green Goddess dressing that I’d happily eat on any vegetable … perhaps even chicken and fish. Cocktails and moderately priced wines (most bottles clock in at around the mid-$50s) are also must-try items, especially the smoky, yet phenomenally balanced Italian on Holiday. Front-of-house manager Raquel Stevens leads the bar team as well as the friendly, knowledgeable servers who seem to love the place as much as locals and tourists do. “I’d come here on my day off if I could,” one server told me while depositing a plate of pillowy rosemary focaccia at my table. “This is my favorite place in the world.”

Ratings follow this scale and take into consideration food, atmosphere, service and value and type of restaurant (a casual bistro will be judged as a casual bistro, an 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 reviewer returns for a second. The reviewer makes every attempt to dine anonymously.

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