When the package arrived on my front porch last week, I didn’t recognize the sender’s name. Padded and light, about the length of a Scrabble tile rack, it could have contained one of several recent online purchases: cheesecloth, baker’s yeast, or a replacement for the sunglasses I mangled by running them through the washer and dryer … twice. Don’t ask.

Instead, I found a tangle of cloth masks I had ordered in mid-March. Cut from cotton overrun discarded by New York design studios, the masks appealed to my inner gambler. Every order is chosen at random, meaning you might receive a mask stitched from practically any fabric destined for a recent-vintage sofa, shirt, napkin or pair of curtains. I ordered an assortment of six.

Then New York and New Jersey were devastated by the pandemic, and one terse email in early April informed me that “Local demand means that your order might be significantly delayed.” In the meantime, I bought a few snooze-worthy green masks elsewhere and forgot about my original order – until last week made me the proud owner of a yellow chintz mask that I’m convinced was sewn from a fancy tablecloth. It is my new favorite thing.

My plan on this sun-soaked Saturday afternoon is to take my new mask out for a spin on a walk through downtown Portland, starting where new, planter-topped concrete barricades fence in a pedestrian-friendly stretch of Exchange Street. The blockade offers restaurants and bars a bit more outdoor real estate to help rekindle business as customers begin their cautious return to dining out.

That process may take some time. Not everyone is comfortable with visiting bars and restaurants yet – even when an al fresco option exists. Appetite for risk and anxiety is as important as appetite for a snack. These days, we have to consider both.

The Surf & Turf at Highroller Lobster Co. Carl D. Walsh/Staff Photographer

I say that while at the same time lifting the frame of my mask-fogged glasses to get a better look at the overstuffed Surf & Turf burger ($26) being devoured by of one of Highroller Lobster Co.’s patio diners. Seated at one of several vivid crimson picnic tables (a visual nod to the iconic furniture at Cape Elizabeth’s The Lobster Shack at Two Lights), she looks blissful. I get it. Before I leave, I send her a telepathic message: You might not think so, but you’ve still got room for a cup of the Old-Bay-dusted Highfries ($3).

She doesn’t seem to hear, so I move along, past Dobra Tea’s trio of outside tables – the restaurant calls them “Dobra Beach”– where bubble teas ($5.50-$5.75) and matcha cheesecake ($5.75) beckon, across the street to Eaux. Stretched along a cordon of rope at least as long as the slender profile of the restaurant’s interior are more than a half-dozen tables. Here, one of my most-missed dishes has made a sage-and-apple-strewn reappearance: crispy, sticky chicken & waffles ($15). I spot a black-masked server delivering an order along with a plate of the Johnny cake with mustard aioli and mushrooms, and I’m tempted to stop, but on this reconnaissance mission, I have miles to go before I sleep (or eat).

Bard Coffee’s take-out windows are one imaginative response to the pandemic. Gregory Rec/Staff Photographer

The bottom of the block is bookended by Black Cow, its customers spooning bites of caramel-drizzled tin roof sundaes ($8) as they relax in the shadiest part of Post Office Park, and a peek-a-boo “Walk Up Window” cleverly improvised through the side wall of Bard Coffee. I watch a young couple order sweet, milky Vietnamese iced coffees ($4) as I stand on the little mound of grass in Tommy Park.

From here, I’m distracted by a glint across the street and realize that it is the sun reflecting off the full protective plastic face shield worn by Gross Confection Bar’s host. The scene is at once a little disconcerting (this is the first time I have witnessed front-of-house staff in serious PPE) and comforting; Gross is taking this pandemic seriously, protecting its customers and staff alike. And did I mention the gallon pump-jug of hand sanitizer? If I were a furloughed server, I know where I’d want to work.

For nervous diners, Gross might also be a good place to dip a toe back into the water of dining out. Its sweet treat street cred is already well-established, with desserts like tender, seasonal strawberry cake with Speculoos crumble and dulce de leche ($4), but this year, Gross is also offering refreshing, summery cocktails like the peachy, vanilla-and-spice-scented Parasol ($11), as well as a lineup of more savory dishes, including a tart, peppery salad of arugula and local strawberries ($11).

Farther down the hill, things get a bit rowdier, especially on weekends. With Thirsty Pig’s picnic tables extending more than halfway across Exchange Street, and Blyth & Burrows and The Bar on the opposite side as you move down the street, this might be a stretch left to diners and carousers who have fully embraced reopening.

But if that’s not you, don’t let it stop you from dropping by Blyth & Burrows for one of their bottled to-go cocktails, especially the 5 Second Frenchie ($12), a balanced and invigorating sipper made with gin and aromatized white wine.

On the other hand, if revelry is what you seek, N to Tail’s exterior seating offers you a corner view of the buzziest part of the block, as well as aromatic sundubu ($7), a Korean tofu stew with shrimp and mussels, and one of the spiciest, crispest kimchi pancakes around ($15).

A lobster sign on the closed-to-vehicle-traffic Milk Street sits outside an al fresco dining area at Petite Jacqueline. Ben McCanna/Staff Photographer

The two-block stretch of pedestrian-only dining concludes at the bottom of the hill, but my stroll is not over. Now that aromas of restaurant cooking have begun to repopulate the air, I let my nose guide me whenever I can. Catching the scent of a grill in action (yes, even through my mask), it steers me left, toward the cobblestones. A few streets down, I spot a family sipping fruity, effervescent phosphates ($4.75-$6.75) under the umbrellas at Vena’s Fizz House, but my olfactory target is next door.

Nestled into black-and-white Eames-style scoop chairs on the brick sidewalk in front of Mami, a couple tucks into the dishes I smelled at least 100 feet away: grilled-beef gyudon donburi bowls ($13) and octopus-filled takoyaki balls ($8) served still sizzling, their bonito flakes fluttering on ripples of radiant heat.

I am tempted to stop but remember that tonight is my turn to make dinner. At home, a chuck steak from Wormell Farms in Cumberland has been luxuriating in a sous vide bath for the past hour. It is time I retrieved it.

Retracing my steps a bit, I turn this time and head up Market Street, where I pass Market Street Eats and reminisce about their Jose Cranseco ($9), a chicken salad sandwich slathered with cranberry mayonnaise. No matter the time of year, it always reminds me of Thanksgiving leftovers. At the corner of Milk Street, I look right and catch sight of the orange patio chairs at The North Point, where I foresee a glass of Burgo Viejo Rioja ($12) and a platter of Manchego, chorizo and wild boar salami ($23) in my near future.

Looking left, I’m equally enticed. Petite Jacqueline’s Milk Street exterior space comes the closest of any restaurant I’ve seen to replicating the charm of its interior. Adding to the appeal are, naturally, steak frites ($26) and a nose-tickling poutine seasoned with fines herbes ($10).

The chalkboard at the newly coined Camp Hunt + Alpine details the rules for dining during the pandemic. Ben McCanna/Staff Photographer

One last detour beckons before I leave the Old Port. The steak I’ve got bubbling away could use a preamble, so I order to-go cocktails from Portland Hunt + Alpine Club, where they have branded their deck-like, Market Street parklet as “Camp Hunt + Alpine.” On the chalkboard, you’ll find the fictitious camp’s hygiene and safety rules, including the most important: “Listen to your camp counselor.”

I’m only visiting as a day camper, so I collect my minty Whiskey Smash ($18/ two servings) and fiery, Mezcal-fueled Bonecrusher ($18/two servings). “I love your mask,” the server says as she brings me my bag. “Where did you get it?”

I smile. Then realizing she can’t see the lower half of my face, I shrug instead. “It’s a long story,” I reply.

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 three recent Critic’s Awards from the Maine Press Association.
Contact him at: andrewross.maine@gmail.com
Twitter: @AndrewRossME