People love to ask me where to eat, especially in the summertime. Friends, casual acquaintances and strangers email nearly every week when the weather turns sunny and warm. By and large, the requests take a familiar form: “I’m coming to Portland. What should I try when I’m there?” Before we went into our extended coronavirus hiatus, I’d scribble a few personalized suggestions and copy-paste a link to my Best 75 Restaurants in Greater Portland rundown from 2019. But as you might have realized, things have changed.

We’ve lost more than 10 percent of the businesses in that article — a tally that could have, probably should have, been much worse. Lucky for us, we have also seen some excellent new restaurants open. Pandemic be damned.

This year, I’m taking the bull by the horns and proposing a gastronomic weekend getaway to appeal to visitors and locals alike. My food-fueled itinerary includes indoor and outdoor options for lunches and dinners to accommodate those of us who might not be ready to dine inside just yet.

Remember: During their recovery phase, many restaurants continue to be financially fragile and short-staffed, so whether you’re a Mainer or “from away,” book a table in advance, be kind, and above all, tip as if your next Vacationland meal depended on it.

Judy Gibson’s Welcome Back cocktail Photo by Stephanie Perkins/Courtesy of Judy Gibson



When chef/owner Chris Wilcox (Eventide, Velveteen Habit) opened Judy Gibson in South Portland early last year, he couldn’t have anticipated that he’d serve dinners for two short weeks before the pandemic lockdown forced him to close until summer. In the interim, he managed to keep his business chugging along on sheer optimism and takeout orders of fried chicken. A little over a month ago, Wilcox was finally able to ditch the comfort food and reopen Judy Gibson as the smart, New American bistro he always envisioned.

Grab a two-top along the red banquette and order a Welcome Back cocktail ($12) to start. A perky, effervescent sipper made with gin, ginger, St. Germain elderflower liqueur and a sparkling wine float, it’s an ideal drink to celebrate Maine’s gradual reopening as you nibble on spicy tuna crudo with whipped tahini ($15). Welcome back, indeed.


Bayside’s Wilson County Barbecue had a bit more runway than Judy Gibson, but barely. Open two months before COVID restrictions took hold, this North Carolina-inspired barbecue joint never stopped serving, even when things looked dire. Once outdoor dining was allowed again last summer, Wilson County BBQ’s ample, sheltered patio became a destination for displaced Southerners, and it remains every bit as enticing today, thanks in no small part to the restaurant’s specialty: vinegary, Carolina-style pulled pork ($19).

Wilson County Barbecue’s pulled pork sandwich Photo by Nicole Wolf/courtesy of Wilson County Barbecue

Perhaps better still are the restaurant’s snacks and side dishes, like whiskey-kissed hushpuppies ($7) and batter-dipped, crisp-fried okra ($7). Both match well with the Smokin’ Daly ($12), a Ketel One Peach house-made iced tea and smoked lemonade cocktail that calls to mind a pitcher of sweet tea garnished with juicy stone fruit.


As long as you’re up and about before noon, head to South Portland’s Omi’s Coffee Shop for coffee, house-made pastries and savory snacks. My favorite is the Italianesque, vegetarian-friendly Green Goddess breakfast sandwich ($8.75): a split, toasted English muffin filled with cheddar cheese, a fried egg, garlicky pesto, avocado and pickled red onions. If sweet is more your speed, you can’t go wrong with Omi’s impossibly layered, square-cut blueberry biscuits ($3.50) dripping from every side with melted honey butter.

Norimoto’s Strawberry Tart Photo courtesy of Norimoto

And while you’re in SoPo, place an online order from Atsuko Fujimoto’s Norimoto Bakery. You won’t find a more seasonally inspired baker anywhere, so try one of her rotating selection of fruit tarts and Danish, or a babka striated with sweet adzuki bean purée ($9.50).


Jackrabbit’s curried egg salad sandwich with trout roe Photo by Bowman Brown/Courtesy of Jackrabbit


Get out of town and head south to Biddeford. You might expect that I’d send you to the freshly renovated Palace Diner – and to be fair, I wouldn’t blame you if you end up there. But your actual destination is one of the many new businesses repopulating the once-languishing Pepperell Mill. Here, where Main Street builds to a gentle upwards slope, you’ll find chef Bowman Brown’s Jackrabbit: a counter-service café informed by the same Scandinavian and Japanese influences that made his fine-dining restaurant Elda (soon to reopen upstairs) one of the best in the state. Those same inspirations work equally well in a more casual environment. Order an open-faced curried egg salad sandwich with trout roe ($12), a dish that could easily merit a menu slot at Copenhagen’s venerable Ida Davidsen restaurant.

If you require a pick-me-up, Time & Tide’s small-batch, house-roasted coffee awaits across the street. Find a better cortado ($3) in Southern Maine … I dare you.


The tourist trifecta of Eventide, Honey Paw and Duckfat continues to draw crowds large enough to make you think it’s 2018 all over again. Unfortunately, throngs of hungry visitors translate into agonizing wait times. But these three Middle Street restaurants, plus their neighbor East Ender, are legendary for good reason.

Eventide’s fried chicken katsu sandwich Ryan David Brown photos

If you decide to brave the mob, lunchtime is your best opportunity to snag a congestion-clearing, Chinese-mustard-slathered fried chicken katsu sandwich from Eventide ($14), or a gochujang-daubed, double-stacked smoked-meat Smokestack Lightning! burger from East Ender ($13).

Just be prepared: Even at lunchtime, you will still have to wait.


The pizza from Bufalina il Leone on Peaks Island. Photo courtesy of Il Leone


Getting out on the water in the summertime isn’t mandatory in Maine, but perhaps it should be. If you’ve been landlocked all weekend, now’s your chance to explore one of Portland’s maritime territories. Hop on a Casco Bay Ferry and explore Peak’s Island by foot or bicycle.

Once you’re worn out, make your way toward Brackett Point, a beachy park on the island’s southwestern tip. There you’ll find newcomer Il Leone, a semi-permanent Neopolitan pizzeria with a mobile oven capable of reaching lava-melting temperatures of 850 degrees Fahrenheit. Snag one of the picnic tables under the trees and order a blistered, naturally leavened Bufalina pie topped with crushed San Marzano tomatoes and gooey buffalo mozzarella ($16.80).

Indoors (or outdoors…your call):

Yes, Virginia, there’s great pizza on Portland’s mainland, too. But finding a spot to eat on a Saturday night in the summer can be as difficult as unearthing buried pirate treasure.

Many of your best options are off-peninsula, including Tipo. This Back Cove sibling of renowned Central Provisions features a roomy, modern dining room and a patio space punctuated by Aperol-colored umbrellas.

Inside or out, menu highlights include an individually portioned pepperoni pizza crackling with heat from Calabrian chili paste ($16), and tender, snail-shaped lumache pasta finished with pecorino, egg yolk, truffle salt, and black pepper ($19), a grownup reimagination of cacio e pepe. If you’re in the mood for a drink, Tipo’s bar is an evergreen highlight, especially cocktails like tangy, bittersweet The Mage, made with pineapple juice, vodka, and Suze ($10).

Espresso and tonic water from Little Woodfords Photo courtesy of Little Woodfords


It’s never too early in the day to seek out one of Portland’s hidden gems, so head to Ohno Café for inventive, world-class breakfast sandwiches. Among my favorites are the #7, a bialy spread with Dijon mustard and filled with egg, cheddar and (wait for it …) Spam. Trust me on this one; it’s the best $6 you’ll spend all weekend. if you’re not quite so adventurous (or a vegetarian), order the #6, a bialy loaded with spinach, tomato, onion, cream cheese and finished with a peppery squirt of Sriracha ($6).

Grab a drink if you’re extra-thirsty (or warding off a hangover). Otherwise, wander up to Uncharted Tea, just off Monument Square, for a Shaken Brown Sugar Coffee ($4) a beverage/snack hybrid featuring nitrogen-bubbled Brazilian cold-brew coffee, oat milk, cinnamon and plump boba pearls.

Bonus: If you find yourself on the opposite end of town, check out the recently relocated Little Woodfords for a bracing and astringent iced espresso and tonic ($4).



During any year other than 2020, the debut of stylish, Art-Nouveau-inspired Via Vecchia would have represented one of the design highlights of the year. A little more than 12 months on, locals and summer visitors are finally waking up to the charms of Josh Miranda’s mostly-Italian, small-plates restaurant. Better late than never.

Via Vecchia’s short rib hash Photo by Anthony Di Biase

The swank interior is certainly gorgeous at night, but the space – including an ivy-draped exterior – is even more impressive during the day, so make a brunch reservation and order the H*R*E*A*M (Hash Rules Everything Around Me), an Eggs Benedict-adjacent dish of short ribs, poached eggs and pistou ($14). If the weekend hasn’t caught up with you yet, and you don’t have a long drive ahead, try one of the restaurant’s large-format cocktails, like the Catalina Wine Mixer, a complex and group-friendly concoction of prosecco, guava and grapefruit juices, and two herbal, bitter amari ($38).


In good weather, stop by the West End Otherside Delicatessen and pick up to-go sandwiches. Otherside’s pork schnitzel Shop Sandwich ($10), a compact parcel of crunchy fried pork cutlet, mustard, caper-and-egg relish, mustard ($10) is one of the finest sandwiches in town. Sandwich in hand, get a bottle or two of Maine Root Ginger Beer ($2.43), then walk a few blocks over to the Western Promenade.

Without expansive water views, the Western Prom has become the Cinderella stepsister to the celebrated and well-trafficked Eastern Prom. But don’t let that dissuade you; it is a verdant delight on a sunny day, with expanses of grass and a dramatic hillside tattooed by switchback pathways and wild sumac trees. On a clear day, you can even see the White Mountains in New Hampshire.

A “FROM AWAY” BONUS: The Drive Back

Heading south before 4 p.m.?

Make a pit stop in Kittery and grab a few airy, sugar-glazed crullers ($3.25) and a lavender latte ($4.95) from Lil’s Café.

Don’t leave the state without an ice cream cone, or two, from Bresca & the Honeybee. Left, artichoke with candied grapefruit and salted pistachios. Right, beach rose with blood orange bitters, poached cherries and candied orange, both held aloft by ice cream scooper Ashley Wilson. Photo by Krista Kern

Heading west before 5 p.m.?

A detour to Sabbathday Lake’s Outlet Beach is in your future. Stop by 2020 James Beard Award finalist Krista Kern’s seasonal Bresca & The Honeybee shack for a few scoops of her ingeniously flavored ice cream ($3.75-$6.75). Daily offerings traverse the spectrum from vanilla to artichoke with candied grapefruit and pistachios, or beach rose with bitters-poached cherries and glacé blood orange.

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