5 min read

Astute observers of Portland’s celebrated restaurant scene won’t be surprised to see that two of restaurateur Dana Street’s three restaurants have made our short list of spots best suited for special occasions: Fore Street and Scales. (Street himself has been nominated this year for a James Beard award for Outstanding Restaurateur.)

The other two top spots, as named by the Mainers and food experts who answered our call for input, go to Leeward and Isa Bistro. These four, all in Portland and all terrific, were the top vote-getters, but many other wonderful places in the city and beyond were nominated, too. When it comes to special occasions, or really any occasions, we have an embarrassment of restaurant riches.

Here are the readers’ and experts’ favorites:

JUMP TO MORE ON EACH PICK



Fore Street

Diners fill Fore Street on a busy Monday evening. (Daryn Slover/Staff Photographer) Purchase this image

288 Fore St., Portland. 4:30 p.m.-close daily. 207-775-2717. forestreet.biz. Appetizers, $14-$25, entrees, $26-$52. Reservations by phone or Open Table.

“Can’t beat the classic,” restaurateur and chef Chad Conley (Rose Foods, Palace Diner) said in nominating the pioneering Fore Street restaurant, which has delighted Mainers and tourists with its rustic, ultra-local, ultra-seasonal food since 1996. To no small extent, Fore Street, under founding chef Sam Hayward, put Portland’s food scene on the national map when he took home Maine’s first James Beard award for Best Chef: Northeast. But the remarkable thing is less that Fore Street led the way, and has served as training ground for so many talented Maine chefs, but that it has maintained its place among the state’s best and most beloved restaurants for more than three decades. 

The service is stellar. The room — a seemingly unlikely combination of old factory, thrilling theater and refined handcraft — is gorgeous. And the wood-fired, farm-to-table food remains as consistently excellent as back in the day; sourdough breads from Maine-grown grains and baked by its sister business Standard Baking Co. add to diners’ pleasure. As one respondent put it, “Fore Street is a total standout — warm, lively and special the moment you walk in.” Food writer Kathy Gunst summed it up simply: “It just never disappoints.”

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ISA BISTRO

Tagliatelle bolognese at Isa Bistro in Portland. (Daryn Slover/Staff Photographer)

79 Portland St., Portland. 4-9 p.m. Sunday-Monday and Wednesday-Thursday; 11:30 a.m.-9 p.m. Friday-Saturday; closed Tuesday. 207-808-8533. isaportlandme.com. Appetizers $10-$22, entrees $25-$49. Reservations on Open Table.

If you’re the sort of person who thinks big, grand, lavish gesture when it comes to special occasions, the intimate, off-the-beaten-path Isa Bistro may strike you as a dark horse candidate. But if charming, welcoming, relaxed and (it goes without saying) delicious are more your style, Isa Bistro is your spot. 

The intimate neighborhood restaurant, opened in 2015 by Isaul (chef and 2023 James Beard semifinalist) and Susie Perez (wine director), serves what some might call a “carefully curated menu.” But that phrase feels pretentious for this sweet, very personal spot. Menu items like Lobster Tostada with Cabbage, Avocado Aioli and Browned Butter, or Seared Branzino with French Lentils, Spinach and Fried Shallots make it clear the dishes “are influenced by the places we’ve been and the things we love,” as the couple puts it on their website. 

One reader said he tells all his out-of-town friends, “If you have time for only one place to go in Portland, make it Isa.”


Leeward

Diners sit at the bar at Leeward in 2022. (Brianna Soukup/Staff Photographer) Purchase this image

85 Free St., Portland. 5-9 p.m. Tuesday-Saturday. 207-808-8623. leewardmaine.com. Appetizers $15-$28, entrees $28-$52. Reservations on Resy.

The food at this Arts District favorite is interesting, balanced and beautiful. With a menu focused on ostensibly simple dishes like Mafaldine with Spicy Calabrian Pork Ragù, Tomato, Oregano and Pecorino Romano, or Bucatini with Pomodoro, Basil, Confit Garlic, Parmigiano-Reggiano and Burrata, there’s scant margin for error. No worries on that account from the expert kitchen.

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Leeward’s muted palette and gentle lighting seem to have escaped from an Arizona spa. The service is friendly and attentive, but never overbearing. Add in the approachable yet “creative” seasonally focused food, and Leeward is a shoo-in for any list of great restaurants in Maine. Both the restaurant itself, opened in 2020, and its chefs have been nominated for multiple James Beard awards, including one for chef-owner Jake Stevens just this year. Said Room for Improvement bar owner Arvid Brown, “The food, the wine and the staff are all some of the best in the city.”


SCALES

Waitstaff line up to take orders to diners in front of the huge lobster tank at Scales. (Derek Davis/Staff Photographer)

Maine Wharf, 68 Commercial St., Portland. Winter hours: 5-9 p.m. Sunday-Thursday; 4:30-9:30 p.m. Friday-Saturday. 207-805-0444. scalesrestaurant.com. Appetizers $13-$22, entrees $28-$65. Reservations on Open Table

Pair loud, high-energy fun with expertly crafted versions of New England seafood classics like lobster bisque, fried clams and lobster rolls, and you’ve got Scales. The menu also spotlights such traditional regional and sea shack sides and desserts as anadama bread, coleslaw and Indian pudding, as well as elegant nods to executive chef Frederic Eliot’s French background: Think Smoked Fish Pate with Olive and Caper Relish, or Baked Haddock with Black Trumpet Mushrooms, Leeks, Hakurei Turnips and Fumet Cream. 

The setting and menu at Scales are in deep conversation with Maine’s culinary past and present. Small wonder the place is always packed. Go for the striking space and the spectacular view of the setting sun from Maine Wharf on Portland’s waterfront; stay for what one reader described as “the consistently great food.” Said another, “I cannot think of a better place in Portland to celebrate.”

Explore more of our Best 32 restaurants

Tell us about your favorite spots to celebrate a special occasion in the comments below or weigh in with other commenters on our entire Best 32 picks here: What are your favorite restaurants? Which did we miss?

Peggy Grodinsky has been the food editor at the Portland Press Herald since 2014. Previously, she was executive editor of Cook’s Country, a now-defunct national magazine that was published by America’s...

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