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The 10 Most Popular Restaurants in Portland, Maine, Back in 1996

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The 10 Most Popular Restaurants in Portland, Maine, Back in 1996


It seems commonplace now that people visit Portland, Maine, for the food.

Portland is home to a mix of classic and new restaurants that people travel long distances to experience.

But that wasn’t always the case. Looking back 30 years ago, Portland, Maine, was home to delicious restaurants that were not home to many frills or fanfare.

Some of those restaurants are still rolling along today, others failed to move forward.

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Here’s a look at the 10 most popular restaurants in Portland, Maine back in 1996.

Back Bay Grill

Officially opening its doors in 1988, the Back Bay Grill quickly became one of the places for fine dining in Portland, Maine.

In 1996, it was one of only a handful of restaurants within the city that would be considered upscale.

The Back Bay Grill ended its lengthy run when it closed permanently in 2022.

Becky’s Diner

Opening in Portland’s waterfront in 1991, it didn’t take long before Becky’s Diner was a regular part of the working waterfront’s routine.

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As the working waterfront began diminishing, Becky’s has managed to transform itself into a place locals still enjoy while simultaneously serving as a tourist destination.

35 years later and Becky’s is still going strong.

Granny’s Burritos

Opening in 1995, Granny’s Burritos has taken on an almost mythical presence for that fondly remember it.

Granny’s called several different spots around time home over the years but remains fondly remembered for its stellar nachos and signature burritos.

The last iteration of Granny’s Burritos officially closed in 2017.

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Fore Street

Officially opening in 1996, Fore Street is widely considered the restaurant that took Portland, Maine, and put it on the map for food.

Almost from the day it opened, Fore Street became a cornerstone to fine dining in the city and laid the groundwork for many other upscale restaurants to follow.

Fore Street still remains one of the most popular restaurants in Portland, Maine, 30 years after it initially opened.

Squire Morgan’s

Now home to Cutie’s, the corner of Market and Milk streets was once home to one of Portland’s most popular pubs called Squire Morgan’s.

Squire Morgan’s had a fantastic run in the city through the 80’s and early-90’s before a fire burned the restaurant in 1996.

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Squire Morgan’s rebuilt but it was never the same and closed permanently in 1998.

DiMillo’s Floating Restaurant

There is something unique and elegant about dining aboard a floating restaurant. That has been the draw for DiMillo’s since it opened in 1982.

Like Back Bay Grill, DiMillo’s was one of a handful of restaurants in Portland during the mid-90’s where people could visit and receive upscale service and dining.

Despite the restaurant scene changing drastically around it, DiMillo’s remains a destination restaurant for many visiting Portland.

Silly’s

Even amongst a slew of restaurants serving pub grub and classic New England fare, Silly’s always stood out.

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It was a quirky spot with a eclectic menu that people consistently flocked to, especially on the weekends. It became a staple in the city throughout the 90’s.

Silly’s had a couple of starts and stops in Portland in more recent times before finally reestablishing itself in Standish.

The Sportsman’s Grill

Opened in 1952, the Sportsman’s Grill on Congress Street was a staple of dining in Portland, Maine, for decades.

The restaurant was sports themed as the name would suggest and evolved over the years to draw in sports fan and casual diners.

1996 proved to be one of the final years for the Sportsman’s Grill as it closed permanently in 1997.

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The Great Lost Bear

Originally known as Grizzly Bear, the Great Lost Bear got a name change in 1981 and really grasped a rapid fanbase throughout the 80’s.

The Great Lost Bear has always been known for its large menu and larger portions and was one of the first spots in town to fully embrace craft beer and champion it.

The Great Lost Bear remains a favorite for many as it approaches its 50-year anniversary.

Walter’s

Originally opening its doors in 1990, some credit Walter’s as a stepping stone restaurant to what most see throughout Portland today.

It was a cornerstone upscale restaurant throughout the 90’s and eventually sold in 2004.

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Walter’s moved from its original location at 15 Exchange Street to 2 Portland Square in 2009 and operated there for years before closing permanently in 2019.

The New York Time’s Best Restaurant Lists Feature These 7 Maine Spots

Gallery Credit: Sean McKenna

61 Maine Restaurants That Closed in 2025

Gallery Credit: Sean McKenna





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Maine

A Weekend in Maine | Cup of Jo

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A Weekend in Maine | Cup of Jo


A Weekend in Maine

“Do you ever think we could find some woods to walk in?” my outdoorsy 12-year-old asks me, every now and again. As a kid growing up in New York City, Anton appreciates all the skate parks and bagel shops, but he also really craves nature, like in his bones.

Joanna goddard anton maine

So, when school got out, I offered to take him for a weekend in Maine, a place with not only woods but also lakes and rocks and periwinkles that come out of their shells when you hum. We were both really excited.

aragosta hotel maine

The first night, we were lucky enough to snag a room at Aragosta, a beautiful small hotel in Deer Isle that Alison had recommended.

aragosta hotel breakfast maine

The chef-owner, Devin Finigan, is famous for her seasonal tasting menus, but we focused on the breakfast that came with the room, including these Maine blueberry pancakes. I don’t even usually like pancakes and these blew my mind.

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Joanna goddard chess

We also played a LOT of chess on our little travel board.

A Weekend in Maine

After breakfast, we set out to hike up Blue Hill Mountain.

A Weekend in Maine

Here’s the summit!

stonington maine

In the afternoon, we explored the charming fishing village of Stonington…

Julie O'Rourke Maine

…then joined my friend Julie (of Rudy Jude fame) and her family for dinner at the Burnt Cove Boil.

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burnt cove boil

Basically, a crab gets plonked down in front of you, followed by a corn on the cob, then a lobster, then a classic ice-cream sandwich. Julie and her husband Anthony taught us how to get all the meat out. (Their kids were already pros.)

burnt cove boil

Afterward, the four boys scrambled around on the rocks, while the adults chatted. It’s always such a treat to hang out with people who live in the place you’re visiting, don’t you think? Julie and Anthony described how they brought their recently hatched chicks into their home to keep them warm, and all the peeping was sooooo loud — and then a cricket got into the house and added to the noise and no one could find it and everyone was going nuts, haha. Very different from city life!

asticou hotel

The next day, Anton and I stayed at the lovely Asticou Hotel near Acadia National Park.

Jordan pond hike Acadia national park

We drove to a couple trailheads but they were PACKED — you had to stand in a long line, just to start the hike! Luckily, we found a quieter area and took a long walk around Jordan Pond, playing Would You Rather and Categories along the way. Do you have any favorite travel games?

anton stones

anton maine

Finally, we skimmed stones on our last afternoon before heading back to Brooklyn.

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A Weekend in Maine anton

Epic travel buddy

Oh, Maine, what a magical place! Not pictured, of course: traffic, grumpy preteen moments, locking our keys in the rental car, etc., but all that’s to be expected.

Have you been to Maine? Do you live there? What parts do you love? Any pro tips? I’d love to hear. xoxo

P.S. Our Maine trip — and another amazing hotel — when the boys were much younger, and a Maine home with a bedroom looking over water.





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Matt Dunlap wins primary in Maine’s 2nd District as Democrats seek to hang on to Jared Golden’s seat

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Matt Dunlap wins primary in Maine’s 2nd District as Democrats seek to hang on to Jared Golden’s seat



Matt Dunlap won the Democratic primary in Maine’s 2nd Congressional District after three rounds of ranked-choice voting, the state’s Secretary of State’s office announced Friday. 

Democrats are seeking to hang onto a seat in a district that President Trump won in the last three presidential elections. State Sen. Joe Baldacci led after the first two rounds of ranked–choice voting, but Dunlap overtook him after challengers Paige Loud and Jordan Wood were eliminated. 

Democratic Rep. Jared Golden, a moderate, is retiring after four terms. His decision not to run for reelection was a blow to Democrats’ efforts to retake the House majority. 

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In the 2024 election, Golden was one of 13 Democrats to win a House race in a district also won by Mr. Trump. Golden declined to endorse Kamala Harris in the 2024 election and has voted with Republicans on several issues, including measures to avert a shutdown and on reining in Mr. Trump’s war powers authority. 

Dunlap, the state’s auditor, will face Republican Paul LePage in November’s general election. LePage is a former two-term governor who ran unopposed in the GOP primary. As of May 20, LePage had $1.2 million cash on hand while Dunlap had less than $100,000, according to Federal Election Commission data.

Dunlap’s win marks a defeat for House Democrats’ campaign arm. The Democratic Congressional Campaign Committee endorsed Joe Baldacci, a state senator, saying he “has never lost an election and has consistently overperformed Democrats up and down the ballot, including a 3-point overperformance of the presidential ticket in 2024.” 

Baldacci was the runner–up, the Maine Secretary of State’s office said. The results were announced 10 days after voters went to the polls due to the ranked-choice tabulations. 



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4-year-old girl in critical condition after near drowning at Kennebunk hotel pool

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4-year-old girl in critical condition after near drowning at Kennebunk hotel pool


KENNEBUNK, Maine (WGME) — A 4-year-old girl is recovering after firefighters say she nearly drowned in a hotel pool in Kennebunk.

It happened at the Hampton Inn Saturday at around 9:30 p.m.

Kennebunk Fire Rescue says it got a call for someone not breathing.

When first responders got there, they say they found a 4-year-old in cardiac arrest after almost drowning.

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That girl was flown to a Portland hospital, and she remains in critical condition.

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The cause of the incident is unclear at this time.



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