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.

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.

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.

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.

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.

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.

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.

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.