The Main Street Diner doesn’t look like other diners. For one thing, the Portland eatery is located inside a 200-year-old clapboard house, which it shares with two upstairs apartments and, next-door, Zah’s Bait and Tackle. For another, the seafoam stucco walls of the one-room restaurant are covered with colorful children’s art—pictures of the world in primary colors— providing a vibrant background for the restaurant that points toward its equally vivacious character.
“Owning a diner is like being married twice,” the owner told me over brunch last Wednesday. “I figured that I was unable to see my daughters much, but I could [still] have these reminders…One of my employees is a retired teacher in the Portland schools system. Every child in the third, fourth, fifth, and sixth grade makes it up on the wall—we change it every month.”
The diner has deep roots in the community. One regular who moved to Portland in the 1950s estimated that it was established around 1960 in the same house in which it now operates. Since then, the restaurant has changed hands several times, with this most recent owner arriving seven years ago.
“I was born and raised in Fort Lauderdale,” she told me. “After my father passed away, I needed to get out of Florida, and I had always vacationed in Connecticut. I was an Elementary Ed. Major, but I ended up here. Life changes.”
When she bought the diner, she added cinnamon raisin French toast to the menu, but not much else.
“There wasn’t much to change,” she said. “Breakfast is breakfast.”
And a delicious breakfast it is. The diner’s menu is limited in comparison to some of its peers in the area, but all of the food that my party tried was great. The French toast, which comes in plain, banana, blueberry, and the aforementioned cinnamon raisin varieties, was pronounced “really good;” the specialty Portlander sandwich (egg, bacon, cheese, and tomato on a hard roll or English muffin) was delicious; the western sandwich was nicely cooked; and the home fries were uniquely and delectably spiced. A lunch menu includes chilidogs, buffalo chicken wraps, and more. The diner also hosts set-menu dinners every Tuesday night.
A smaller menu means flexibility, and the diner’s rotating selection of specials relies heavily on the preference of regular customers.
“One man said, ’Are you ever going to have franks and beans as a special?’ And I said, ’Well, I have franks and I have beans. I guess I’ll do it,’” the owner told me. “Certain people like sloppy joes, so you’ll have ’Bill’s favorite’ or the like. That’s the best part of the job—I have a rapport with the customers. You see them walking up the sidewalk, and you know what they’ll get because it hasn’t changed for three years or longer.”
The diner sees a lot of locals—what the owner called “Town Hallers” (selectmen), business people, and the occasional Wesleyan professor. The clientele is diverse in age, from parents with young children to retirees who’ve been coming for years, some for decades.
“I’ve made a lot of close friends, but I’ve also attended a lot of funerals,” the owner said.
What makes the Main Street Diner unique, besides its common-ground sensibility and colorful decorations, is this sense of togetherness—not just as a place to meet, but as a social niche in itself.
“Portland is a small town where everybody knows everybody,” the owner remarked in a moment of reflection. “You could sneeze right here and they’d know about it over there…But they accept me. This was my way of fitting in. This is a hard town if you’re an outsider, but once they get to know you, they’re very lovely and accepting.”
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The Lowdown:
Located at 246 Main Street, Portland (Just over the bridge).
Five minutes across the Connecticut River on CT-17.
Phone for directions: (860)342-3826.
Open Monday-Friday 5 a.m.-1:30 p.m., Saturday 5 a.m.-12 p.m., Sunday 7 a.m.-12:30 p.m.
Please note that the diner does not take credit or debit cards.
Essential menu items:
2 eggs, 2 slices of French toast/2 pancakes, meat—$5.75
Cheese omelet—$4.75
French toast—banana or blueberry—$3.50
3 chocolate chip pancakes—$4.50
“Portlander” (also available without meat)—$2.95
Buffalo chicken wrap—$5.50
Chilidog—$3.25
Also try in the area:
Brownstone Park—161 Brownstone Avenue, Portland. A quarry water park with floats, cliff diving, a zip line, and more in the summer. A park with 40 acres of hiking year round.
Portland Historical Society—492 Main Street, Portland. Learn a little something about Portland and Middletown, the way they use to be.
Extravaganza Music Theater Company—8 Myrtle Road, Portland. Because there aren’t enough show tunes in your life.
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