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DiMillo's On the Water: An Anchor on the Portland, Maine Dining Scene

 Fresh seafood, lobster dinners and unforgettable water views provide a memorable experience at this one-of-a-kind, iconic family-owned and operated restaurant

Dimillo's On the Water restaurant in Portland, Maine.DiMillo's On the Water.

Article and photos, unless otherwise noted, by Eric Hurwitz. Article created on 2/24/2020.

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If one took all the special things about a coastal New England dining out experience and put it all in one place, DiMillo's On the Water in Portland, Maine would serve as the gold standard prototype.

Stunning water views from the converted car ferry's first and second deck lend some of the most impressive restaurant scenery in New England. Boats bobbing up and down in the harbor water act as if they were nodding approval at the restaurant.
The summer ocean breeze and salt sea air from the outdoor dining decks serve as Mother Nature's flavor enhancers to further set the memorable, refreshing classic coastal Maine tone. "You don't get much more of a waterfront front view than actually being on the water," said Chuck Igo, morning personality at Rewind 100.9 FM in Portland, of DiMillo's perfect location.

Right on the water at DiMillo's in Portland, Maine.
Dining by the water at DiMillo's.

Located at the Portland waterfront's Long Wharf, this unforgettable floating restaurant possesses an uncanny ability to take the customer away from daily life and into another place -- much like the feeling of feeling fully connected to a favorite vacation spot.

Many travel many hours to enjoy the water views and local seafood bliss. Mary Ellen Mercier, who lives about two-and-a-half-hours away in a small town southwest of Boston, Mass. has made DiMillo's an annual tradition with her husband, Ed.

"My husband and I celebrate our anniversary at DiMillo's every July," said Mercier. "The food is exceptional, worth the wait. Beautiful sunset on the bow while watching boats coming and going. A real romantic experience."

Dining at the bow at DiMillo's in Portland, Maine.
Enjoying deck dining at DiMillo's. Photo credit: Johnny DiMillo.

Of course, a coastal Maine waterfront restaurant without local seafood would sink the dining experience to "below C level" (sorry, bad pun).  Think of DiMillo's as a big, high volume restaurant with the passion of a small restaurant, courtesy of a tight multi-generational family-run business and a highly skilled Maine-born executive chef (more on that shortly).

DiMillo's specializes in fresh-off-the-boat, locally caught seafood that is forever associated with the Maine way of life starting, of course, with single or double steamed lobster all caught within a mile of the restaurant. Maine lobster from DiMillo's On the Water in Portland, Maine.
Steamed lobster with mussels. Photo credit: Johnny DiMillo.

DiMillo's On the Water, however, shells out much more than steamed Maine lobster. As an extension of that regional favorite dish, lobster here comes in the form of baked stuffed, club sandwich, a "lazy lobster" sauteed in butter, mac and cheese, a deep fried lobster tail or an overflowing lobster roll with tender flavorful lobster and very little filling...

Lobster roll from DiMillo's On the Water in Portland, Maine
Lobster roll.

The lobster stew reigns as a culinary marvel with chunks of lobster in a creamy, flavorful fish broth. What a difference from the overly-thick-flour-base-meets-frozen-lobster-meat versions served in many restaurants!

Loads of fresh Maine lobster in this lobster stew from Dimillo's On the Water in Portland, Maine.
Lobster stew.

A look at the family-friendly lunch and dinner menus showcases a well-balanced variety, of course, steered by local seafood like native haddock, Atlantic salmon, fried clams and scallops. DiMillo's On the Water is not all about seafood, however, as they also focus on having something for everyone including Certified Angus Beef® sirloin, filet mignon and prime rib (Friday and Saturday until it runs out!) dishes, Tuscan fried chicken, gourmet salads, homemade soups and chowders, and traditional Italian dishes (many featuring seafood).

Filet mignon from DiMillo's On the Water in Portland, Maine.
Filet mignon. Photo credit: DiMillo's Facebook page.

Sandwiches are substantial and mouthwatering, including this calamari burger that wonderfully combines tastes from land and sea...

Calamari burger from DiMillo's in Portland, Maine.
Calamari burger. Photo credit: DiMillo's Facebook page.

The appetizers are most appetizing like the jumbo shrimp, steamed Maine clams, sauteed mussels, crispy fried oysters, bacon wrapped scallops, Sicilian meatball, spicy seared tuna and Polenta fried calamari.


Desserts can take on a wonderful Maine theme like this wild Maine blueberry cobbler with vanilla ice cream...

Maine blueberry cobbler from DiMillo's On the Water in Portland, Maine.
Maine blueberry cobbler with vanilla ice cream.

Such a nice place to eat but also with an atmosphere that matches the high quality of the food!  Once passing through the gangplank...

Entrance to DiMillo's On the Water in Portland, Maine.
Entering DiMillo's.

and the perimeter of the restaurant...

Walking toward the main dining area at DiMillo's On the Water in Portland, Maine.
Walking the corridor at DiMillo's.

the dining areas achieve a beauty that is rarely seen at large, high volume restaurants. The aura consistently remains unaffected, unpretentious and genuine throughout the whole space. It also happens to be ultra-comfortable and cozy whether at the main dining room...

Dining room at DiMillo's On the Water in Portland, Maine.
Main dining room.

or a more intimate setting by a fireplace...

Dining area by the fireplace at DiMillo's On the Water in Portland, Maine.
Cozy setting at DiMillo's.

The bar area also feels so right (and offering many fine local wines, beers and cocktails)...

The bar at DiMillo's in Portland, Maine.
Bar area.

and also affords splendid water views...

View from the bar at DiMillo's On the Water in Portland, Maine.
Water view from the bar.

Some parts of the restaurant show the Portland skyline, which comes across through the windows as almost like a painting. It's a sight you could look at all day.

View of Portland, Maine skyline from DiMillo's On the Water.
Enjoying the Portland skyline.

It is clear as a sunny day at the harbor that DiMillo's On the Water is not only in the business of serving Maine seafood with water views but also creating unforgettable memories. Whether a day with the family, date night out, a wedding, banquet, business meeting, special event, anniversary or rehearsal dinner, it's hard to think of a better place to be.

"Been going there for 40 years and I've never been disappointed," said Igo. "We've been for dinners for two and dinners for 14, as well as company/work functions, weddings and other events, too. The DiMillo family has always worked hard to put out the best experience and food. Personal favorite: The 'Chowdah!' I'm a 'thick chowdah' guy and I could always pick theirs out when serving as a judge at the annual Chili & Chowder Challenge fundraising event here in Portland. And, yeah, the scenery is pretty cool."

DiMillo's On the Water: Born out of a close-knit, hard-working Portland family

The DiMillo family at DiMillo's On the Water in Portland, Maine
The DiMillo family. Photo credit: DiMillo's.

Tony DiMillo, who immigrated to the United States from Canada, first opened a restaurant in 1954 as Anthony's on Fore St. in Portland. The restaurant became famous for the slogan, “The clams you eat here today slept last night in Casco Bay."

When development began to change the look of Fore St., Tony moved his business in 1960 to Center St.  In 1965, Tony opened DiMillo’s On the Waterfront just across the street from the current DiMillo's location.

As an astute businessman aware of the city's emerging waterfront presence, Tony purchased then-blighted Long Wharf, quickly filling all 120 slips.

Tony DiMillo, founder of Dimillo's restauarant in Portland, Maine.
Tony DiMillo. Photo source: DiMillo's web site.

1982 then brought the most significant transitional business moment in DiMillo's history: Tony and family converted a car ferry into DiMillo's Floating Restaurant at Long Wharf. It became the only floating restaurant on the East Coast.
To this very day, the restaurant provides a larger-than-life sight. The car ferry's overall length is 206 ft. with a beam of 65 feet and weighs 701 tons. The ferry seats more than 600 guests in the first deck dining room, Port Side Lounge, second deck dining rooms and three outside decks.

Tony died in 1999 but the legacy continued with five of his nine children working on the property which, in addition to DiMillo's On the Water, includes DiMillo's Marina and DiMillo's Yacht Sales.

Walking around DiMillo's On the Water, there almost seems to be as many DiMillos as fish in the sea. Tony's sons help carry on the tradition. Steven serves as the manager. He started in the family business at eight-years old, beginning as a dish washer and working in every department prior to his current role as manager. Steven also serves on the board of the Maine Restaurant Association.

Johnny, a U.S. Army veteran, has been at DiMillo's since high school and works as manager and social media manager.  Steve's son, Steve, Jr. -- a University of Vermont graduate with a bachelors degree in economics -- heads the banquet department. Steve Sr.'s daughter, Chelsea, works as the beverage director. She is a University of Southern Maine graduate with a degree in studio art. Brother-in-law Tony Quattrucci is the kitchen manager. Nieces work in various parts of the restaurant.

"I love working with family," said Chelsea. "I am one of the few of my generation who remembers grandpa and all he did. To continue his legacy is fulfilling. My dad, he's sometimes gives me the hardest time but it is only for the better. It's all about the work ethic and enjoying what we do. My dad has instilled that into us. Since a very young age, there hasn't been six months gone by that I haven't worked here."

Niece Lena DiMillo has only worked at DiMillo's for a few months but enjoys her full-time position at the front of the restaurant.

"It's nice and comfortable and I like helping out family and the customers," said Lena. "I would like to work here for the rest of my life."

"Familiar faces" outside the family have also worked at DiMillo's for many years including kitchen manager Fred Breton who began employment here in 1988. Lisa Baugher, the bar manager, has worked at DiMillo's for several years. Missy Anderson, the dining room manager, started at DiMillo's in 2009 first working as a waitress. 

Melissa Bouchard has been employed at the waterfront restaurant since 2001. She has served as executive chef for nearly the past decade and helped transformed DiMillo's food from good to great.

The Eastport, Maine native once had aspirations to be a nurse but found better career wellness by pursuing her love of cooking. The move proved to be correct as Bouchard
earned 2009 and 2012 finalist accolades for the Maine Lobster Chef of the Year competition. She also serves as a Chef Ambassador for the Maine Lobster Promotion Council. Additionally, Melissa was appointed in 2012 to represent the State of Maine in the Great American Seafood Cook off in New Orleans, La. Melissa was also named the Maine Restaurant Association’s first female Chef of the Year in 2013.

Melissa Bouchard, head chef at DiMillo's in Portland, Maine, holds a cooking classic at this legendary local restaurant.
Melissa holds a cooking class. Photo credit: Johnny DiMillo.

"She has really helped elevate the food," said Steven, of Bouchard. "We had good recipes but just weren't using them enough. We always brought in fresh fish locally but needed to do more with that seafood. Melissa brought a creativity that really changed things over the past several years. We once struggled, trying to keep up with the volume of customers coming in. In a small community, it takes a while to shed the tourist trap restaurant image but we did just that."


As further expression to DiMillo's refreshed commitment to top-notch food, Melissa holds cooking classes with the public at the restaurant. It has become a very popular event.
Cooking classes include an appetizer and entree, both served with a glass of paired wine.

Steak dish at DiMillo's in Portland, Maine.
Steak dish created during cooking class at DiMillo's. Photo credit: Johnny DiMillo.


Even during the off season, DiMillo's brings in a robust business with more of a local crowd. Aptly named "Locals’ Season," DiMillo’s On the Water shows appreciation to the Portland and vicinity crowd with an updated menu including happy hour and early dinner specials.


"This is our favorite time of the year because we can enjoy spending more time with locals and their families," said Chelsea.

"Ferry" Tales Do Come True

The converted car ferry has a rather fascinating history that eventually led to the birth of a landmark Portland restaurant. Here is its chronology (source: DiMillo's web site)...
 
1941
Commissioned “The New York,” it ran as a car ferry between New Castle, Delaware and Pennsville, N.J.

 "The New York" car ferry from 1941 is now DiMillo's Restaurant in Portland, Maine.
"The New York." Photo source: DiMillo's web site.

1951 Sold to the state of Virginia and renamed “The Norfolk.” Ran between Norfolk and Hampton, Va.

1958 Sold to the state of Rhode Island and renamed “The Newport.” Ran between Newport and Jamestown, R.I.

1969 Sold to the city of Pawtucket, R.I. and used as housing for a youth center art colony.

1977 Sold to the Setaucket Yacht Club of Port Jefferson, N.Y. and utilized for boat storage and as its clubhouse.

1980 Purchased by the DiMillo family.

Car ferry arrives in 1980 to Long Wharf in Portland, Maine -- soon to be converted into DiMillo's Restaurant.
The arrival of the car ferry to Portland. Photo source: DiMillo's web site.

1982 Opened as DiMillo’s Floating Restaurant.

1994 Installed a new hull at the Bath Iron Works dry dock.

A new hull installed on "The New York" car ferry that became DiMillo's Floating restaurant in Portland, Maine.
A new hull installed. Photo source: DiMillo's web site.

Situated at the end of Long Wharf Promenade, the location today offers access to the waterfront as well as being a "gateway" to the restaurant, DiMillo's Yacht Sales and DiMillo's Old Port Marina. What Tony created is stuff made out of the American Dream. He grew up poor in Portland but found a way to bring tourism and restaurant customers to the waterfront in place of a once inaccessible industrial waterfront.

The DiMillos family were mostly masons -- how poetic it must have been to see builders of stone evolve into builders of small business successes.

Conclusion

Inviting dining area at DiMillo's On the Water in Portland, Maine.
Welcoming dining area at DiMillo's On the Water.

One of the biggest challenges for tourists and locals to find in a restaurant is a combination of essentials: consistency, quality, top-notch service, good value for the money and a memorable atmosphere.

DiMillo's On the Water attains all of these critical tenets starting with its foundation of a long-established family-owned and operated business that commits to fresh local seafood, the presence of a creative chef and a most pleasing, memorable dining setting by the water. It's like the restaurant version of an all-inclusive resort -- that is, offering something special for everyone. Plus, it feels like Maine here. What could be better, for example, than dining out on a waterfront deck over a few drinks with outstanding seafood that has been sourced locally?

A waterfront dining out experience at DiMillo's in Portland, Maine.
Dining by the water at DiMillo's. Photo credit: Johnny DiMillo.

Many Portland restaurants have come and gone through the years with a good number of the traditional spots, unfortunately, falling into the latter category. Thankfully, DiMillo's On the Water survived those years including the bad economies and "hot" restaurant trends. Like fine wine, DiMillo's just kept getting better and better instead of just resting on its laurels.

As Portland continuously transforms into one of New England's most beloved cities, the dining out scene has evolved accordingly, also. Coffeehouses, cafes, brewing companies, bistros and bakeries have saturated the revitalized 18th century brick neighborhoods in and beyond the prized
Old Port District
, just up the street from DiMillo's.

Many locals and visitors, however, stay with the traditional ways of DiMillo's On the Water, knowing that the power of Maine Lobster, unforgettable coastal scenery and a menu to satisfy all appetites creates an irresistible place to eat. While the DiMillos have come a long way since Tony first opened a restaurant in 1954, family members have carried on the grand tradition -- just on a larger scale.

"There's something to be said about fresh fish brought to us daily by long-time vendors," said  Steven. "We are now better than ever by paying attention to our brand, serving delicious local seafood and more, having a welcoming atmosphere and keeping the staff happy!"

DiMillo's On the Water is located at 25 Long Wharf, Portland, ME. Tel. (207) 772-2216.
Web site:
https://www.dimillos.com/

Facebook page:
https://www.facebook.com/portlandmainelobster/

Instagram page: https://www.instagram.com/dimillos/
YouTube Page: https://www.youtube.com/channel/UClY4fVK9D4ya7W4TZ8cmG2g

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Next stop in New England: Dining in a converted car ferry at DiMillo's On the Water at the waterfront in Portland, Maine.


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If you love dining out by the sea in Massachusetts and Rhode Island, be sure to check out...
Coast Guard House, Narragansett, R.I.

The Top of the Newburyport Lighthouse, Newburyport, Mass.
CabbyShack, Plymouth, Mass


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