Coastal Dining on the Water: Harborside or Ocean View

Waterfront Dining in the Old Port

Portland is a peninsula surrounded by water: Fore River to the south flows into the harbor, the Atlantic Ocean sits on the eastern edge of the city and in turn fills the northern Back Cove tidal basin. This framework of tributaries makes it a perfect city for waterfront dining.

The Old Port Exchange, "The Old Port" as locals call it, is the historic part of downtown Portland and offers the largest selection of dining options at the water’s edge, and offers inexpensive options to dine while immersed in sea views.


Becky’s Diner, at the base of High Street on Hobson’s Wharf is a Portland institution, and a great way to start, continue or end your day. The family-run diner opens for fishing industry workers and other early-risers at 4 a.m. A line will form out the door after the sun comes up and continue until well after noon, but Becky has trained her daughters to turn tables well and the line moves quickly. Plus, customers who enjoy the vintage counter service can pass the line and go right in, if there’s a stool. Breakfast is served until the last dinner entrée is ordered at 9 p.m. The popular Commercial Street diner added a second story in recent years so you can dine on the deck while seagulls swoop over nearby lobster boats.


Down Commercial Street, between Chandler's and Long Wharves, Portland Lobster Company’s neon lights attract the hungry and thirsty alike. The Company’s kitchen is little more than a shack perched above the tidal harbor waters. It has limited indoor seating with views of the boats slipping in and out of port, as well as a narrow outside deck to wait or have a beverage on, but along the back to Chandlers Wharf is the true dining area – an expansive deck, partially tented to escape unusually hot sun or unexpected rain, with a full outdoor bar and live music nightly. The offering is traditional Maine fare: lobster rolls, lobster bisque, and of course, lobster, all fresh off the boat. Lucky Catch Cruises offers a two-hour trip into Casco Bay to see, or even experience, how to catch lobsters. The crustaceans trapped at the end of that voyage can be purchased at cost and brought directly to the Portland Lobster Company which will prepare and serve them up for your next meal.


At the end of Long Wharf, beyond a historical piece of the Berlin Wall, floats a massive white vessel with huge windows and blue accents emblazoned with the name DiMillo’s. Tony DiMillo was a Portland visionary who had a retired car ferry retrofitted to create a unique waterfront dining experience. When DiMillo's On the Water opened in 1982, it was one of the only gems in an otherwise neglected and dilapidated area. Today, under the management of his children, DiMillo’s remains one of the premier jewels of the vibrant seaport. Chef Melissa Bouchard’s American cuisine complements the dramatic harbor vistas seen from the ship’s rooftop decks or its spacious dining areas occupying the ferry’s former passenger areas and car bays. A port-side deck off the lounge is a relaxing way to enjoy a meal as yachts rock in the marina below.


Down the street at Portland Pier, a line of lobster boats unload their catch on Custom House Wharf. The Wharf surprises with many shops (Sea Bags, Harbor Fish Market), clubs, and waterfront restaurants. The Porthole is another long-time haunt for local fishermen, but its wonderful menu and affiliation with the adjacent Comedy Connection has turned these dockside venues into weekend hot spots and happy hour mainstays as well.

A stone’s throw away, fishermen, locals, and visitors pack the restaurant as well as the three-storied deck at the Dry Dock Restaurant & Tavern on Commercial Street. The local favorite was made famous by Linda Greenlaw’s (of "The Perfect Storm” fame) book, "All Fishermen Are Liars: True Tales from the Dry Dock Bar”. The atmosphere lost a little grittiness as bibliophiles contributed to its gentrification, but the architecture, food, and wonderful harbor side sightlines make it more popular than ever.

Just a few doors down on Maine Wharf is Ri Ra’s Irish Restaurant & Pub. The main dining area’s second floor presents an enclosed year-round panorama of the bustling Casco Bay Lines ferry as island residents commute out to sea on their way home. Right below Ri Ra's, Flatbread Company offers the same views and serves all-natural pizzas on their outdoor deck.


Portland’s waterfront dining has the happy benefit of being within steps of each other - you can experience them all in one night if you wish! Start with apéritifs at Ri Ra’s, move on to appetizers at Flatbread, then entrées at DiMillo’s, followed by a nightcap at the Porthole, and then end the evening with coffee and dessert at Becky’s... unless it’s a late night, in which case you can have breakfast when they open.


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Portland, Maine
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