My first stop was for a "Maine Quarter Pounder" at Bayley's Lobster Pound where one of the world's first lobster rolls was created and today is the home of biggest (and tastiest) lobster roll I've come across in the U.S. Since 1915 when Ella Bayley began selling the leftover lobsters her husband had caught to feed her and their four sons out her kitchen window, the family has sold over 30 million pounds of lobster! (See her and Steve pictured, below left.) For around $7 (prices fluctuate) I got about a quarter pound of fresh, heavenly lobster meat, mixed with a touch of mayonnaise, and heaped onto a simple hot dog roll. Bayley's also ships live lobster and other specials throughout the US via FedEx packed with seaweed to survive up to 36 hours. Starting around $80 from Bayley's.
Next I headed to the Old Orchard Beach Pier, honky tonk capitol of Maine and home of The Original Pier Fries (pictured below left). Their heaping box of hand crinkle-cut fries, doused them with the recommended combination of white vinegar and salt, are some of the finest fries imaginable.
Going through the squeaky screen door of the Harbor Fish Market, surrounded by buckets of fresh local Damariscotta Oysters, Little Neck Clams, iced bins of Flounder, Haddock, Monkfish, and Swordfish— not to mention a full wall of green tanks housing live Down East lobsters—felt like a time capsule of old New England. Their impressive smoked fish department often carries Finnan Haddie, a smoked haddock fillet that is almost impossible to find outside of the UK or Nova Scotia. Call 1-(800)-370-1790 (ext. 3) 48 hours before you want your order shipped anywhere in the U.S. map) my search came to a happy end. In addition to a huge selection of amazing hand-crafted boules, focaccias, rolls, muffins and quiches, I found the best baguette I have ever tasted outside of the 4th arrondissement. The owners of Standard Baking Company actually trained at boulangeries in Paris before returning to Maine to recreate the perfect crisp outside and delicately soft inside that is characteristic of the perfect baguette. They also make wonderful pain au chocolat as well. You can reach them at 1-(207)-773-2112. Amato's Sandwich shops. "Italians" as Mainers call them, aren't meant as a boastful claim to continental authenticity—for that you're better off in the Campi dei Fiori. Instead, the name refers to a special Maine invention created around 1903 when immigrant Giovanni Amato added vegetables, meat, and cheese to the rolls he sold to Portland dock workers. The is an oversized baguette-shaped piece of bread with the texture and consistency of a hot dog roll, filled with ham, cheese, raw onions, peppers, pickles, tomatoes, and regular vegetable oil.
Perched atop the rocky entrance to Portland Harbor between two historic light houses is the Lobster Shack Restaurant. Famous for delicious fried clams, seafood, and one of the most stunning outdoor eating areas (intermittently sprinkled with drops of sea spray from the nearby crashing surf), they are also home to one of the best Maine Whoopy Pies. Spelled Whoopie in Pennsylvania (the other location it was supposedly developed), the Lobster Shack's pie filling is made of a rich near-butter whipped cream surrounded by moist chocolate cake-like disks.