Today’s sandwich is the “Ham Italian” from DiPietro’s Italian Sandwiches. It combines ham, American cheese, raw diced onion, green peppers, tomatoes, Sicilian olives, pickles, salt, pepper, and oil on a soft hero roll.
Location: 171 Cumberland Avenue
Price: $4.25 (Large)
Notes: DiPietro’s is a tiny, hole-in-the-wall Italian sandwich shop, with a long-standing family history in Portland reaching back to Portland’s great bloody “Italian Sandwich Wars” of the early 17th century. The tiny shop, which consistently enters most discussions of Portland’s “Best” Italians, has been cranking out Italian sandwiches and pizzas for generations, as well as the usual complement of Humpty Dumpty potato chips, soda, and creme horns. The service was super fast, if not a tiny bit standoffish.
The Italian sandwiches at DiPietro’s are served on the customary soft white Italian loaves, that are almost like giant, oversized hot dog buns. The rolls are flayed open wide, with the ingredients stacked on top, open-face style. Our bun was a little on the stale side, and slightly dried out. The tomatoes were pretty crunchy an unappealing, but I blame that more on the time of year than on the sandwich itself. We really liked the long, thick slices of sour-ish pickles, as well as the thick shards of green pepper. The ham and cheese played as little a role as it ever does in this classic Maine sandwich. The real wildcards in DiPietro’s version were the olives. Instead of the sliced Kalamata we have had elsewhere, DiPietro’s seems to use oil-cured Sicilian black olives. These little shriveled bombs of flavor aren’t my favorite thing when eaten alone, providing much stronger, saltier flavor than I am used to with brined olives, and taking a little bit away from the overall “freshness” that I associate with an Italian. When combined with the rest of the sandwich, though, these olives provide a muskier, pruney addition that I quite enjoyed.
Overall, DiPietro’s is cranking out delicious, wildly inexpensive sandwiches, the way they have been for at least 60 years. While not our favorite version of this sandwich to be found in Portland, they are much, much better than many chains, and their unusual choice of olives makes DiPietro’s worth sampling.





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We're Jillian and Malcolm. We cook comfort food from around the world, designed to make you feel right at home, wherever you are. Join us as we explore Maine's vibrant food culture and cook New England's classic dishes, as well as our favorite recipes From Away. 












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