Landmarks of Orient Heights include the "Madonna Shrine:" it is the headquarters and National Shrine of the Orionine order, founded by St. Luigi Orione. A third of a mile away towards the west, a huge, lighted cross stands dramatically on Orient Heights. It is one of Boston's most visible and well-known landmarks. Despite the cross's assumed relationship to The Madonna Shrine, it instead marks the site of the second battle of the Revolutionary War, the Battle of Chelsea Creek (May 27, 1775).
The hill of Orient Heights was once called Hog's Island; then it was later renamed Breed's Island. The hill is one of the five islands that comprised old East Boston.
Well into the 20th century, Italian and English were still spoken in roughly equal amounts in Orient Heights. It is documented that, as recently as the 1940s, Masses at St. Lazarus Church in Orient Heights were delivered by Pastor Luigi (Louis) Toma in Latin, Italian, and English.
One of the most recognizable icons of East Boston is the -high statue of the Madonna. The Madonna Shrine, at the top of Orient Heights overlooking the airport and Downtown areas, is the national headquarters for the Don Orione order. Constructed in 1954, the statue is a full-size replica of one at the Don Orione Center in the Montemario district of Rome, Italy. It was constructed in 1954 by Jewish-Italian sculptor Arrigo Minerbi, who wanted to show his gratitude to the Catholic Church for having shielded him and his family from the Nazis during World War II. Across the street from the Shrine is the Don Orione Home, a nursing home which, like the Shrine, was founded by the Don Orione priests. The Shrine and Home were founded in 1951 by the Don Orione priests, led by Fr. Rocco Crescenzi, who was sent from Italy for this purpose. Crescenzi had been an errand boy for St. Orione himself. In 2007, the nonagenarian Crescenzi was still active at the Home and Shrine.
The main thoroughfare through Orient Heights is Bennington Street, and the principal intersection ("Orient Heights Square") is that of Bennington with Saratoga Street.