To judge the sizes the medallion sections each measure 1-9/16'' wide. They appear to be in mint unused condition as pictured. Below here, for reference is a little additional information on Portland, Connecticut:
From Wikipedia, the free encyclopedia
Portland is a town in Middlesex County, Connecticut, United States. The population was 8,732 at the 2000 census. The town center is listed as a census designated place (CDP). It is situated across the Connecticut River from Middletown.
Brownstone quarried in Portland was used in the construction of Hartford's Old State House in 1796. The vast majority of the brownstone buildings in Connecticut including College Row at Wesleyan University and the Long Walk at Trinity College, as well as the famous brownstones in New York City were built with brownstone from Portland's quarries.
The Wangunk ''Big Bend'' Native American Indian tribe lived in the area before European settlement. Their name referred to the bend in the Connecticut River which curves around half of the town's perimeter.
Settlement to the nineteenth century
The first European settlers came to Portland in the 1690s. They were attracted by brownstone, which was used both for construction and for gravestones. Proximity to the river meant that the stone could be transported far and wide, and the Portland brownstone quarries supplied to New York, Boston, and even San Francisco, Canada and England. By the 1850s, more than 1,500 people were employed in the quarry industry. More than 25 ships transported the stone. By the 1850s, shipbuilding became more important as an industry, and the economic center of town shifted toward the Gildersleeve area. Immigrants from Ireland, then Sweden, then (to a lesser extent) Italy came to town to work the quarries.