Court Park and Cottage Park

The western side of our town was originally a part of the Bill family farms and remained as farmland until the early 1800’s. One of the original four mid 1600 farmhouses was located on what is now Johnson Avenue near Bellevue. It was later occupied by John Tewksbury and existed until the mid 1800’s. His son John Sargent Tewksbury built a home about 1836 nearby on Somerset Terrace. This house was cut in half and one section relocated around the corner on Somerset Avenue where it remains today. In about 1790, Captain Joseph Belcher built a home near the water where the end of Sunnyside Avenue is today. This building became known as the Parliament House since many of our early governmental meetings were held there. Following a fire in 1890, the building was razed.

Shortly after the 1839 bridge to East Boston was constructed, several estates were established in this section of town. First Judge Edward G. Loring and the Honorable George B. Emerson bought the 48 acres in Court Park and built their two estates in 1847. During the years that followed, they had over 1500 trees planted in this area many of which are still standing.

In 1850, Charles Bartlett and Hiram Plummer came to town. Bartlett built his home at about 175 Bartlett Road which was subsequently bought by Orlando Belcher in 1884 and greatly enlarged to become the Cottage Park Hotel. The Plummer’s, Bartlett’s in-laws, built their home on Plummer Avenue. A picture of the Cottage Park Hotel as it appeared in its “Hayday” is shown below.


With the death of George Emerson in 1882 and then Judge Loring in 1890, the Court Park area became first a riding academy and then Winthrop’s initial golf course. The roads in the Court Park section of town were laid out in 1896 on the fairways and hence the area became known as the maze.




In 1902, the Cottage Park Yacht Club was established on the old Steamboat pier at the end of what is now Orlando Avenue. The Steamship Line ticket office was the first clubhouse. The second building opened in 1908 and burned to the ground in 1926. While the present clubhouse was being constructed, temporary quarters were set up the old Sproule Estate at the foot of Plummer Avenue.