Town Memorials | Winthrop, Massachusetts
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Town of Winthrop
Sesquicentennial Commemorative Book

(original available at the Winthrop Public Library)

Early Development of Winthrop

As noted in the foreword, the development of our peninsula began with the allotment of land for farms to fifteen men. Few if any of these men ever lived here, but their farms prospered. Before 1660, many of the original land­owners had sold their farms or abandoned them as they left the area. By 1690 there were only four farms on our peninsula, which were owned by Deane Winthrop and three members of the Bill Family, James, Joseph and Jonathan. The area from Cottage Hill north to Belle Isle Marsh remained as four to six farms until about 1800 before any major developmental changes took place. The areas South of Cottage Hill, known as Point Shirley, saw a number of business ventures pursued starting in 1753 and continuing through 1869. The development of each section of Town will be outlined with numerous pictures showing early houses, streets, hotels. rooming houses, clubs and the stations of our beloved railroad.

Center Development

The Center area was originally made up of various portions of the three Bill farms of the late 1600's. While the farms passed out of the Bill Family by the early 1700's the area remained relatively intact in the form of four to six large farms until about 1800. In 1805 the first schoolhouse was constructed where the current Police Station is located and in 1834 the first church was constructed near the Junction of Winthrop Street and Madison Avenue.

In 1839, the bridge to East Boston from Main Street was opened and new families began to move here. The Belchers, Floyds and Tewksburys -- who had married into the Bill Family -- were already here and increasing in number. Various clusters of homes were built in areas at the center of town to house these new families. As the population of school children grew, schools were built not only on Pauline Street but also in other areas of Town.

The Center section of Town became the early governmental and local business area. With the building of the first Town Hall in 1856 on the site at the previously mentioned school, the Library in 1898 where Sam Belcher's cows used to graze, the first Hose Company in 1885 on Pauline Street followed by the Center Fire Station in 1898, the current Town Hall in 1929, numerous other public buildings, the seat of our government became firmly entrenched in the Center. Over time, the businesses in Town spread out to the other sections of Town to better service the residents. The first Hospital owned and operated by Dr. Metcalf on Winthrop Street opened as a fifteen bed facility in 1900. The second sixty-five bed Hospital was constructed on Lincoln Street in 1930.

In 1910 the Pleasant Park Yacht Club was organized with their first club­house being erected on Pleasant Street in 1911. The building was enlarged in 1916 and, after their 1958 fire. was replaced with the current modem Clubhouse.

Court Park and Cottage Park Development

The western side of our Town was originally part of the Bill Family farms and remained as farm land 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 1820 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 1800, 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 un 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 Plummers, Bartlett's in-laws, built their home on Plummer Avenue.

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 on the old Sproule Estate at the foot of Plummer Avenue.

Highlands Development

The two hills of the Highlands section of Winthrop were originally part of the 1636/1637 allotments by Boston to William Pierce, Thomas Buttalph, John Sanford and William Aspinwall. On October 26, 1649, the farm was conveyed to Deane Winthrop. By the mid to late 1600's, Deane became the owner of the entire highlands as well as the Beach and Point Shirley areas. This was then known as the Winthrop Farms where Deane lived until his death in 1703/1704. His family continued ownership of the Deane Winthrop house until about 1750.

The Highlands, from Summit Avenue on Floyd's Hill to Grover's Cliff just beyond Prospect Hill, was purchased by the City of Boston in 1866 for the purpose of building an Insane Hospital. It was called the “City Farm” and subsequently deemed a poor location for such a facility being so far from the City and so close to the ocean. Instead the Hospital was built in Danvers and the Winthrop area lay dormant. As was the existing custom, this land continued to be used by the public for bird hunting. There used to be a fresh water marsh called Coomeys Pond near the comer of what is now the junction of Grover's Avenue and Nahant Avenue. A small cabin called Gove's Shanty was nearby where the men of the town often gathered in the evening to fish, tell stones and have a nip or two. In 1883 the entire City Farm was purchased by William Rice who had it surveyed for building lots and started developing the area.

In 1875 the southern side of Floyd Hill, was surveyed for building lots and Almont, Locust and Shirley Streets began to be developed. The area was called Floydonia since a number of Floyd families lived along Revere Street and on the hill crested by Summit Avenue.

Then in 1890/1891 the Fort Banks area and Grover's Cliff (later called Fort Heath) were acquired by the United States Government and the two forts were constructed.

In 1914. the Highland Yacht Club was formed and a clubhouse built on Nahant Avenue by the water. The club remained active into World War II at which time the building was used for a U.S.0 entertainment center. The clubhouse later became and still is a private residence.

Beach/Cottage Hill Development

The Beach and Cottage Hill Section of town was originally part of the Winthrop Farm, which remained in the Winthrop Family until the 1750's. While four houses were built on Shirley Street in the 1840's and 1850's, this area did not begin to develop until the 1870's. John Tewksbury built one or these houses in 1853/1854 at northern base of Cottage Hill and today it is the rear portion of the Inn at Crystal Cove.

At first a couple of summer tent encampments were set up near me beach where a few families from inland could enjoy the ocean breezes. Then in 1875, Dr. Sam Ingalls purchased 43 acres along the beach and laid out a summer colony of seaside cottages which he called Ocean Spray. All the streets were identified with nautical names that are still with us, Neptune, Mermaid, Coral, Trident, Sea Foam, Wave Way, Pearl and Dolphin. Many of the original cottages at Ocean Spray were of the same general design and, although somewhat modified, can be seen today. All deeds for the lots contained a prohibition clause, which is no longer enforceable, to prevent drinking in the colony.

Shortly thereafter. the section of the beach from Ocean Spray to Cottage Hill was purchased and named Atlantic Wave. In this area. the Tewksbury Memorial Pavilion was erected on Tewksbury Street in 1887 for summer services.

In 1878, Cottage Hill was purchased and then in 1882 surveyed for house lots. In 1883, William Rice purchased Cottage Hill and had Whitman & Howard lay out the streets, as we know them today. Also, in 1883/1884, access to the area was improved by the construction of a bridge from Washington Avenue to connect with Shirley Street at Delby's corner.

In 1886, the clubhouse for the newly formed Great Head Yacht Club (1884) was built behind a pier at the end of Tewksbury Street. It was subsequently moved in 1890 to the current location and renamed in 1890 as The Winthrop Yacht Club. The present clubhouse was built in 1904 after a fire destroyed the earlier building.

Point Shirley Development

That area of our peninsula known as Point Shirley was the first portion of the original Winthrop Farm to be purchased tor other than farming purposes. In 1753 a group of Boston businessmen acquired the Point from Joseph Belcher and established a fishery there, which at Its peak had 300 people living in the housing built for its employees. At the grand opening of the fishery, the area officially received its name in honor of the then Royal Governor William Shirley. Two of the homes constructed in 1753 and 1756 are still used as residences on Siren Street. While the business operated until 1763, some of the buildings used were used in 1759 to quarter British Troops. In 1764, they were reopened for use as an Inoculation Hospital and then again in 1767 to provide shelter for Acadians who had been removed in exile from Nova Scotia.

On April 19, 1775, a band of seventeen local patriots constructed a small stone wall at the top of the hill by Hale Avenue to serve as a fort, and stood guard for thirty days as the Revolutionary War broke out in Lexington and Concord.

In 1808 Russell Sturgis bought rights to Point Shirley and in 1811 opened a salt works, which continued in operation until about 1840. Orray Taft built his famous Taft's Hotel and Restaurant in 1830 where Maryland, Townsend and Otis Streets are now. Following a fire in 1851, the main structure was rebuilt and the business flourished until 1889 when the remaining buildings were then used as the Point Shirley Club up through the 1920's. A Greek Club/Restaurant then occupied the building until it was razed in the 1940's for house lots.

In 1844, the Revere Copper Works was established. This industry continued through the Civil War and finally closed its doors in 1869. Forty acres of their land were sold in 1883 for the development of house lots and the resort business began.


In 18S2 Winthrop was just emerging from its 220 years as a small farming community. The first bridge to East Boston had opened in 1839 and in 1841 the first stage and express line began running between Maverick Square in East Boston and Taft's Inn at Point Shirley. This stage line exchanged ownership several times until it ceased operation in 1873. The Winthrop Railroad Company was created in 1861 but it wasn't until 1872 that tracks were laid and the horse drawn trolleys were actively put in use. The car barns and stables were located on Revere Street where the Marketplace stands today and the trolleys ran from Taft's Inn up Shirley Street to Revere Street to Magee's Corner down Winthrop Street to the intersection with Pleasant Street and Washington Avenue where they proceeded up Pleasant Street to Main Street and then out of town. In spite of financial problems, this and a few other stage lines managed to provide service, in varying degrees, to our residents through 1888.

The Boston. Revere Beach and Lynn Narrow Gauge (three-foot-wide tracks) Railroad first operated in 1875 with hourly service. In 1877, the Narrow Gauge entered Winthrop and, known as the “Peanut Train,“ ran only from Winthrop Junction (Orient Heights) to Buchanan Street. In 1878 the line was extended across the marsh where the golf club is today and by 1885 was completed to Point Shirley. In 1880 the route across the links was relocated along what is now Veteran's Road. A standard guard railroad track from Lynn through Revere was extended in 1882 through the Highlands to Point Shirley by adding a rail to the narrow gauge track and sharing one of their rails. Only one train traversed this track from Lynn and that was on August 5, 1882. The operation of this line hadn't really begun to get started when a storm in 1885 washed out some of its tracks and the operation closed down. By 1886 the Narrow Gauge Line took over the operation and the loop around town, with its nine stations, was completed in 1888. This sing1e-track loop was double tracked in 1903 and Winthrop finally had permanent reliable. transportation to the East Boston piers and thence the ferry-boats to Boston.

Due to the increased use of automobiles, the operational cost of the ferry­boats for the reduced number of passengers became difficult to deal with. In 1928 the railroad was electrified to reduce costs, but on January 27, 1940, the last train made its run to Winthrop. The Narrow Gauge Railroad is nostalgically remembered for its smooth efficient ride and delightful sail across the harbor on the paddle wheel ferry-boat. Once the trains ceased operation, the transportation void was immediately filled by Rapid Transit buses.

It should be noted that briefly from 1910 to 1928 there was a privately owned little electric trolley that ran from the Winthrop Beach Station at the corner of Washington Avenue and Shirley Street out to Point Shirley.

During its heyday from 1880 to 1940, the train line through Winthrop followed the path as shown on the accompanying map. Pictures of the nine stations that served the line within our Town are also provided.

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