One of Winchester’s four former train depots was actually a house built next to the tracks at Cross Street whose second story was used as a waiting room.

WINCHESTER — Recalling the earliest days of the railroad, an elder resident wrote in 1885 that “we boys would gather and watch for the nose of the iron horse as it appeared from under the Mystic Station Bridge, on the south, or from the other bridge then standing at about the same stance, on the north. This was the signal for a scramble of the youngsters, who would rush to swing the Gates open, hold them till the train passed, and then, with a shout, close them again. In our estimation, this was a very important, as well as exciting, occasion.”

The railroad was exciting. It was the catalyst for industries to locate near the convergence of the railroad, river, and main road. Industry brought workers. The growing population needed tradespeople. By mid-century the village became a town.

After the railroad was built in 1835, a line was added in 1844 (the Woburn Loop) which branched off north of the gates and paralleled Main Street into Woburn center. An 1846 newspaper advertisement identified the Winchester stops: Bacon’s Factory, South Woburn, and Cutter’s [near Salem Street].

The first two stops were shared with the main line. All three were located at industrial sites, since the anticipated demand for rail transportation was for freight. But soon passenger use became profitable. The ease of transportation encouraged Boston businessmen to settle in the suburbs, and the town continued to grow.

The railroad offered jobs to many, on the trains and rails, in the workshops and offices, and at home. In fact, some of the town’s most familiar residents were to be found at the railroad stations.

Nathan Jaquith, second station master, for example, was remembered about 40 years after the fact “as a solid and reliable man, affable in his manners, and highly esteemed by the railroad managers and popular with the boys.” His duties also included baggage man and gate tender.

In the beginning, the center station was located near the Lyceum Building. Following heated debate, the railroad built a new depot in 1872 at the site of today’s Waterfield lot. It had separate men’s and women’s waiting rooms, ticket office, baggage area, and, starting in 1884, the telegraph office.

Before the century’s end, Winchester had not one but four railroad stations and four station agents.


During its first decade, Winchester gained a depot at Mystic next to the outbound tracks at Bacon Street. Most of the two-story structure was a dwelling house, with one room in the northeast corner set apart for the convenience of passengers.

In the 1860s, Oliver Randall and family were in residence there. In 1931, resident Henry C. Robinson, head of the Southern Division of the Boston & Maine and a railroad employee since 1870, described a trip in the 1860s, writing that “Mr. Randall is a carpenter by trade and is employed as such in the railroad carpenter’s gang. Being away all day, the station duties are carried on by the family.”

The Mystic stop originally served Baconville, the neighborhood around the Bacon mills, but increasingly was used by passengers from the burgeoning residential developments nearby.

Because riders headed to the Mystic Park Station for the trotting racetrack in Medford were erroneously going to Winchester’s Mystic Station, the name was changed about 1897 to Wedgemere, a name shared with a housing development on the other side of Church Street in The Flats, though neither was contiguous to Wedge Pond.

By Jan. 11, 1901, when a photograph was printed in The Winchester Star, a new depot had been built on the west side of the tracks. Ralph Cardinal, the station’s third agent-operator, worked there from 1908 until it closed, over 50 years.

“He literally served thousands of commuters,” the Star stated, “knowing many of those he served by name and being popular with the commuters generally.”

In the early years, Cardinal would arrive before the first train, known as a “marketman’s train,” at 5:56 a.m., walking every morning either from the Symmes Corner trolley stop or, after moving, from his Russell Road home.

“In the earlier days of the station, the agent handled baggage there and also shoveled out the station platforms after snow storms. Things were rugged then.”

Highlands & Cross Street Stations

During the 1870s, residents in the northern part of Winchester desired a stop on the main line. The railroad was reportedly willing to stop there but unable to fund a depot. So Aaron Bell bought land next to the tracks and built a house. The tracks being raised up about 12 feet from the street on an embankment, the house’s second story was used as the Highlands Station.

The house was originally home to the family of George W. Richardson, the first station agent. A section foreman for 51 years, he did not remain at the station. Not all succeeding Highlands station masters lived in. Lewis Neville did, until apoplexy carried him off in 1895, but Edwin Chase, station master from 1897 to 1930, did not.

Cross Street got a second station in 1893 when the Woburn Loop stop was moved up to Cross Street and a new depot was built on the inbound side of the tracks. At that time, the small one-story building was staffed by a station agent. By 1931, it had been replaced by a three-sided frame shelter, employing no agent or crossing tender. In 1955, it was replaced with a concrete shelter which stood through the mid-1980s.

Similarly, the B&M, which purchased the Highlands property after Bell died in 1910, replaced the station house with a shelter in the early 20th century. By mid-century, increasingly fewer trains were scheduled to stop there. In 1964, the B&M still listed the Highlands as a stop but then sold the lot. In fact, it sold all three stations on the main line.

Waterfield and Wedgemere

When the overpass was constructed in the mid-1950s, the railroad was seeing business drop off due to increased trucking and commuting on the highways. Yet it built two new stations in Winchester instead of one and did not cut service.

“Half the corporation’s officers lived in Winchester; they would not cut their own throats,” historian Bruce Stone wrote. It is popularly held that one or more corporate officers living in Winchester personally wanted Wedgemere kept open.

Winchester has indeed been home to B&M executives. Back in 1914-1926, the president of the B&M, James H. Hustis, lived on Church Street. Robinson, a native, lived on Winthrop Street until the mid-1930s. During the 1930s and 1940s, the vice-president in charge of operations, John W. Smith, lived on Sheffield Road. In 1943, his name was on a list of 19 prominent B&M employees printed in the Star.

Although Smith left in 1950, other executives on that list were in Winchester when the overpass project started, including Edward J. Gallagher, treasurer of the B&M and a resident of Wildwood Street.

Despite both stops being saved, the B&M sold the depots a few years after opening them. Private ownership of the Wedgemere depot was troubled from the start. By 1964, the property had already deteriorated. The owner, a construction company, owed back taxes and was looking to sell the property. Town Meeting debated purchasing it and eventually opted not to take it by eminent domain (which meant paying the assessed value) but rather approved an appropriation to cover a $500 payment to the seller plus the back taxes.

In 1982, the town took over the center depot. The town was engaged in developing a parking program for the downtown and had a 90 percent matching fund (about $2M) from the Commonwealth. Spring Town Meeting approved $120,000 (and the state added $275,000) to purchase the railroad station and Waterfield parking lot. Although more was appropriated to build a parking garage at the site, such a project has yet to be approved.

Thus, while the history of station masters concluded long ago, the history of the station depots continues.

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