Whether played by informal pickup teams or formally organized clubs, sports have flourished in the town of Winchester. Clubs and teams both youth and adulthave been formed. Indoor recreational centers have offered recreations such as billiards, bowling, and curling. The schools have offered a variety of sports and extra-curricular activities, although they are outside the scope of what follows here—with the exception of the team name Sachems, shared with a men's team of the 1940s.

Residents have also enjoyed watching young people from town compete at the Olympics and other tournaments or go on to professional athletic careers


After the Civil War, the public was reportedly “running wild” over the game of baseball. “The youngest boy hardly able to handle a bat, up to full-grown men, are all full of this one idea…. The community has base ball on the brain and are joining clubs in every town and village almost…. Many serious results are likely to ensue from playing this game,” including injuries and the moral effect of betting.1

Nevertheless, Winchester residents enjoyed their ball games. The first known game played in Winchester, recorded in the pages of The Middlesex Journal, was played in November 1866 by the Everett Base Ball Club of Winchester and the Middlesex Base Ball Club. The former won 45 to 19. The town had several early teams. In 1868, it had the Independent Base Ball Club, the Mystic Club which played the Stars of Woburn in June 1868 and the Arctics of East Woburn in October, and the Clipper Club which was beaten by the Eagle Club of Woburn by the score of 31 to 26 later in October.

The ball clubs played frequent games with teams from other towns on Bacon Field near the corner of Church and Bacon Streets (through which Stratford Road now runs). Bacon Field remained the arena for outdoor sports from 1874 until the development of Manchester Field in the 1890s (pictured below). As the Town laid out more fields, baseball spread to them, also. When Leonard Field opened in 1921, it had a baseball diamond. From the 20th century into the 21st, baseball has also been played at McDonald Field, which opened in 1925, Ginn Field, laid out in 1938, Mullen Playground, and the West Side Field, as well as school playgrounds.


In the early 20th century, summer baseball was possibly the most popular sport. Town teams played one another and teams from other towns, even advertising in the Boston papers that they were looking for games. Teams were formed by neighborhoods, by businesses, and by organizations. During the Great Depression, one popular team playing during the summers took on the name, the Millionaires. 

“In an era when baseball reigned as the national pastime [early 20th century], Winchester boasted its own semi-professional team. Sponsored by the Winchester Baseball Association and managed by George D. LeDuc, the town team played opponents from other communities or, on occasion, even the likes of the Philadelphia Colored Giants and later the famous ‘House of David’ nine (which sported bearded players). Games at Manchester Field drew up to 6,000 and the annual Labor Day doubleheader against Woburn was one of the big events of a Winchester calendar.”2

Little League was organized in 1952 with four teams and 60 boys. By 1960 there were 20 teams with 300 boys playing ball. In 1955, the Winchester Yankees won the Little League World Series at Williamsport, Pennsylvania. In 1956, they made it back to the finals in Williamsport. Also in 1956, a Babe Ruth League for the older boys began. A new ‘Big League’ started in 1968 and, in its first year, represented New England in the national championships. “By 1972 the Little League had over 600 players on 38 teams watched by 15 administrators and 162 managers and coaches.”3 [Read more: Branch Russell, Robbie RobinsonHod Ford]


Possibly Winchester's first formal sports club, the Myopia Club began with with a group of boys who used to play together around Wedge Pond where they could go boating and where they built a tennis court during the 1870s. When they took up baseball, they took on a name. Since they were all short-sighted, they chose the name Myopia.

The club acquired a clubhouse on what came to be known as Myopia Hill, built by a member's father-in-law. Adjacent to it were stables, tennis courts, a shooting box, and acres of woodland.

When the club incorporated in the fall of 1879, its stated purpose was "for encouraging athletic exercise and yachting and establishing and maintaining a place for the use of a reading room and for social gatherings."

In 1882 more members were interested in hunting than in playing ball and changed the name of the club to the Myopia Fox Hounds. In 1883, after just four years on the hill, the club gave up the hillside house and grounds and moved to other grounds. When the Brookline Country Club, generally known as the oldest county club in the country, formed in 1882, its members included a number of Myopians. While maintaining a separate existence, for years the Myopia Club had close relations with the Brookline Country Club, hunting from there. As parent to the Brookline Country Club, it is therefore justifiable to call the Myopia Club in Winchester the first country club, though the club in Brookline was first to take the name. [Read more: Myopia]


Reportedly, it was the boys of the Myopia Club who laid out the first lawn tennis court in town. During the 1870s, the boys played together around the Frederick O. Prince home on Wedge Pond (in the Wedge Pond Road area), where they could go boating and where they built their tennis court. After the club moved to Myopia Hill, they had tennis courts on their club grounds there.

Back at Wedge Pond, tennis continued. The Wedgemere Tennis Club was formed in 1886 and lasted at least eight years. This group had six lawn courts (later described as two cinder and four grass courts), a club house, and grounds. Membership was open to both men and women. Club members not only played one another but also other towns in the Middlesex County League, which held occasional tournaments in Winchester. That Boston’s athletic good store Dame, Stoddard, & Kendall advertised a racquet called the Wedgemere Expert may indicate the reputation of the club.

The club struggled with funding and, during the winters, put on shows to help raise money. Though the shows were reportedly very popular—in fact they inspired the canoe club also to put on fund-raising shows—in 1893 a snowstorm brought disaster when it fell on the night of the club’s most expensive production. [Read more: Minstrels]

At about the time the Wedgemere Club was winding down, the Calumet Club built a club house on the other side of Wedge Pond (1892) with an adjacent tennis court. The Winchester Boat Club also put tennis courts next to its new club building, built in 1901, as did the Winchester Country Club after acquiring the site for its golf course and clubhouse in 1902.

In 1923, a local tennis club, the Benedict Club, formed and joined the Old Colony League. It used private courts at Park Ave./Governor’s Ave. until those courts were lost to a housing development. That club was succeeded by the Winchester Tennis Association which opened its first tournament in May 1929. The WTA used the new public courts. 

Packer courtsIn 1917 the town bought land for the courts (and adjacent playground) at Wedge Pond, the site of the old Wedgemere club and another group called the West Side Tennis Club. Four courts were originally planned, and work on them began in 1922. Expanded over time to 8, 11, and later to 15 courts, the site is now known as the Packer-Ellis Courts, after park commissioner William S. Packer, a minister, newspaper editorialist, and tennis enthusiast, and Donald R. Ellis, a part-time town employee who assumed maintenance of the courts and was president of the Winchester Tennis Association (1974). Courts were also built during the early twentieth century at Leonard Field and the Loring Avenue Playground, now MacDonald Field.

Tennis womenWhen new, the WTA joined the Old Colony League and began a continuing history of both adult and junior local tennis tournaments at the Packer-Ellis Courts.

The town also has school tennis and indoor tennis, once including the National Women’s Indoor Tennis Championships which drew Billy Jean King to Winchester.  [Read more: Champions on Winchester Courts Made Tennis History­]


The introduction of golf to Winchester encouraged the formation of yet another club. In 1897, a group of golfing enthusiasts decided to form a club. The Golf Club was originally a small group which rented a tract of vacant land belonging to Edwin Ginn along Pond Street and Woodside Road. The first president of both the golf and country clubs was Rev. John Suter, rector of the Episcopal Church. Five men formed the executive committee in Nov. 1897.

Country ClubAfter five years, the club was incorporated as the Winchester Country Club. In 1902, it bought the Stephen Swan estate at the base of Myopia Hill at the Arlington-Winchester line, used the Swan house as a clubhouse, and laid out a nine-hole course, as well as tennis courts.

As the game of golf flourished and club membership grew, the course was expanded to 18 holes. The clubhouse was enlarged and renovated by F. Patterson Smith. Club sports expanded to include tennis, bowling, and curling.

A full-length history of the Winchester Country Club was published by the club on the occasion of its centennial. 


The Aberjona River and Mystic Lake have long been inviting to boat lovers. Formerly, however, Wedge Pond was a popular boating site. At the close of the 1870s, there were once 25 rowing and sailing craft there. 

CanoeAbout 1886, the Shuh-shuh-gah Canoe Club was organized and built a house on the riverbank near the Bacon Street Bridge. In 1889, the club house was enlarged and out-of-town members were admitted, including Sylvester Baxter, “father of the metropolitan park system.”4

A few years after 1900, when the Winchester Boat Club was formed, the canoe club became inactive and the house was removed. The Boat Club built a clubhouse in 1901 on the banks of the Mystic Lake. Over the years, it was enlarged, repaired after hurricane and fire, and in the 1960s was provided with a swimming pool.

Boat ClubThe Boat Club carried on with canoeing, both paddling and sailing, and established two challenge cups (now retired). The last of the club-owned canoes were sold in 1949. In the 1930s, sailboats of various types began sailing on the lake and continue to be seen there.


Residents have long enjoyed swimming, the major difficulty arising in the late 19th century with industrial pollution of the water. Each of the three beaches, at the Mystic Lake, Leonard Pond (pictured below), and Wedge Pond have had water-quality problems, leading to their being closed at various times.

Leonard swimmingIn 1923, the Red Cross and Park Department cooperated on an annual swimming carnival. Though the term changed to “swim meet” in 1944, the tradition of classes and competitions at one pond or the other continued for decades. Since the local chapter of the Red Cross left town (about 1978), swim activities have been the responsibility of the Recreation Department.

Proposals to build indoor pools at the high school or junior high (middle school) have all been defeated, essentially due to cost. On more than one occasion, groups have formed to promote the construction of an indoor pool, either as part of a community center or as a dedicated pool, but none has yet succeeded. [Read more: Beaches]


Not only a utilitarian part of Winchester, horses were also kept and used for recreation and sport. 

horsebackThe proximity of the Middlesex Fells has enabled recreational horseback riding in an open setting from early days up to the present day. “So everybody when they had a few dollars they went down and rode the horses in the Fells,” Bob Walsh (b. 1932) related. “That was a great sport. We had our own basketball games on horseback. You’d carry the ball and if somebody pulled you off then the ball was free and you had to get it and get it through a basket to get a point.”5

An indication of how popular horseback riding was may be gained from the fact that when Lorena Sanborn wished to raise the level of fund-raising to benefit Winchester Hospital, she began hosting horse shows. When the Sanborns left Winchester, the shows were hosted at Good’s Riding School grounds in West Medford for several years.

Originally Harry Good ran his school in Winchester, opening the Winchester Riding School at 676 Main St., next to Wedge Pond after WWI. In 1919, it was reported that “Winchester society girls have taken up riding as a popular pastime and demonstrate their skill on crisp October afternoons along the Fellsway.… Riding has also come to be favored by the high school students and every Saturday the riding school of Harry Good is thronged with merry young people.”6 About 1925 he moved his school to Medford.


In the fall of 1932, the Winchester Badminton Club was organized for adult residents and employees "to create and foster interest and skill in the game of badminton, to furnish diversion, to encourage sportsmanship and to promote good fellowship." Games were played in the High School and later Jr. High gymnasiums. Tennis enthusiast William S. Packer, along with the high school principal, Wade Grindle, were among the founding members. 

Also in 1932, badminton opened as an activity for the First Congregational Church’s men’s club, but it was the public group, which admitted both men and women, which endured.


When the town was not so highly developed, many open spaces were used for sports such as baseball and football. “We used to look for open lots and that’s where we played our football,” said Lane McGovern whose family arrived in 1932. “In fact there was an open lot right next to our house when we moved over from Arlington to Cambridge Street, and we played a lot of football there in the third and fourth grades. As you got older there was a lot of football in junior high and the first year of high school. There was a lot of impromptu after school football in an open lot behind the stone wall that is opposite the Crawford Memorial Methodist Church on Church Street. If you look across Church Street you’ll see a stone wall. A lot of houses occupy that spot now, but there was a tremendous, big space where boys in junior high would go to play football. The girls would line up to kid around and this and that. It was a social place, and it was fun to have that space.”7

“We created fun games,” Bob Walsh recalled. “Baseball was big. Football, sandlot football and sandlot baseball were very big. Everybody participated in it.”8  

The entire community enjoyed the school games. A traditional rivalry with Woburn at Thanksgiving time, started in 1891, is one of the longest known in the state. Passions have often erupted at football games, as witnessed by a game against Woburn in 1898. [Read more: A football game ruined in 1898]


Basketball has been not only a school sport but also one with adult teams. It was, in fact, a post-WWII group of veterans who first assumed the name Sachems. Most of the men had played for the high school and some for college teams and, as veterans, played well against other towns’ teams. In their first season, they won 12 out of 16 games. In their second season, the Sachems competed in the Greater Boston Basketball League and won the league championship in March 1948 after beating the Lexington Warhawks. 

During the summers of those two years, the Sachems had a team in the town softball league. At least three members played both basketball and softball.

Basketball has the distinction of being the first team sport for high school girls. In the first decade of the 20th century, while the boys had football, basketball, hockey, track, baseball, and canoe crew, the only team girls could play on was girls’ basketball. Attendance at the girls’ games was limited to parents and women, and a woman teacher was invariably present. 


The first known mention of cycling dates to 1869 when a report appeared in The Middlesex Journal that "The velocipede mania which prevails everywhere at the present time has suggested the having a rink in our town, for the accommodation of those wishing to learn this method of riding. Mr. Taylor has accordingly extemporized one near the centre, in the rear of the machine shop, which is much improved by many of our citizens." 

BicyclesMany residents have enjoyed cycling for pleasure and commuting since bicycles were invented. At certain times, bicycles have been actively promoted. During World War II, for example, Winchester became the first town in the country to receive a bicycle rack provided by a commercial railroad for those commuters conserving on fuel by riding bikes to the train station. In 1976, cycling was viewed as one solution to the energy crisis, resulting in the creation of a 2.4 mile pedestrian and bike path adjacent to the river, the Aberjona Bicentennial Bikeway. It began at the Winn factory (620 Washington St.) and ended near Ginn Field.9 By the end of the century, it was outdated and had fallen into disrepair. In 1996, the Winchester Greenway Initiative proposed a tri-community bikeway or greenway, linking Winchester, Woburn, and Stoneham. After many years of planning, negotiations, and appropriations, work on the Winchester section of the bikeway began in 2017.


Skating rinkOutdoor ice skating has been enjoyed at town ponds and, in the past, at ice rinks. In the 1920s, the tennis courts on Palmer Street were flooded during the winter for skating. Makeshift rinks at Shore Road Field, the old Skillings property (pictured right, now the Town Hall parking lot), and at Leonard Field were used. Discussions of a permanent rink to be built and owned by the Town were held but abandonned when the Universal Sports Arena was built in 1971 on Conant Road. After the rink was demolished in March 1988, the site was later developed for condominiums, leaving the town without a skating rink.


Though public bowling alleys and pool halls are a thing of the past, the Board of Selectmen used to issue licenses for both. In 1910 for example, there were pool rooms on the second floor of the Lyceum Building, at the Hotel Winchester at 620 Main St., and in a wing of a building also housing a grocery store at 94 (later 114) Swanton Street. These same areas of town have also had bowling alleys, the first fitted up in a commercial building opposite the train depot in January 1861. All such are now gone.

Some private clubs have had facilities for varying forms of entertainment, such as billiards and bowling at the Calumet Club, organized in 1886 from the Winchester Young Men’s Association. There were game rooms and a gymnasium (as well as a reading room) at the YMCA, which used the entire upper floor of the White Building for about 15 years after its construction in 1890. After the YMCA dissolved, the second floor of the building was then used for offices. 

From time to time, it has been suggested that the town build a community center. For example, in 1916 a proposal was put forward to build “a club house which could be used for a great variety of social and philanthropic purposes and contain a number of accommodations of which at present our town is sadly deficient.” The suggested site was Vine Street, bordering the pond, leading to the name Wedge Pond Club House. It was to contain a large hall, three small halls, a banquet hall, smoking room, kitchen and pantry, plus a swimming pool with dressing and locker rooms. And it would have a boat landing. Not only a recreation center, the building was intended to be a center of civic betterment work such as training girls to become child nurses. It was announced that enough rental contracts had been secured to pay for all the interest (on the bonds) and expenses for the first year. When asked for approval of the plans, the Board of Selectmen took no action.10

Following the end of World War I, one proposal to honor veterans was to erect a building suitable for athletic or recreational purposes on (the old) Manchester Field. It was to have an auditorium, field house, and rooms for the American Legion. It was defeated in a referendum vote. In 1954, The Fortnightly (women’s club) sent out a suggestion to 54 various clubs and organizations that they present to their members the subject of building a Community Club House on the former Skillings Estate as a memorial to the veterans of both World Wars. No club house was built.

The town had recreational facilities in its school buildings and opened these to the community. During the winter of 1940-1941, the town launched an adult recreation program in the old Wadleigh School and at the high school, including exercise classes, dancing, gymnastics, rug-making, and woodworking. Under different committees and departments, recreation programs for all ages continued to be held in school buildings.

Youth have had–and lost–recreation centers. In 1936, the Town began renting the old Methodist Church, then belonging to the New England Laundries. It was the scene of lectures, plays, concerts, and dances and had facilities for ping pong, badminton, pool, billiards, games for younger children, and sewing for girls. “The Centre is serving a definite community need in providing facilities for underprivileged boys and girls. Street corner gangs and rowdyism just do not exist in communities that provide facilities for supervised play and self-improvement,” the Winchester Star proclaimed in 1938.11 During World War II, girls met there to knit for relief groups. The Red Cross and Civilian Defense organizations used it to teach first aid. Limited funds for repairs and heat forced its closure in January 1943. High school kids got their own place in 1944, the Red and Black Canteen, by renting the Odd Fellows Hall on Vine Street. It had two pianos, a juke box, a Coke bar, and a game room with billiards, darts, checkers, cards, and a Ouija board. It lasted 18 months.

In 1946, the selectmen held a hearing on a proposal to establish a community center for young black people. An Army chapel at Fort Devens could have been moved to town land off Irving Street to be “a place where young colored people of the town could go for wholesome recreation and amusement.”12 While promoted by the current minister of the New Hope Baptist Church and some of its members, it was opposed by a former pastor and other members of the neighborhood who felt it could not be supported unless out-of-towners assisted, which they felt was undesirable. Residents of Irving Street also opposed it. This proposed club house also never happened.

In the 1960s, another proposal appeared to create a recreation center for youth and other civic events. This one would have been put on Leonard Field and would have been a complex including a pool, arts and crafts building, theater, shop building, field hose, and artificial ice rink. This proposal was simply too expensive.

Early in 1968, a gala party was held for the opening of a new youth center above the Purity Save-Mor. Converted from a bowling alley, it had a snack bar, two multi-purpose rooms, and a dance hall. It closed due to waning enthusiasm.

In the latter part of the 20th century, a Youth Center was established in the McCall Junior (later Middle) School. In 2004, a new proposal for a Teen Center at the train station appeared and was studied, but again never happened. At the same time, a new Community Center Advisory Committee again attempted to promote a new intergenerational sports facility with a pool, ice skating rink, field house, and fitness/training facilities. The favored site was Skillings Field. The plan was not adopted. As part of the high school renovation and Aberjona River flood-mitigation program, the field was studied, the fields realigned, and a parking area added. Suggestions to build a swimming pool there have conflicted with desires to maintain field space.


Joe Bellino, Heisman Trophy winning football player at the United States Naval Academy

Laurence Owen, winner of National US Ladies Championships and the North American Championships

Maribel Vinson Owen, Winchester native, nine-time national champion and the 1932 Olympic bronze medalist, a member of the World Figure Skating Hall of Fame and a three-time inductee in the United States Figure Skating Hall of Fame as a singles skater, pairs skater, and a coach

Maribel Owen, winner of National Junior Pairs title in 1956 National Pairs Championships in 1961. 

Alicia Sacramone, five-time Gymnastics World Championships medalist and 2010 Olympic silver medalist 

Irving Small, captained the American Olympic Hockey team in 1924 at the first Winter Olympic Games, held in Chamonix, France, when the Americans won the silver medal.

Gordon Smith, Winchester native, played on the 1932 Olympics team at Lake Placid, when the U.S. took the silver medal and went to Berlin for the Winter Olympics in 1936 and scored the winning goal in the first game that the U.S. team played on its way to winning the bronze medal in ice hockey.


Frank Garland Trott (1871 - 1949) was for many years horse editor of the Boston Globe, writing a weekly column titled “Hoof Prints.” Trott first worked on a local newspaper owned by his father, Lemuel Trott, but he then moved to Boston and began work with the Globe, becoming horse editor in 1896.  He also served as race secretary at many New England tracks as well as a judge at the leading meetings, including the Grand Circuit. According to his obituary, he was known as “the dean of harness horse writers in the country” and wrote so expertly about horses “in a way that won him the confidence and respect of owners and trainers everywhere.”13 He was an avid participant in iceboating.  As skipper on his own boat, he earned many trophies in contests held at the Mystic Lakes and other ice courses.

Maribel Vinson Owen, in addition to being a championship skater and coach, was the first female sportswriter at The New York Times. She also contributed to The Associated Press and Boston Globe, for which paper she covered the 1948 Olympics in St. Moritz.

George B. Underwood (1884-1943), a 1904 Summer Olympics medalist, became a sports writer in 1904, working for papers in New York. For ten years he was a sports editor for the Boston American and later was a news editor for the Boston Globe.


1. Excelsior [Edwin A. Wadleigh], The Middlesex Journal, Oct. 5, 1867.
2. Bruce Winchester Stone, History of Winchester, II:29.
3. Bruce Winchester Stone, History of Winchester, II:185.
4. H. Dudley Murphy letter to Henry Chapman, n.d. Baxter was the first secretary of the Massachusetts Metropolitan Park Commission. He and Charles Eliot were major forces in the development of the Metropolitan Park System of Greater Boston
5. Interview of Bob Walsh by Laura Reboul, July 22, 2010.
6. The Winchester Star, Nov. 7, 1919.
7. Interview of Addison Lane McGovern by Charlene Band, February 2, 2005.
8. Interview of Bob Walsh by Laura Reboul, July 22, 2010.
9. The $12,000 expended on the path was funded 50/50 by the town and state.
10. The Winchester Star, Feb. 25 and March 17, 1916
11. The Winchester Star, March 11, 1938.
12. The Winchester Star, July 19, 1946
13. The Winchester Star, August 26, 1949.