Criteria A

Farming Community
Weston was predominantly a farming community from its earliest years of settlement through the 19th century. The land in the Glen Road Historic District was originally part of a 150-acre grant allotted to Watertown resident William Jennison (also spelled Jenison) in 1642, when the area of Watertown known as The Farms (now Weston) was divided into 92 farms. At that time the land was used primarily for grazing cattle.

Nathaniel Jennison House
In 1732, William’s 22-year-old collateral descendant, Nathaniel Jennison, inherited part of the land and built the first house in the Glen Road Historic District. The Nathaniel Jennison House at 266 Glen Road (1732, Map #17, MHC 306, Photo 5) was originally located across the street from its present site. Jennison’s first 3 children were born in Watertown, but the third child was baptized in Weston in 1732, indicating that the house was built that year. Jennings farmed almost 40 acres.

Pot-Ash House
Later deeds also mention a “Pot-Ash House” on the property. Potash, an alkali used in the manufacture of soap and glass, was made from burning hard woods to a fine ash and was an important commodity in the colonies.

Pratt/Wyman House
The Pratt/Wyman House at 317 Glen Road was built about 1812 and updated in the mid-19th century with an Italianate hood and double doors.
History of Pratt/Wyman
By the later 18th century, part of the Jennison land had passed into the hands of the Pratt family. The 1794 map of Weston shows a house at the northwest corner of Oak Street and Glen Road belonging to Paul Pratt. About 1812, he built a fine Federal house at the northeast corner. According to tradition, Pratt moved the original house and attached it to the back of his new house, the Pratt/Wyman House at 317 Glen Road (ca. 1812 with earlier ell, Map #33, MHC 220, Photo 4). Farmer Daniel Wyman bought the 72-acre property in 1850 and updated the house with an Italianate hood and door. Wyman’s descendants operate a farm here into the 20th century, raising a variety of crops for family consumption and strawberries as a cash crop. They owned the house until recent years.
The Pratt/Wyman House at 317 Glen Road (1812); updated in the mid-19th century
In 1817, Josiah Seaverns sold 114 acres of former Jennison land to Joseph Winship, who was also a farmer. In 1826, Winship sold the farm to Levi Jennings, who left it on his death in 1870 to the five children of his son, Levi, Jr. One of the five, Edward, later purchased the shares of most of his siblings, and in 1900 owned 149 acres. Edward and his wife Ella had five sons and no daughters.

Glen Farm Operations
During the last quarter of the 19th century, Edward developed an extensive dairy operation at “Glen Farm.” The following information appeared in the 1902 Wellesley publication Our Town:
Milk delivery truck in front of the Edward Jennings Barn, early 20th c.
While he (Edward Jennings) started with four cans a day, he now has three wagons on the road. He has between 100 and 125 cows and employs over 20 men, with an equal number of horses. It requires about 75 acres of green fodder for the cattle, a large proportion of which is stored in two silos, each with the capacity of many hundred tons. Two years ago, Mr. Jennings was burned out, but the great barn shown at the left of the larger illustration was soon built and dairy machinery of the latest pattern installed. The apparatus for filling a large number of bottles at a time; the separator; the refrigerator, and the other appliances of modern dairying form an interesting exhibit, well worth a special visit to see. Mr. Jennings’ wagons go as far as Brighton, and one of his special contracts is to furnish the entire supply of milk for Lasell Seminary at Auburndale.
According to tax records, the peak of operation was 1903, when Edward was taxed for 112 cows. Photographs taken about 1902 show two large barn complexes. The farm also included an apple orchard.

Glen House Hotel
The Glen House Hotel on Glen Road was operated by Willard Jennings in the late 19th and early 20th century.
Willard Jennings
While Edward was developing his dairy farm, his brother Willard was expanding his business in different directions. Willard was also a farmer, but he had considerably less land than his brother and utilized it to raise vegetables and fancy raspberries for the Boston market. Market gardening and dairying were the two agricultural specialties where Weston farmers in the post-Civil War era could effectively compete. About 1875, Willard built the Mansard-style Willard Jennings House (later Glen House Hotel) at 245 Glen Road (ca.1875/1931, Map #7, MHC 373).
The Glen House Hotel was operated by Willard Jennings in the late 19th and early 20th century
Summer Boarders & Train Lines
Some time before the turn of the century, Willard began to take in summer boarders - fairly common way for farmers to supplement their income. By then, Weston had become a popular destination for Boston residents seeking to escape the summer heat. This popularity was due in part to the town’s location along three different train lines. The southernmost line, originally the Boston and Worcester, was constructed in the 1830s and, in 1867, merged with the Western Railroad to form the Boston & Albany. Although there was no station in Weston, the Wellesley Farms train station was located less than a mile from Willard’s house.

Willard kept adding to his original residence. The expanding summer resort, called Glen House or the Glen House Hotel, reportedly included forty guest rooms and a ballroom. At the turn of the century, to promote ridership, the railroad put out a brochure called “Summer Homes” with descriptions and photographs of resort hotels along the line, including Glen House. The photograph shows the original house and large 2 1/2 story gambrel-roofed wing. The hotel is listed in directories from 1911 to the early 1920’s.

Cottages on Glen Road
Willard built 5 nearby cottages, of which four remain at 233, 235, 241 and 247 Glen Road (early 20th century, Map #1,2,3,9, MHC 486, 487, 488, 490). These were used at various times for guests, staff, and family members.

An advertisement for “Glen House and Cottages” describes the establishment as follows:
  • High location near station, in Wellesley Farms. The beautiful section often called the ‘Lenox of the East.’ Our neighborhood is composed of a select class who come here to spend their summers. Business men find the place convenient to Boston, as well as a healthy location. Automobile parties accommodated. Tennis, billiards, auto service, garage, etc.
Children visiting the resort could play on the farm while their fathers commuted quickly into Boston by train from the nearby Wellesley Farms station. Families returned each year with their chauffeurs and personal maids. Isabel Jennings did the cooking and Willard Jennings maintained flower beds which furnished fresh flowers in the dining room. The last listing for Glen House is in the 1921-22 directory. The next directory, 1926, does not include the hotel, suggesting that it had closed by that date. According to the present owner, two fires, the second in 1931, destroyed the wing and third floor of the original house.

Continuing Operations
Edward’s Glen Farm reached its peak of operation in 1903, the year his largest barn was destroyed in a December fire. He continued dairying on a smaller scale, and, beginning about 1916, developed a chicken and egg business. The decision of the Jennings and Wyman/McNutt families to hang onto their land and try to adapt to changing social and economic conditions contrasted with the decision of other Weston farmers to sell out to wealthy Bostonians who purchased farmland for country estates. By the early 20th century there were 4 such estates in the immediate vicinity of the Glen Road Historic District.

House Construction

Although Edward managed, with difficulty, to keep the farm going, he was not a good businessman. To supplement his farm income, he periodically constructed houses fronting on Glen Road to sell or rent. His son Warren built most of these houses, which were attractive to middle class residents who liked the rural atmosphere and proximity to the Wellesley Farms train station.
Jennings Houses
The first of the Jennings-built houses, constructed in 1913 at 260 Glen Road (Map #14, MHC 510, Photo 3), was built for the second son of Edward Jennings, Clifton Victor (b.1879), who became a stockbroker. Two years later, Clifton built an almost identical house next door at 262 Glen Road (Map #15, MHC 509) and moved there. Two more houses were built in the 1910s, including the house for insurance agent Charles Noyes at 246 Glen Road (1917, Map #8, MHC 513, Photo 1).
Mr. and Mrs. Edward Jennings and their son Levi
Division of Jennison House
The pace of building increased in the 1920s. In 1924, the family homestead (the original Jennison House) was divided into two sections, and the 18th century (west) portion moved across the street to its present location at 266 Glen Road (Map #17, MHC 306, Photo 5). It was sold to Paul K. Thomas, who worked in real estate and as a stockbroker in Boston. The former east wing was moved back from Glen Road and slightly to the east and remodeled into a single family house (now 259 Glen Road, Map #13, MHC 492), occupied by Warren Jennings, who worked with his father on the farm when he was not building houses.
276 Glen Road (1923)
Sons of Edward Jennings
Edward’s eldest son, Levi Brown Jennings (b.1878), who became an interior decorator, lived in the Jennings-built house at 277 Glen Road (1923, Map #21, MHC 495). A third son, Charles Dudley (b.1885) lived in a house at 287 Glen Road which was destroyed by fire in 1958. Charles was in charge of milk deliveries and collections. He and his wife boarded as many as four drivers who delivered milk to Newton and Wellesley in horse-drawn vehicles, beginning their routes at midnight. During the later part of his life, Edward Jennings lived in a house he built at 270 Glen Road (1924, Map #18, MHC 508, Photo 5). Large hen houses were located at the rear of that property.

Houses in the District
The Jennings family built approximately 18 houses in the district, many of which share the same plan. In some cases, the completed houses were sold to businessmen and middle-level managers. Number 276 Glen Road was sold to Charles Hutchinson, a bond salesman; #281 to Joseph G. Hallett, who is variously listed as a manufacturer, manager, and proprietor in dry goods; #291 to merchant William I Wood; #294 to manager Thomas McCoy; and #301 to Harold Abbott, also listed in directories as a manager. In other cases the Jennings retained ownership and rented the houses. In 1930, Edward’s wife Ella is listed in town tax records as owning eight houses, including houses belonging to her sons Warren and Charles. In addition, she and Edward owned their own house, and their sons Clifton and Levi and daughter-in-law Mildred owned their own houses, making a total of 12 houses owned by the family at the beginning of the Depression. Most of the rented properties were sold by the bank in the early 1940s for non-payment of mortgage loans.

Glen Farm Water Company
Edward developed a small water system that eventually serviced 32 houses in the neighborhood. Operating under the name “Glen Farm Water Company,”this system apparently included a well, two windmills, and a large wooden water tank on the west side of Glen House Way. At one point, when the Jennings property was in foreclosure proceedings, this water supply was cut off and arrangements were made to tie the neighborhood into the Wellesley water system.

Financial Difficulties
Edward Jennings got into serious financial difficulties during the Depression, when he was in his 80s. In 1932, about 80 acres of Jennings land was acquired by the Town of Weston for nonpayment of taxes. His cows became infected with tuberculosis in the late 1930s and had to be destroyed. The chicken houses were damaged in the 1938 hurricane and many of the chickens lost.

311 Glen Road
While most of the houses in the district were built by the Jennings family, 311 Glen Road (1923, Map #32, MHC 502) is an exception. It was built for Frederick Young after he left his job as caretaker/manager of the Dean Estate.

From Farm Town to Suburb
After World War II, Weston completed the transition from farm town to suburb. Just outside the district, former Jennings farm land was developed as a baseball field. The various Jennings barns and outbuildings within and just outside the district were gone by the 1950s. A few post-war houses were built on remaining lots.

Other Events & Remodeling
Since then, the Glen Road Historic District has remained largely unchanged. Charles Jennings’s house at 287 Glen Road burned in 1958 and was replaced. Just outside the district, at the corner of Glen Road and Oak Street, the land formerly belonging to the Wyman/McNutt family is being developed with luxurious mansions on lots of 60,000 square feet and larger. Some houses within the district have been expanded or remodeled, in one case, at 262 Glen Road (1915, MHC 509, Map #15), with little sensitivity to the original design. Although the alterations are unfortunate, the house continues to contribute to the district because of similarities in scale, setback and massing. Because of the high cost of real estate in Weston at the turn of the 21st century, preservation will depend on sensitive remodelings which expand the size of the houses and provide additional amenities without destroying their individual charm and the character of the district as a whole.