Fairfield County

Overlook Mansion // 1882

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Raised in an intellectual home of his widowed father, William Allen Jenner (1844-1915) graduated from Middlebury College as the youngest in his class with highest honors. He would go on to graduate from Columbia Law School and be admitted to the New York Bar in 1867, becoming a partner in a prestigious New York City law firm. Outside of practicing law, William Jenner studied and authored textbooks on the Latin language and was an avid horticulturalist. His landscape architecture passion was fulfilled when he purchased a large house lot on High Ridge Road in Ridgefield Connecticut, and built this home in 1882, named “Overlook”, where he and his family would spend their summers outside of the city. Mr. Jenner and his wife, Josephine Curtis Jenner, raised three daughters between New York and Ridgefield. One of their daughters, Anna, would marry Sterling Foote, a New York City cotton broker. The Foote’s would inherit Overlook and spend their summers here until their death. The Queen Anne/Shingle style mansion showcases the shift of Ridgefield from sleepy farming town to summer destination for wealthy New York residents, a trend which continues to this day.

“Good Cheer Estate” // c.1820

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Originally built as a Federal period farmhouse, this gorgeous estate is the epitome of what happened to Ridgefield… city money! By the end of the 19th century, wealthy New Yorkers were flocking to small towns every summer for clean air, rest, and relaxation. Ridgefield, Connecticut became an obvious option for its close proximity to New York and bucolic setting of farmlands bounded by old stone and rolling hills. As a result, wealthy summer residents purchased older estates and either demolished or renovated the homes there. Aaron Lockwood Northrop was raised in Ridgefield and was educated in its private schools before moving to New York as a young man, being awarded an apprenticeship as a dentist. Dr. Northrop went on to establish a prominent dental practice and would serve as President of the American Dental Association. As a wealthy adult, he acquired a circa 1820 house on this lot and renovated it, doubling its size and giving the residence its current Victorian flair. The summer house was affectionately named “Good Cheer”. Aaron died unexpectedly in 1908 while overseas in Paris, France. His widow, Caroline, resided at Good Cheer until her own death in 1927.

Maynard Estate // 1901

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One of the largest summer estates in Ridgefield is this Neoclassical residence on Peaceable Street, which was built in 1901 for Effingham Maynard and his wife Helen. Maynard was a partner in Clark & Maynard, a New York publishing house. Local lore states that the Maynard Family hired New York architect Stanford White, to design this property, but no definitive proof could be located to substantiate that rumor. The Olmsted Brothers landscape architecture firm designed the grounds which were elaborate with gardens and outbuildings. The two unmarried Maynard daughters, Mary and Helen spent their summers here every year until their deaths in the 1950s.

Cheesman Mansion // 1887

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Timothy Matlack Cheesman was born in New York City in 1824, a son of physician, John Cummins Cheesman. Following in the footsteps of his father, he graduated in 1859 from the College of Physicians and Surgeons, now known as Columbia University Vagelos College of Physicians and Surgeons. Timothy served as Surgeon in the 7th Regiment NY National Guard in 1853 and upon the start of the Civil War, he mustered into US service April of 1861 as a Surgeon. In the late 1880s, like many other wealthy New Yorkers, Dr. Cheesman and his wife, Maria, decided to build a country home in Ridgefield, Connecticut. They chose nearly 30 acres on the east side of East Ridge, an area that was being touted as “Prospect Ridge” for its view. Dr. Cheesman was ill with Bright’s disease and and may have been seeking the clean air of the country climate to help his health or at least as a place to rest. Sadly, he died one year later in 1888, and did not get to fully enjoy his country retreat. He was 63 years old. His widow Maria continued to use Matlack (the house’s name) until her death in 1903. In 1922, the estate was acquired by the Holy Ghost Fathers, who set up a school for new members of the order who would get their initial training to be priests or brothers there. Declining membership and costs required them to sell the campus, which was acquired by the Town of Ridgefield in 1971. Matlack is now the centerpiece of a large housing complex for the elderly in town and is managed by the local housing authority.

Lewis June House // 1865

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The Lewis June House sits on North Salem Road in northern Ridgefield, Connecticut, and is one of the finest Second Empire style homes in this part of the state. The c.1865 home was built for Lewis June (1824-1888), who was in the circus business, and it replaced an earlier home on the site that burned. Lewis June was a partner in the June, Titus and Angevine & Co. Circus that as early as 1842 toured 85 towns in six states. The circus wintered in Ridgefield. Past owners have since found many horseshoes, largely of small horses, on the property, suggesting that June kept the circus’ horses and ponies on this property. The home has been preserved thoughtfully and was listed on the National Register of Historic Places in 1984.

Branchville Railroad Tenement // c.1853

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The Branchville Railroad Tenement in Ridgefield, Connecticut was built in three phases between around 1853 and 1905 and is one of the towns significant vernacular landmarks. Its earliest incarnation was as a storage facility for the railroad station, to which two stories of residences were added to houses workers on the railroad. Following completion of the railroad, the building was converted into a hotel in 1880, at which time the two-story porch was built and the interior was redecorated. This was apparently an unsuccessful venture, and in 1905 it was converted to a saloon and multifamily residence. Today, the old railroad tenement is home to a small business with housing above.

Benedict House // c.1740

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The Benedict House in Ridgefield, Connecticut is a stunning Colonial-era cottage that was once the home of a cobbler, who had his shop on the property. The Benedict family, headed by James Benedict, Sr., were original proprietor settlers of Ridgefield. This house and shop have been attributed to James’ son James Benedict (1685-1762), who owned the land and was a shoemaker and deacon of the Congregational Church. Ensign Benedict was also a fence viewer, a term new to me. Fence viewers had power to make and enforce rulings regarding escaped or trespassing livestock, the location of fences, and, above all, maintenance of fences. With fences so crucial to keeping livestock where it belonged, loose boards and rotting posts were big concerns. The fence viewer could even compel a property owner to pay for needed maintenance or repair conducted by a neighbor if he or she failed to keep up their fence properly. The property left Benedict family ownership in 1848, and it was later extensively restored by renowned architect Cass Gilbert, who bought the property in 1920. Cass Gilbert also restored a few other Colonial-era houses in town. It was later the home of Robert and Mildred Wohlforth, both writers of note and six-decade residents of Ridgefield.

David Scott House // 1714

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One of the oldest extant houses in Ridgefield, Connecticut is this charmer, which was moved not once, but twice! The house was built for David Scott (1678-1760), an Irish-born resident of the town, who purchased one of the town’s original Main Street house lots which sat undeveloped. Scott had abandoned his wife, Mary in Ireland, and settled in Ridgefield, entering into a new relationship with Elizabeth St. John. A woman scorned, Mary unexpectedly arrived in America and filed suit against her husband, citing Elizabeth as the “pretended wife of David Scott.” A judge awarded Mary three acres of her husband’s land. David Scott and his second wife lived at this 1714 house until they moved in 1740. His property (which included two enslaved Africans) was sold to Vivus Dauchy, a Frenchman. In the 1920s, as the Scott House section of Main Street commercialized, the owners relocated this house to Catoonah Street, building a commercial block in the former location. After numerous other owners, the most recent owner, The Ridgefield Preservation Trust (now the Ridgefield Historical Society) put it to use as a new historical society headquarters, after saving the Colonial-era home from demolition for stores and a parking lot! It was relocated to its current site and has been meticulously restored.

Ridgefield Train Depot // 1870

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In 1870, the Ridgefield Branch branch line of the Danbury and Norwalk Railroad and later the New York, New Haven and Hartford Railroad was built connecting the sleepy village of Ridgefield to Branchville train station via the main line. The line was an early risk, built to offer service to the wealthy New Yorkers who began arriving to spend their summers in Ridgefield. Many of these “summer people” had their own private railroad cars, with chauffeurs meeting them as they arrived, driving horse and buggies to bring them and their luggage to their estates located throughout the town. As travel shifted to personal automobile, ridership dropped in the early 20th century, and the branch was replaced by bus service in 1925. Freight service was scarce, and lasted longer, to 1964. The depot was sold to the Ridgefield Supply Company, who used the 1870 building as storage for decades until it was disassembled, moved and rebuilt by the Ridgefield Supply Company in 2015, as part of their expansion. The historic station today provides an important link to Ridgefield’s past.

Ridgefield Public Library // 1901

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The Ridgefield Public Library is an intriguing Beaux Arts style building from the turn of the 20th century. Built in 1901, the brick structure replaced the Smith Tavern, a 1798 frame structure built by Amos Smith right on Main Street. In 1900 the Smith Family sold the property to James N. Morris who had this library built in memory of his wife, Elizabeth, donating it to the town. Architect Raleigh G. Gildersleeve is credited with the design which is comprised of a one-story building constructed of brick with cast stone trim details and ironwork at the door. The library was given later additions, which are recessive in location and detailing to let the original building shine, as it should!