By the time he died in Litchfield in 1872, Hubbard was one of the town’s largest landowners, amassing hundreds of acres of mostly wooded property and farmland along its eastern border. The wood frame farmhouse I purchased on Fern Avenue in Litchfield two summers ago — built on a 50-foot-wide patch of grass in 1920 — sits on 1.4 acres of that land today.

How I got here — a lifelong urban dweller who sought refuge in the town during the pandemic — underscores how a widening interest in learning about my home took me on a journey of discovery that revealed as much about Litchfield today as it did about the two centuries before I arrived.

That journey — through decades-old land deeds and census data, county tax records and library files — also connected me to the people, places and history of a pastoral town still dotted with family farms and where some residents travel across their properties on horseback.

And though its unspoiled scenery has long been a popular country retreat for affluent New Yorkers — with pockets of wealth and status — it has none of the pretentiousness found in other favored weekend locations.

“The town has always retained a genuine sense of community,” Lee Lyons told me as we walked across her horse farm just down the road from my house. This summer marks her 50th year of raising horses on the 100 rolling acres she operates at Lee’s Riding Stable. “We’ve seen some changes over the past few years, especially with more people moving here during covid, but the people of Litchfield still consider themselves neighbors.”

I bought my Litchfield home in the summer of 2020 as a weekend house to help escape Manhattan during the height of covid. Like many New Yorkers, I was cooped up and concerned about the post-pandemic future and grew tired of donning a mask each time I stepped outside of my Upper West Side apartment.

Set back from the road on a gentle slope, the small cottage is tucked beneath a grove of hickory and maple trees, some soaring more than 100 feet tall. Adding to its allure was its neighbor: It abuts Hauser Nature Preserve, a 110-acre swath of protected land in a town that safeguards much of its pristine landscape.

Listed at $189,000, the modest property with knotty-pine wood interiors and a cramped, country kitchen had already been on the market for months by the time I toured it. At just under 600 square feet, its size was likely off-putting to many second-home buyers with money to spend on something larger. (It was listed as the smallest home for sale in the town of Litchfield at the time of my closing.)

I eventually whittled the sale price down 40 percent from its asking price thanks, in part, to a charitable seller who owned and sold much larger properties nearby. Yet soon after I signed the deed, questions about the home began swirling inside my head.

Why were the narrow property lines on each side of the home marked by stone walls that ran the full length of the property? The home’s pitched roof was bifurcated; did that suggest the original structure was expanded in later years? And in a pocket of Litchfield surrounded by hundreds of acres of protected land, who built this tiny home in 1920 and how has it remained standing for 102 years?

“Once you start digging into Litchfield’s history, you’re not just going down one rabbit hole, you’re going down dozens,” said Cathy Fields, director of the Litchfield Historical Society. She and her colleague, archivist Linda Hocking, became important partners in helping me chart the town’s history during the time John Henry Hubbard roamed the land under my home. “Every stone you turn over here might reveal something new and interesting,” Fields said.

Land deeds showed the property has changed hands seven times since 1948 — proving I wasn’t the only buyer to see value in owning one of the thinnest spits of real estate within the town’s 57 square miles.

Sale prices for the property ranged from about $3,000 in 1953 to $18,000 in 1973. It reached $42,000 in 1981 and changed hands in 2004 for $200,000. Past owners were mostly couples from the New York City area who, like me, probably bought the home as a weekend retreat.

The man who sold me the home, Robert Kantor, also owned the 14-acre property next door and says he used my place as a guest cottage.

“It was always a favorite spot for my friends because it sat right next to the nature preserve,” said Kantor, a former fashion industry executive who later combined his background in fashion design with a passion for guitar collecting and began designing customized guitars for artists such as Lady Gaga, Richie Sambora and Lenny Kravitz.

“The place had great karma,” he said. “My friends always thought it was a relaxed little place to ease into.”

I reached my first dead end when I got to 1948. Some property deeds before that were handwritten, making it difficult to decipher which names were associated with my land or my neighbors. Adding to the challenge: Fern Avenue today was Fern Road until the 1960s and Chestnut Hill before 1968 when nearby Route 118 opened. And few homes before the 1970s had house numbers, said Sue Weston, who was raised on the 100 acres her family owned on Fern Road and remembers riding her bike along the street when it was actually lined with ferns.

“There were fewer houses on Fern Road back then,” said Weston, the lead interpreter at the Litchfield Historical Society. “The post office didn’t need a house number if your name was on the mail.” This meant I needed to incorporate county tax records in my research to help trace the owners of the property before 1948. It also forced me into library files and local history books to learn what I could about the names on the deeds.

Sifting through land records and census data of John Hubbard is when I learned that he not only owned my sliver of land dating back to the 1830s, but also the several hundred acres that surrounded it. It also revealed clues as to why my property lines were so narrow and lined with stone. As the Hubbards sold off land to the west and east of my home — keeping hundreds of acres that lay behind it — the family likely carved out my sliver of land as a road that led to their property. Tax records show they applied for an easement to allow that road to exist since the 1940s.

The back of my property is wooded and extends through the eastern edge of Hauser Nature Preserve next door. It also connects to Topsmead State Forest, a 510-acre swath of land that is a popular location for hiking and horseback riding.

Topsmead was formerly the summer residence of Edith Morton Chase, a scion of the Chase Brass and Copper Co., who received the first 16 acres of the land as a gift from her father in 1917. Land deeds for Tospmead revealed that in 1953 some 450 acres of land that once belonged to the Hubbards were eventually gifted to Chase to keep it free of development.

“It was not uncommon for wealthy landowners like John Hubbard to be gentleman farmers,” Vermilyea says. “But it’s also clear that Hubbard was conservation-minded like so many Litchfield residents at the time and he wanted to ensure that the land remained free of development.”

Discovering the history of my land still left open questions about the structure on the property.

The town’s building department didn’t keep complete records before the 1950s because it wasn’t required by law. And property deeds didn’t reveal details of structures on the land. Town historians I spoke with suggested the 1920 house with hardwood flooring and a working fireplace was likely constructed as a modest farmhouse.

Its simple floor plan and use of rustic materials popular for farmhouses of the period point to a home that was likely built out of necessity — not for leisure, says Steve Schappert, a Litchfield County real estate broker who spent decades building homes in the state before selling them.

That the home — bifurcated roof built on dirt instead of a concrete slab — suggests additions were added along the way, Schappert says. “It was likely a single-room dwelling with a fireplace in 1920,” he says. “The bath and kitchen were probably added later as the owners saw the potential for a year-round home.”

Going down the rabbit hole of discovery left me with some unanswered questions and slight disappointment, but the process — the people, places and history of my adopted weekend town — was nonetheless rewarding. A salient reminder that sometimes the journey really is the destination.

• Town hall: This is your first stop in establishing a chain of title of the home. The property card at the clerk or tax assessor’s office will reveal who has owned your home and what they paid for it. Most places now have this information online, but you may have to visit in person if you want to go back decades.
• Property deeds: Property deeds at the clerk’s office will show details such as the dwelling’s size and the property’s acreage and if that has changed over the years. Deeds should also lay out in more detail who has bought and sold the home dating back to its origin.
• The historical society: The local historical society often works with homeowners to research the histories of a home as well as the people who have owned it — especially if you uncover a noteworthy former owner.
• Paying a pro: In some cases, commissioning a professional to track down the history of your house could yield results. But it can be pricey — in some cases, setting you back a few thousand dollars. Those costs could sting even more if the results aren’t all that glamorous.

Investigating the history of your home

can be an exciting and rewarding endeavor.

By Steve Schappert

Here are some steps you can take to uncover information about the history of your home:

1. Start with your own records: Begin by gathering any documentation you have relating to the property. This may include purchase agreements, title deeds, or any previous ownership records. These documents can provide clues and references for further research.
2. Visit local historical societies or archives: Local historical societies or archives often have records and documents related to properties within their region. Visit or contact these organizations to inquire about any information they may have on your home. They might have old maps, photographs, newspaper clippings, or other relevant materials.
3. Search public records: Public records can provide valuable information about your home’s history. Visit the local town hall, courthouse or county recorder’s office to access property records, including previous owners, transfers, and other legal documents. You may also find tax assessment records that can help you track the property’s history.
4. Consult old maps: Historical maps can provide insights into the development and changes that have taken place in your area over time. Check with local libraries, historical societies, or online map archives to find maps that show your property. By comparing different maps from different periods, you can see how the land and structures have evolved.
5. Research newspapers and local publications: Local newspapers and publications often contain articles, advertisements, or classifieds related to property sales, renovations, or significant events in the area. Visit local libraries or online newspaper archives to search for mentions of your home or previous owners.
6. Talk to long-time residents: Reach out to long-time residents of your neighborhood or people who have lived in the area for a significant period. They may have firsthand knowledge, stories, or anecdotes about your home or its previous occupants. Their recollections can provide valuable insights into the history of the property.
7. Utilize online resources: Various online resources can assist you in investigating the history of your home. Websites like ancestry.com, familysearch.org, or city/county historical websites may provide access to census data, genealogical records, or local history databases. You can also search online directories, real estate websites, or historical property databases for information on previous owners.
8. Hire a professional researcher: If you’re having difficulty finding information or want a more comprehensive investigation, you can consider hiring a professional researcher or historian specializing in property history. They have expertise in conducting in-depth research and may have access to resources not readily available to the public.

Remember, investigating the history of your home can be a gradual process, requiring persistence and patience. Each piece of information you uncover will contribute to a clearer picture of your home’s past, adding to its unique story.