The Roots of Highwood Farms
Nestled in the gentle hills of Thomaston, Connecticut, the Highwood Farms neighborhood has long been cherished for its blend of storied past and vibrant community spirit. Just west of Main Street and bordered by the winding curves of High Street and Walnut Hill Road, this enclave today embodies both old-world charm and the quiet joys of small-town living.
The origins of Highwood Farms date back to the late 19th and early 20th centuries, a period when Thomaston's population was burgeoning, thanks to the prosperity brought by the Plymouth Hollow clock-making industry. Originally, much of what is now Highwood Farms was open farmland, part of a patchwork of agricultural properties that helped sustain the growing town. The area’s rich soil and wooded knolls gave rise to its name: "Highwood" refers to the stately, mature trees that once crowned the ridgelines, and "Farms" to its primary use before suburban development transformed the landscape.
Naming and Early Growth
The neighborhood first began to take shape in the 1920s as returning World War I veterans and their families sought to settle on the edges of Thomaston's bustling center. At the time, local records show, the land was purchased from the Barlow and Peterson families, whose dairy and apple farms supplied fresh goods to the town’s general stores. Deeds from 1923 reference "The Highwood Tract," marking the earliest use of the name.
It was during this period that main arteries like Highwood Avenue and Farms Road were platted out, offering generous lots and gentle slopes—a welcome departure from the tight, clustered homes of Thomaston's downtown. Early advertisements in the Thomaston Express extolled the "fresh air and scenic vistas" available in Highwood Farms, attracting young families and retirees alike.
Key Historical Milestones
- 1928: Highwood Farms Community Hall Built
One of the neighborhood’s key gathering places, the Highwood Farms Community Hall (still standing near the corner of Highwood Ave and Cedar Lane), provided a venue for dances, suppers, and town meetings for over 50 years. Its shingled facade and wooden porch remain a nostalgic nod to days gone by.
- 1947: Greenridge Park Established
The donation of three acres by the Abbott family, whose land at the top of Walnut Hill was famed for springtime wildflowers, led to the creation of Greenridge Park. Today, its playground and tree-shaded benches serve as the heart of neighborhood gatherings.
- 1964: First Highwood Carnival
Organized by the residents’ association, the annual summer carnival began as a small picnic and quickly blossomed into one of Thomaston's most beloved local traditions—complete with games, food stalls, and community spirit.
Notable Landmarks and Buildings
Walking through Highwood Farms, visitors and residents are greeted by a mix of historic homes and welcoming public spaces:
- Highwood Farms Community Hall
As mentioned, this hall has seen decades of community celebrations, weddings, and even served as a makeshift schoolhouse during the icy winter of 1936 when pipes burst in the downtown primary school.
- St. Anne’s Chapel
Built in 1932 with locally quarried stone, St. Anne’s is an enduring symbol of the area’s faith traditions and neighborly values. Its annual Harvest Festival draws visitors from throughout Litchfield County.
- Greenridge Park
Tucked between Farms Road and Pine Grove Avenue, Greenridge Park’s open meadows and shaded walking paths offer a tranquil escape and a natural playground for young and old alike.
Streets that Tell a Story
One of the most endearing aspects of Highwood Farms is its mosaic of storied streets. Highwood Avenue, once a dirt lane lined with maples, now boasts a series of well-maintained Colonial and Cape Cod homes, many lovingly restored by second- and third-generation families. Cedar Lane, named for the fragrant old cedar grove near its north end, still hosts original stone walls built by the neighborhood’s first farming families.
Several streets were named in tribute to Thomaston’s early civic leaders: Abbott Lane honors Edward Abbott, whose generosity helped establish Greenridge Park; Barlow Court commemorates the Barlow family’s early contribution to the neighborhood’s agricultural roots.
Evolution Through the Decades
The years following World War II saw significant change. As demand for suburban living increased, new homes were constructed on previously unused lots, though care was taken to preserve mature trees and community green spaces. The 1970s brought a surge of young families, and the opening of Highwood Elementary School on Willow Road further solidified the neighborhood’s reputation as an ideal place to raise children.
In recent years, Highwood Farms has continued to evolve, blending the historic with the contemporary. You’ll find lovingly maintained bungalows side-by-side with thoughtful new builds designed to complement the area’s character. Residents take pride in community-led initiatives, from neighborhood clean-up days to the restoration of the historic Highwood Farms sign near the neighborhood entrance on Walnut Hill Road.
The Spirit of Community
What truly sets Highwood Farms apart, longtime residents agree, is the spirit of community that endures through generations. Neighbors swap pies and stories on front porches, pitch in for block parties, and lend helping hands when storms pass through. The annual Highwood Carnival and summer “Concerts in the Park” series at Greenridge Park are cherished rituals, drawing families, friends, and newcomers together year after year.
Preserving the Past, Embracing the Future
As Thomaston continues to change and grow, Highwood Farms remains a beacon of what makes small-town living so rewarding. Its leafy streets, historic gathering spots, and welcoming neighbors ensure that the neighborhood’s legacy of warmth and hospitality lives on—promising a bright future rooted in a remarkable past.