A Neighborhood Steeped in History
Nestled at the northern edge of Highland Park, Highwood Terrace stands as one of the city’s most enduring and distinctive neighborhoods. Bordered by St. Johns Avenue to the west and just steps from vibrant Highwood to the north, Highwood Terrace enjoys a unique position at the crossroads of Highland Park’s history, culture, and daily life. As you stroll down its tree-lined streets—Labadie Avenue, Oakwood Avenue, and Summit Avenue among them—stories of old are never far from reach.
Origins: Foundation and Naming
Highwood Terrace traces its origins back to the early 1900s, at a time when Highland Park itself was transforming from a rural retreat into a bustling North Shore community. The neighborhood’s name is a testament to its perch above the surrounding area—a subtle rise that once offered vistas of woodlands and Lake Michigan in the distance. Early developers recognized the allure of these heights, branding the area "Highwood Terrace" after both its elevation and proximity to the adjacent city of Highwood.
The community quickly became a haven for families seeking a tranquil setting within easy reach of the North Shore rail line. The legacy of those early settlers still shapes the neighborhood today, with many original homes—quaint bungalows and stately brick houses—gracing the streets.
Key Historical Milestones
- 1910s–1920s: The Suburban Boom
- Highwood Terrace experienced its initial growth as the Chicago and North Western Railway brought commuters and businesses northward.
- The area’s early architecture reflected prevailing tastes: American Foursquares and Colonial Revivals with wide front porches.
- Post WWII: Expansion and Community Building
- Like much of Highland Park, Highwood Terrace swelled with new residents in the 1940s and '50s.
- Young families flocked to tidy streets like Hazel Avenue, drawn by the promise of good schools and a tight-knit environment.
- Community organizations took root, including local garden clubs and civic associations.
- Late 20th Century: Preservation and Modernization
- The 1970s and '80s saw a renewed appreciation for the area’s historic homes.
- Residents banded together to preserve the neighborhood's character, even as modern amenities were added.
Notable Landmarks and Institutions
Highwood Terrace may be a quiet residential enclave, but it boasts a host of charming landmarks that give it a sense of place:
- Highwood Park
The neighborhood’s green heart, Highwood Park, lies just east of Labadie Avenue. With its shady trees, playground, and open field, it’s a gathering place for block parties and seasonal celebrations.
- Historic Residences
- Several homes along Summit Avenue and Oakwood Avenue date back nearly a century and display original brickwork and distinctive gables.
- Temple Jeremiah & Community Spaces
- Not far from the neighborhood, Temple Jeremiah serves as a social and spiritual home for many residents, reinforcing the mix of faiths and backgrounds that define Highwood Terrace.
Evolution Across the Decades
The story of Highwood Terrace is one of evolution and resilience, where change has occurred thoughtfully and organically.
- Architectural Changes
- While the architectural landscape has diversified, careful renovations honor classic designs. Enlarged kitchens, finished basements, and eco-friendly features now blend with period details.
- Demographic Shifts
- Newcomers from Chicago and beyond have brought fresh energy without displacing the neighborhood’s rooted families. The result is a welcoming blend of young professionals, retirees, and multigenerational households.
- Walkability and Connection
- The creation of several pedestrian-friendly pathways in the 2000s has made it easier for neighbors to connect and for children to safely reach nearby schools such as Oak Terrace Elementary.
- Community Traditions
- Seasonal block parties and the annual neighborhood yard sale are beloved traditions that speak to residents’ enduring camaraderie.
Why Highwood Terrace Remains Special
Ask any long-timer what sets Highwood Terrace apart, and the answer is likely to be the enduring sense of community. Whether it’s an impromptu gathering at Highwood Park, the sight of neighbors chatting on front porches, or the way old and new residents alike pitch in to maintain the area’s beauty, the neighborhood’s heritage is palpable.
There’s also an immense pride in the physical environment. Tree canopies arch over streets in the summer, showering everything in green. The crisp autumn air brings families out to walk their dogs or join in Halloween festivities. And in winter, it’s not uncommon to see block after block shoveling together after a big snow.
A Legacy for the Future
Highwood Terrace is more than a charming enclave—it’s a piece of Highland Park history that continues to welcome new stories. The stewardship of its residents ensures that the neighborhood’s distinctive identity, architectural legacy, and grounded warmth will persist for generations to come.
Whether you are visiting, considering a move, or lucky enough to call it home, Highwood Terrace invites you to savor the deep roots, enduring beauty, and neighborly spirit that make it a beloved part of Highland Park’s living heritage.