Discover Highwood
Nestled on the prestigious North Shore of Chicago, Highwood, Illinois, offers a living experience that is as unique as it is desirable. A small city with a big heart, Highwood is a vibrant community that has managed to retain its distinctive character and charm amidst the affluence of its neighbors. Known for its rich history, diverse culture, and a culinary scene that rivals that of a much larger city, Highwood is a place where tradition and modernity blend seamlessly. The city’s welcoming atmosphere is palpable, with tree-lined streets, a bustling downtown, and a strong sense of community that makes residents feel right at home. It’s a place where neighbors know each other by name and where community events bring everyone together, creating a close-knit and friendly environment that is increasingly rare to find.
The history of Highwood is deeply intertwined with the arrival of Italian immigrants in the late 19th and early 20th centuries. Seeking a better life, these hardworking families were drawn to the area by the promise of jobs at the nearby Fort Sheridan and in the local businesses that catered to the soldiers. Their influence is still strongly felt today, from the many authentic Italian restaurants that line the streets to the strong family values that are at the core of the community. The city's name itself is a nod to its geographical location on a high bluff overlooking Lake Michigan. The Highwood Historical Society works to preserve and share the city's fascinating past, including its time as a dry town during Prohibition, a fact that only adds to its colorful history.
Families are drawn to Highwood for its excellent schools, which are part of the highly-regarded North Shore School District 112 and Township High School District 113. Younger students attend Oak Terrace School for kindergarten through fifth grade, a school known for its dedicated teachers and strong academic programs. From there, students move on to Northwood Junior High School for sixth through eighth grade, where they are prepared for the challenges of high school. Highland Park High School, which serves Highwood students for grades nine through twelve, is consistently ranked among the top high schools in the state and nation, offering a wide range of Advanced Placement courses and extracurricular activities. The school’s impressive academic achievements and commitment to student success make it a major draw for families considering a move to the area.

Highwood’s dining scene is a food lover’s paradise, with a concentration of exceptional restaurants that is surprising for a city of its size. The city’s Italian heritage is on full display at a number of authentic trattorias and pizzerias, where generations-old recipes are served with pride. But the culinary landscape is far from one-note. From fine dining establishments to casual eateries, there is something to satisfy every palate. The city is a destination for foodies from all over the North Shore, who come to enjoy everything from fresh seafood and prime steaks to creative cocktails and artisanal pastries. In the summer, the city’s weekly Evening Gourmet Market brings the community together for an evening of food, music, and fun, with dozens of vendors offering a taste of Highwood’s diverse culinary offerings.

When it comes to recreation, Highwood residents have a wealth of options to choose from. The city’s location on the shores of Lake Michigan provides easy access to beaches and water activities, while the nearby Fort Sheridan Forest Preserve offers miles of trails for hiking, biking, and cross-country skiing. The Don Skrinar Recreation Center is a hub of activity, with a gymnasium, fitness center, and a variety of programs for all ages. Everts Park, in the heart of downtown, is a popular spot for picnics and outdoor concerts. The Midwest Young Artists Conservatory and The Performer's School provide top-tier instruction in music and the performing arts, nurturing the next generation of artists and musicians.

The sense of community is strong in Highwood, with a calendar full of events and festivals that bring residents together throughout the year. Celebrate Highwood, a non-profit organization, is dedicated to promoting the city and its businesses through a series of popular events, including the Highwood Pumpkin Festival, which draws visitors from all over the Chicagoland area. The Highwood Historical Society plays an active role in preserving the city’s heritage, with a museum and a variety of educational programs. The Highwood Public Library is another important community institution, offering a wide range of resources and programs for all ages.
The real estate market in Highwood is as diverse as its residents, with a mix of housing styles that reflects the city’s history and evolution. The city’s older neighborhoods are filled with charming bungalows, Victorians, and other pre-war homes, many of which have been lovingly restored and updated. Newer developments offer a range of options, from single-family homes to townhouses and condominiums. The city’s close proximity to the lake and its convenient location on the Metra line make it a desirable place to live, and home values have been steadily increasing in recent years. Whether you are looking for a starter home or a luxury property, you are sure to find something to suit your taste and budget in Highwood.
In conclusion, Highwood, Illinois, is a city that has it all: a rich history, a vibrant culture, excellent schools, a thriving dining scene, and a strong sense of community. It is a place where you can enjoy the best of both worlds: the peace and quiet of suburban living with the energy and excitement of a much larger city. If you are looking for a place to call home on the North Shore, a place where you can put down roots and become part of a close-knit community, then look no further than Highwood. Come and discover for yourself what makes this city so special. You may just find that it is the perfect place to start your next chapter.
