Highwood

Living in Highwood: The North Shore’s Culinary Capital

I’ll be honest with you, whenever I’m showing homes up on the North Shore and we hit Highwood, I tell my clients to roll the windows down. You can literally smell the garlic and wood-fired crusts in the air. People ask me all the time, "Chris, why would I move to a tiny town like Highwood when I could have a massive yard in the neighboring burbs?" And I always tell them the same thing: because in Highwood, your "backyard" is one of the best dining scenes in the country. It’s that rare place where the energy of a city food crawl meets the warmth of a neighborhood where the restaurant owners actually know your kids' names. Buying here isn't just about the four walls; it’s about having a permanent seat at the table in the North Shore’s liveliest room.

The Ethos: Epicurean Spirit and Urban Energy

Highwood is the North Shore’s non-conformist. It is a community that thrives on connection, celebration, and a shared love for the finer things in life—specifically food and drink.

• The "Dining Room" of the North Shore: Highwood has one of the highest concentrations of restaurants per capita in the country. It is a culinary destination that draws people from across the Midwest, yet for residents, these world-class tables are simply "the local spot."

• A European Vibe: The town’s history is deeply rooted in Italian heritage, which manifests today in its walkable downtown, vibrant street life, and a culture that prioritizes gathering in the public square.

• The Festival Capital: Highwood doesn't just host events; it throws city-wide celebrations. From the world-famous Pumpkin Fest to the high-spirited Bloody Mary Fest, the village is a permanent stage for community joy.

A Day in the Life: The Highwood Rhythm

The Morning: The day begins in a downtown that is surprisingly quiet before the evening rush. You’re likely grabbing an artisanal pastry or a strong espresso at a local cafe before heading to the Highwood Metra station—a central hub that makes the 45-minute commute to the Loop or the 15-minute hop to Evanston effortless.

The Afternoon: Leisure in Highwood is about proximity. You might be exploring Everts Park, the town’s green heart, or taking a short walk to the lakefront at nearby Rosewood Beach. On Wednesdays in the summer, the Highwood Evening Gourmet Market transforms the park into a "Ravinia-like" experience with live music and over 60 gourmet vendors.

The Evening: This is when Highwood truly comes alive.

• Culinary Excellence: You might be having a sophisticated seafood dinner at Froggy’s French Cafe, an institution of the North Shore, or enjoying the modern, high-concept dishes at Disotto.

• Casual Luxury: For a more relaxed evening, residents frequent Bent Fork Bakery for legendary desserts or grab craft cocktails at a boutique bar along Sheridan Road.

The Real Estate Market: Walkable Sophistication

Real estate in Highwood is highly competitive, appealing to those who favor walkability and urban-style luxury over sprawling acre estates.

• Modern Luxury Developments: Recent years have seen a surge in high-end condos and luxury townhomes, designed for professionals who want a "lock-and-leave" lifestyle in the heart of a vibrant district.

• Character-Filled Homes: The side streets are home to beautifully renovated bungalows and historic Victorian-era houses that offer charm and character within a short walk of the downtown center.

Education: The Best of Both Worlds

Highwood residents benefit from an educational landscape that combines small-town attention with big-district resources.

• Oak Terrace Elementary: A landmark institution with a "Prairie-style" look, offering a tight-knit community feel for the village's youngest students.

• Highland Park High School: For secondary education, Highwood students attend HPHS, sharing in the same elite academic, athletic, and artistic legacy as their neighbors in Highland Park.

Highwood Quick Q&A

Is it too loud? While the festivals bring energy, the residential pockets just one block off the main drag are remarkably peaceful retreats.

What is "Garlic Fest"? A summer tradition dedicated to all things garlic—including garlic ice cream. It perfectly encapsulates Highwood's quirky, food-obsessed personality.

Is it walkable? Completely. It is one of the few North Shore towns where you can genuinely live without a car, with everything from the train to 40+ restaurants within a 10-minute walk.