Highwood is a vibrant North Shore village just 25 miles north of downtown Chicago. Known for its historic charm, walkable streets, and engaged community, it attracts young professionals. Local shops, cultural venues, and annual events give Highwood a unique personality, blending small-town energy with North Shore sophistication.
Highwood offers a compact, walkable village with parks, restaurants, and cultural venues. Expect active streets, seasonal markets, and community events, all within reach of nearby Highland Park, Lake Forest, and Chicago.
Life in Highwood blends small-town charm with energy. Residents enjoy dining, boutique shopping, parks, and cultural events. Walking and biking are everyday activities that create a connected, social, and engaging community.
Explore Green Bay Road’s restaurants and shops, or attend Highwood Days and the summer Evening Gourmet Market. Activities also include playing or relaxing at Everts Park, and enjoying sports and programs at Don Skrinar Recreation Center.
Highwood began near the future Fort Sheridan after settlers arrived in 1846 and the railroad opened in 1851. Incorporated in 1887, the village grew with immigrant workers, especially Italian in the 1920s. Once famous for taverns and nightlife, it has since evolved into a lively, diverse North Shore community.
Highwood fosters a close-knit, active community with residents of all ages, from young professionals to retirees. Civic groups, clubs, and local initiatives, such as the Highwood Bocce Club, bring neighbors together. The village also hosts the Highwood Arts, Crafts & Drafts festival, featuring artists, live painting, kids’ activities, food, and drinks.
Highwood’s compact downtown along Green Bay Road offers cafés, restaurants, and boutique shops, including Deere Park American Brasserie. Residents can stroll the streets, enjoy local shopping, or relax at local parks, picnic areas, and open lawns. Don Skrinar Recreation Center hosts sports, classes, and community programs for all ages.
Nearby forest preserve trails offer walking, jogging, and biking. Seasonal events, such as Highwood Days and the summer Evening Gourmet Market, showcase local food, music, and culture. Visitors can also enjoy parks, public art, local shops, and eateries that highlight the village’s vibrant community.
Residents have access to several parks and green spaces, including Jensen Park and LaBagh Woods. The Chicago River runs through the neighborhood, offering scenic spots for walking, jogging, and relaxing.
Albany Park is one of the city’s most pedestrian-friendly neighborhoods. Grocery stores, restaurants, and shops are all within walking distance. Three CTA stations connect it to the rest of Chicago, and its proximity to major roadways makes commuting convenient.
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Highwood provides Everts Park and Highwood Ball Park, featuring playgrounds, sports fields, and open spaces. Nearby Fort Sheridan Forest Preserve trails offer walking, jogging, and biking for residents of all ages.
Highwood’s downtown offers a mix of restaurants and cafés along Green Bay Road, including Disotto and Da Local Boy Cafe. Boutique shopping is also available, with stores like Anna’s Mostly Mahogany. The village retains its small‑town charm, while nearby Highland Park and Lake Forest provide larger retail and specialty options.
Highwood attracts buyers seeking a walkable, historic village with parks, cultural events, and a strong community spirit. The village offers a mix of historic and modern homes, local shops, cafés, and recreational amenities. Residents enjoy quiet, small-town living while staying close to the North Shore and Chicago.
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If you’re considering making Highwood your home, the MG GROUP is here to help. Contact us to explore your options in this thriving Chicago neighborhood.
