4 Things to Do in Your First Week in Winnetka

Located just a short drive from the northern border of Chicago, Winnetka is one of Illinois’s best-kept secrets. The small town sits right on the western shore of Lake Michigan and gives residents the best of both worlds: the quiet, comfortable lifestyle of suburbia with the bustling city of Chicago and everything it has to offer only a short drive away. Winnetka is not only one of Illinois’s most affluent towns, but it is one of the country’s most lucrative neighborhoods as well, boasting a median property value of about $1.13 million. If you’re planning a move to Winnetka or just want to visit this picturesque town, here are four things to do in Winnetka to make sure you enjoy the charm of this special town.

If you’re coming to Winnetka from a big city like Chicago, you’ll instantly fall in love with how immersed the town is in the surrounding nature. Everywhere you go, you’ll find a background of luscious wooded areas or lakeside views. There are not only countless public parks to enjoy a stroll through, but for the more adventurous, Winnetka is home to rugged trails perfect for hiking, running, or biking. Some of the local favorites are the North Branch Trail, a 20-mile course enjoyed by horses and humans alike, and the Green Bay Trail, a 9-mile trail that weaves through storefronts, residential areas, and beach view paths. For a more slow-paced journey through nature, check out the Chicago Botanic Garden, which boasts 28 gardens and four “natural areas” over a massive 385-acre plot of land. Visitors can stroll the grounds or take a more hands-on approach and enjoy various programs and classes, or check out some of the libraries and laboratories on the grounds.

If you’ll be in Winnetka during the summer months, Lake Michigan offers all of the water activities that you can think of. Enjoy a walk down one of the many picturesque lakeside beaches, spend a day swimming, kayaking, or paddle boarding in the crystal blue water, or take a day to relax in a boat and sail around the beautiful coastlines. Lake Michigan is one of the most visited lakes in the country, and its beauty stands out as a truly special landmark. Any resident of Winnetka will be able to tell you just how much the lake adds to the atmosphere of the town. Lakeside views, abundant greenery, and crisp, fresh air come to define Winnetka, and those qualities help make it one of the most sought-after places to live in the whole country.

Whatever you’re craving, Winnetka offers a wide variety of restaurants to satisfy any pallet. The city has a diverse range of cuisines from all over the world that offer wonderful dining experiences. Many of the town’s restaurants are located just off Green Bay Trail, the popular walking path mentioned earlier that crosses through the city. Green Bay Trail is also just a couple of blocks away from the Lake Michigan shoreline, so you can enjoy a walk through the town or along the beach before finding a spot to dine for the night. Restaurants in Winnetka are known for their high-quality food and atmosphere and make for a perfect date night or dinner trip with the family.

Though you wouldn’t think that the small town of only 12,000 would be a major player in the entertainment industry, Winnetka is home to its own little slice of Hollywood and some important film history. A number of classic flicks were filmed in Winnetka, including Home Alone and Home Alone 2, the John Hughes films Ferris Bueller’s Day Off, Sixteen Candles, and Uncle Buck, as well as the Ben Stiller comedy Meet the Parents, in addition to a variety of other films and television shows. If you’re moving to Winnetka or just visiting and consider yourself a fan of any of these films, take a day to explore the city where they took place and discover locations where your favorite scenes were filmed. You can even retrace the steps of Ferris Bueller as he races through the neighborhood to return home or visit the home from Home Alone, but just remember that real people currently live in the home and all of the neighboring homes, so always be respectful of their privacy and boundaries.

Winnetka is over a century old, so the town holds a great deal of important history for both the state of Illinois and the whole nation. If you’re a fan of art, you’ll want to visit the Anita Willets-Burnham home, one of the oldest homes in the whole town and a wonderful representation of the artist’s life and work. For those interested in architecture, Winnetka has a deep history of architectural significance. As one of the most affluent towns in the nation, many famous architects of glory have left their mark on the city with unique and stunning homes, churches, and set pieces. Take a day to explore the area and take in the beauty of buildings that are both historically and architecturally significant.

Winnetka is one of Illinois’s most special and unique towns, offering residents the beauty of lakeside living with the convenience of a big city just a short drive away. If you are interested in learning more about Winnetka real estate, reach out to expert real estate agent Karen Stroble for more information about the town and to take your first steps in buying or selling in Winnetka.

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