10 Bucket List Things to See and Do in Winnetka & Glencoe

Nestled along the shores of Lake Michigan north of the city of Chicago are Winnetka and Glencoe, two vibrant suburban communities with plenty to offer — whether you’re looking to find a new home and settle in for the long haul, or simply enjoy a few hours in Chicagoland.

Full of beautiful parks, wonderful community centers, and interesting homes, Winnetka and Glencoe are two of the standout neighborhoods in Chicagoland’s North Shore area. But what should be on your bucket list of things to see and do in these charming villages?

Here are ten of the “can’t miss” sights, attractions, and experiences that make Winnetka and Glencoe special:

1.) Travel Back in Time with the Winnetka Historical Society

The Winnetka area is full of rich history and incredible stories, and there’s nowhere better to learn about the region’s past and future than at the Winnetka Historical Society. Since 1932, this organization has been chronicling the history of Winnetka and its surrounding communities, in order to preserve this crucial knowledge and pass it down to future generations. Today, the Historical Society operates a museum out of a stunning Gothic Revival building, as well as the Schmidt-Burnham Log House, which offers visitors the chance to see firsthand what the community would have been like in the 1830s.

For more on the Winnetka Historical Society or to plan your visit, you can read on at the organization’s official site, here.

Log cabin. Photo credit: Teemu08 via Wikimedia Commons

2.) See a Play at the Writers Theatre

Just a short distance away from the Glencoe Metra station is another spot sure to whisk visitors away to entirely new places — in this case, through the magic of live performance. For more than 25 years, the Writers Theatre in Glencoe has produced exhilarating productions of classic and contemporary plays and musicals. Today, the Writers Theatre is known nationwide as one of the best theatre companies in America. For an additional thrill, get to the performance space a little early, so you can marvel at the Writers Theatre’s gorgeous, thoroughly modern architecture.

To learn more about the history of Writers Theatre or see what’s on stage next, you can visit the company’s official site here.

3.) Enjoy One of the Area’s Signature Trails

One of the great things about the North Shore neighborhoods of Glencoe and Winnetka is their close proximity to nature. As locals will tell you, one of the best ways to get outdoors and enjoy a beautiful day is to take to one of the area’s world-renowned biking, hiking, or running trails. The 9-mile Green Bay Trail runs parallel to the Metra line that cuts across Winnetka and Glencoe, for instance, and offers a great way to escape from the world for an hour or two. Nearby, following the paths of the 21-mile North Branch Trail allows you to weave around other beautiful natural sites, including the Skokie Lagoons and Erickson Woods.

4.) Get Immersed in Nature at the Chicago Botanic Garden

The Chicago Botanic Garden is a true wonder. This sprawling natural complex spans out across 385 acres of land and includes 27 gardens and four natural areas, housed on nine distinct islands. Home to nearly 3 million plants, the Botanic Garden is a popular getaway for tourists and locals alike. With special events and informative classes held throughout the year, there’s never an off-season in this one-of-a-kind living museum.

To begin exploring the Botanic Garden, you can visit its official site, available here.

Chicago Botanic Garden sculpture

5.) See Famous Architecture In Action

Chicagoland is famous for its high concentration of Prairie-style architecture, a design style popularized and perfected by Frank Lloyd Wright. The neighborhoods around Glencoe and Winnetka are home to some iconic examples of this world-famous style, including a few structures by Wright himself — the Sherman Booth Cottage and the William Glasner House. To complete your architectural trail, swing by the Orth House, a historic landmark designed by Walter Burley Griffin, one of Wright’s most accomplished acolytes.

6.) Savor Lake Michigan from the Beach

Do you hear Lake Michigan calling your name? Whether your idea of a perfect summer day is taking a dip in the crystal clear waters or simply lounging with a good book in the sand, there are plenty of beachside spots sure to satisfy around Winnetka and Glencoe. In Winnetka, for example, Tower Road Beach offers easy access to the lakefront. To the north, Glencoe Beach offers a stunning place to enjoy the water, as well as easy access to Perlman Boating Beach, where mariners can launch their boats for a day on the waves.

7.) Enjoy One of the Area’s Many Local Parks

If you’re looking for somewhere to stretch your toes into the grass, toss a frisbee with friends, or let your little ones play, there’s no place like the park. The Winnetka Park District and Glencoe Park District are full of unique options perfect for letting you wile away the hours, including standouts like Hubbard Woods Park and Crow Island Woods.

8.) Lace Up Your Skates at a Local Ice Rink

Whether you want to perfect your pirouette or simply glide the day away, both Winnetka and Glencoe are home to unique spots for ice skating. Whether a seasoned skating expert or an amateur as fresh as a rink right after the Zamboni glides by, you’ll want to add Winnetka Ice Arena and Watts Ice Center to your “must-try” list.

Operated by the Glencoe Park District, Watts Ice Center takes over several acres of Watts Park throughout the winter season. You can learn more about it here, via Facebook. The Winnetka Ice Arena is a year-round facility, offering public skate times, private lessons, and more. To find out more, visit the Arena’s official site, here.

9.) Hit the Links at a Local Golf Club

If golf is your game, Winnetka and Glencoe are both home to prime spots for playing a few holes and honing your skills. Originally designed in 1914 as a 9-hole course, today the Winnetka Golf Club offers 18 holes spanning 6,472 yards, nestled up against the beautiful boundaries of the Cook County Forest Preserves. The facility also includes practice areas, like a 26-station driving range. Not far away, the Glencoe Golf Club boasts a historic 18-hole course and a state-of-the-art practice center, supported by a partnership between the Village of Glencoe and the Forest Preserve District of Cook County.

10.) Kick Back at a Cozy Cafe

Sometimes, the best way to spend a morning is to sip a delicious cup of coffee or tea, while snacking on breakfast at a cozy local spot. When you’re in the mood to enjoy a few hours kicking back, or you simply want to grab a tasty cup of java to go, Winnetka and Glencoe have plenty of local gems sure to have what you’re looking for. For a true local experience you won’t get anywhere else, try a beloved neighborhood spot like Meg’s Cafe, Hometown Coffee & Juice, or Reprise Coffee Roasters.

Want to talk to an expert who knows the North Shore inside and out? Get in touch with us today!

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