Winnetka

Winnetka takes its name from a Native American word for "beautiful land," and it earned that description early: German settler Michael Schmidt arrived in 1826, and by 1854 the Chicago and Milwaukee Railroad, championed by village co-founders Charles Peck and Walter Gurnee, had laid track through town, cementing Winnetka's future as one of the North Shore's first true railroad suburbs. Growth stayed deliberately slow and careful, from a population of 584 in 1880 to under 2,000 by 1900, before more than tripling to nearly 6,700 by 1920 as the North Shore's commuter appeal took hold. That same unhurried, planned approach shaped the village that exists today: wide lawns, historic homes spanning more than a century of North Shore architecture, and a compact, walkable Elm Street downtown of independent shops and cafes rather than chains. The Winnetka Historical Society still actively documents the lesser-known people and places behind that 200-year history, a sign of how seriously the village guards its small-town character even as it sits just 16 miles from downtown Chicago. Add in excellent schools, several Lake Michigan beaches, and the nearby Chicago Botanic Garden, and Winnetka reads less like a suburb and more like its own well-tended small town on the lake.

Parks & Recreation

Skokie Lagoons

The Skokie Lagoons are an 894 acre forest preserve of seven interconnected lagoons, dug by the Civilian Conservation Corps between 1933 and 1942 and now one of the North Shore's biggest outdoor destinations. Access from Winnetka runs off Tower Road just east of I-94, where a trailered boat launch and a seasonal canoe and kayak rental concession open onto more than 11 miles of shoreline; bluegill, sunfish, and largemouth bass draw anglers along the banks nearly year round. A roughly 4.4 mile paved loop circles the water for walking, running, and biking, and the preserve's mix of open lagoon and wooded shoreline makes it a reliable spot for birdwatching in every season.

Beach & Lakefront

Elder Lane Beach

Elder Lane Beach is Winnetka's classic Lake Michigan swimming beach, a stretch of sand at the foot of a restored bluff where lifeguards staff the water through the summer season. After a multi year cleanup and restoration effort, the beach reopened for full swimming access for the 2026 season, with native plantings along the bluff above improving both the lake views and the shoreline's long term stability. A seasonal pass covers Elder Lane along with Winnetka's other beaches, or admission can be paid daily at the gate, and the beach house has restrooms and a spot to rinse off after a swim. It is a genuine small town beach day, close enough to treat as a regular part of summer rather than an occasional outing.

Parks & Recreation

Green Bay Trail

The Green Bay Trail is an 8.9 mile paved path built on the old Chicago North Shore and Milwaukee Railroad right of way, running from Wilmette north through Winnetka, Hubbard Woods, Glencoe, and on to Highland Park. Wide, flat, and wheelchair accessible, it is used year round for walking, running, biking, and in winter for cross country skiing, with benches, picnic spots, and parking access scattered along its length in each town it passes through. Because it threads right along the Union Pacific tracks, it doubles as the most pleasant possible walking or biking route between downtown Winnetka and Hubbard Woods, a shaded, car free corridor that locals use as much for the commute as for the exercise.

Parks & Recreation

Winnetka Golf Club

Winnetka Golf Club is a public 18 hole course run by the Winnetka Park District on land that golf architect William Langford first laid out in 1914, turning 30 acres of flood plain marsh into the club's original nine holes before the park district doubled it to a full eighteen in 1922. A 2022 renovation by architect Rick Jacobson addressed decades of recurring flooding while keeping the course's tree lined, William Langford era character intact, and today it plays 6,517 yards from the back tees with a 72.6 rating across four sets of tees for every skill level. Beyond the championship course, the club runs a nine hole par 3 layout, a 28 stall lighted driving range, three practice greens, and a full instructional program, making it as approachable for a quick evening round as it is for a serious game.