Picture this: a quiet suburban morning on Chicago’s North Shore. The air is crisp, the sky pale blue, and there’s a soft crunch under your boots as you step outside. You can see your breath in the cold, and for a moment, everything feels still. Winter in the North Shore isn’t just about hibernating—it’s about slowing down, exploring, and finding new ways to enjoy the season right here at home.
Whether you live in Wilmette, Winnetka, Glencoe, Highland Park, or Evanston, there’s no shortage of things to do when temperatures drop. From sparkling light displays to frozen lakefront views, here are five local winter activities that make this season a little brighter.
Take a Winter Walk on the Green Bay Trail
Stretching almost nine miles from Wilmette to Highland Park, the Green Bay Trail follows the old Chicago & North Western rail line. It’s a scenic, easy path that feels completely different in winter—quiet, open, and peaceful.
You’ll pass through Kenilworth, Winnetka, and Glencoe, with glimpses of Lake Michigan and tree-lined neighborhoods along the way. Even a short 30-minute walk can clear your head.
Tip: Start in Wilmette (near Lake Avenue) or Hubbard Woods for easy parking. Bundle up with gloves and boots—snow-packed paths can be slick but beautiful.
Go Ice Skating at Centennial Ice Rinks (Wilmette)
Few things feel more winter-classic than ice skating. The Centennial Ice Rinks at 2300 Old Glenview Road in Wilmette offer indoor and outdoor skating, lessons, and open skate sessions for all ages. It’s a local favorite for families, date nights, or anyone looking to move after too much time indoors.
Why locals love it: The staff keeps the ice in great condition, there’s skate rental on-site, and it’s fun for both new and seasoned skaters.
Tip: Check public skate hours before you go and bring thick socks.
Experience “Lightscape” at the Chicago Botanic Garden (Glencoe)
Every winter, the Chicago Botanic Garden transforms into a wonderland for its Lightscape event. From mid-November through early January, you can stroll through glowing tunnels of lights, illuminated trees, and art installations synced to music.
Located at 1000 Lake Cook Road in Glencoe, it’s one of the North Shore’s most magical winter experiences—and it sells out fast each year.
Why it’s special: You get the beauty of nature mixed with festive artistry. It’s perfect for kids, couples, and anyone who needs a little holiday cheer.
Tip: Buy tickets early at chicagobotanic.org. Go right after sunset for the best photos. Parking is on-site, but arrive 20 minutes early—it can get busy.
Enjoy the Lakefront in Winter
If you’ve ever seen Gillson Park in Wilmette or Lloyd Beach in Winnetka during the colder months, you know how breathtaking it can be. The lake turns a steely gray, the waves crash against icy rocks, and the quiet stretches of shoreline feel peaceful and raw.
A simple walk along Sheridan Road or through Elder Lane Beach in Winnetka gives you incredible winter views of Lake Michigan. Bring a camera—you’ll capture reflections and frozen edges you can’t see in summer.
Tip: Dress for wind—it’s colder by the lake! Stop afterward for coffee or soup at Central Station Coffee & Tea in Wilmette or Hometown Coffee & Juice in Glencoe to warm up.
Try Local Ice Rinks and Sledding Hills
You don’t need to travel far for winter fun. The North Shore is full of community rinks and sledding spots that open when weather permits:
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Meadowhill Park (Northbrook) – A favorite sledding hill with lots of open space.
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Tower Park (Northbrook) – A gentle hill perfect for younger kids.
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Lake Bluff Park District Rink – Outdoor rink that opens when temperatures stay below freezing.
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Winnetka Park District Rink – Check for open skate times or bring your own gear when conditions allow.
Tip: For sledding, always check conditions first and wear helmets for kids. Most parks post updates online about when rinks or hills are safe to use.
Final Thoughts
Winter doesn’t have to be something to get through—it can be something to embrace. On Chicago’s North Shore, you don’t need fancy gear or a long drive to enjoy the season. A lakeside walk, a spin on the ice, a glowing light show, or a sled ride down a snowy hill—these small experiences create big memories.
So zip up your coat, grab your mittens, and make the most of this beautiful corner of Chicagoland this winter.
Thinking About Making the North Shore Your Home?
If you’re dreaming of living closer to the lake, near top schools, and within walking distance of coffee shops and community parks, the North Shore is truly magical in every season.
I’m Sarah Jividen, a Realtor® with @properties Christie’s International Real Estate, and I help families find their forever homes across Chicago’s North Shore—including Wilmette, Winnetka, Glencoe, Evanston, and beyond.
Reach out anytime for local insights, neighborhood guides, or to start your home search.
📩 SarahJividen.com | 📱 @SarahJividenRealEstate
