The 606

Description

There’s just something about the 606 that makes me pause for a second and soak in what’s around me, even if I’m huffing up a sweaty jog or walking the dog who keeps wanting to sniff every last patch of grass. The 606 is Chicago’s quirk-fueled, up-in-the-air greenway – a sort of urban playground layered over an old, sleepy railroad track. Just imagine: 2.7 miles worth of lush, landscaped trail gently winding its path over city streets, connecting neighborhoods that would rather not be separated in the first place. Bikes whiz by, strollers trundle along, and there’s always a pack of runners chasing that runner’s high (or maybe they just want a donut from one of the cafes nearby; who knows).

I remember my first hike here — a muggy June afternoon, goose bumps still lingering from the latest summer storm. It’s almost weirdly peaceful, being lifted a little above the chaos, surrounded by planters bursting with prairie grasses, public art peeking from corners, and the reassuring click-clack of skateboard wheels. Look around and you’ll see families, tired office workers losing the tie and letting their hair down, and kids ricocheting from the skate park or pausing to peer over the edge. Unlike the lakefront trail (which is stunning, don’t get me wrong), the 606 feels neighborly, scrappy, and surprisingly leafy for its urban address.

Is it perfect? Not at all. Sometimes it gets a little crowded on a Saturday, and I wish some of the views were a tad less “industrial.” But then there’s that joy of catching a sunset near Humboldt Boulevard, hearing laughter drift up from open windows, and realizing how this rail line has transformed into a green lifeline for whole communities.

Key Features

• Elevated Trail Adventure: The 606’s crowning achievement is its elevation — cruising high above city streets, giving you an entirely fresh take on Chicago’s grit and charm. The perspective alone is worth a visit.
• Length and Layout: The straight-ish, point-to-point route stretches 2.7 miles, making it doable for even casual walkers. (But, if you’re feeling mighty, just double back and call it a marathon.)
• Landscaped Beauty: This isn’t the wild forest, but it’s gorgeously designed with native prairie plants, wildflowers, and plenty of shady benches for the breaks we all need.
• Wheelchair Accessibility: Entrances and parking are wheelchair-friendly — so everyone gets to enjoy the Chicago sky and sunshine up here.
• Active Vibes: Walking, biking, jogging, dog-walking, stroller-pushing — all energy levels welcome. Skateboarding is encouraged in the dedicated area, too. It’s good for families, solo travelers, or the energetic toddler crew.
• Dog Park: Dog lovers, rejoice. Bring your four-legged pal; the 606 is very much dog-friendly, just keep that leash snug and scoop after your pup, please.
• Public Art and Murals: Chicago’s art comes alive here, tucked into corners and sometimes sprawling across entire bridge underpasses. My favorite? The mosaic at the western end, quietly shouting “You made it!”
• Accessible Fun for Kids: Kid-friendly trail features and adjacent parks make it honestly such a good option for burning off energy on the weekend or after-school hours.
• Neighborhood Connections: You’ll pass through Logan Square, Humboldt Park, Bucktown, and Wicker Park, each flaunting its own set of bakeries, coffee shops, and architectural oddities. Makes snack breaks dangerously easy.

Best Time to Visit

People ask all the time—when’s the best moment to hit up The 606? Let me level with you. If you’re a fan of room to breathe, weekday mornings (before 10am) are magic. Sunrises here, cutting through early mist and lighting up the wildflowers—chef’s kiss. Push your luck on a sunny Saturday afternoon and you might end up in more of a people parade, but that’s kind of its charm too if you’re a people watcher. Usually, late spring through early fall serves up the sweet spot: blooming meadows, manageable crowds, and weather that won’t leave you feeling like a popsicle or a puddle.

Summer evenings, though, are almost cinematic. The golden hour bathes the entire trail in soft, honeyed light, and there’s this gentle city hum that sort of lifts your mood. That said, late autumn can be heartbreakingly pretty, too, when the trail glows with burnt oranges and deep reds. In winter, it’s quiet, stark, even a bit haunting — perfect if you’re a brisk walker who loves crispy air and fewer folks getting in your way. Plus, let’s not forget: Chicagoans are tough. Cold doesn’t stop us, it just means we layer up and walk faster!

How to Get There

Okay, here’s the short version: If you’re anywhere in Chicago with a CTA card (honestly, even if you don’t have one), you can get to The 606 without breaking a sweat. Several “access points” line the stretch, so you’ve got options galore — which is honestly my favorite part if I want to sneak in a half-hour walk after grabbing groceries.

Public transit-wise, the Blue Line practically hugs the eastern end, and multiple bus routes get you within blocks of most entrances. Uber, Lyft, or cabs are always on standby (sometimes horn-happy, but that’s Chicago). If you’re driving, fair warning: parking in some neighborhoods—looking at you, Wicker Park—can be, um, a lesson in patience. But there are wheelchair accessible parking spots for those who need them. My tip? Street parking west of Humboldt usually feels less cut-throat.

If you’re brave on two wheels, bike there! The city’s got Divvy stations aplenty, and you can even hop right on the trail from your own neighborhood if you’re local. Signage is generally good, not perfect, so pay a little attention if, like me, you sometimes walk straight past the clearly marked entrance while squinting at your phone.

Tips for Visiting

• Timing is (Almost) Everything: Want the trail to yourself? Go early or on weekday evenings. Midday weekends can feel like rush hour on legs — not terrible, just plan accordingly (especially if crowds make you twitchy).
• Bring Water, Sunscreen, and Curiosity: The trail is mostly exposed, so protect your skin and stay hydrated. And bring a camera, or at least your phone, because some of the skyline views and murals kind of beg to be Instagrammed.
• Keep an Eye on Your Stuff: This is still a city, with all the normal city wisdom in play: bag zipped, wallet close, bike locked. Never hurts to err on the side of caution, right?
• Mind the Trail Etiquette: Cyclists, let folks know before zipping past. Runners, stick to the right if possible. Everyone, be cool — share the green space. I once saw a group of children in a wagon get overtaken by a rollerblader in a banana suit (not kidding), and it ended in high-fives and giggles. So — expect the unexpected, but be courteous.
• Explore the Neighborhoods: Don’t just sweep through. The cafes, bakeries, and corner stores just off the trail are basically “Choose Your Own Adventure” stops. I discovered my favorite empanada shop that way — and yes, it’s as good as you’re picturing right now.
• Travel Light – and Be Flexible: The 606 isn’t Everest. But if you’re planning on making it to both ends and back, pack light and wear good shoes. Don’t sweat it if you only manage half the distance. The joy is in the journey, not the finish line.
• Bring the Whole Crew: Dogs, kids, friends. The 606 really is best as a shared experience. Dog bags for clean-up are must-haves, and the kid-friendly ramps and access points mean there aren’t many excuses to leave anyone behind.

Above all else, let yourself wander. That’s the sweet spot here: not rushing from A to B, but soaking in the wild mix of city, art, and nature that somehow works together. Take your time to chat with a local, watch the city skyline flicker in afternoon sun, and maybe — just maybe — make a tradition out of grabbing a snack on every trip. Don’t be surprised if you end up wishing this old rail line was in your hometown, too.

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