Discover Chicago’s 606 Trail (Bloomingdale Trail): Your Ultimate Local Guide

If you’ve been looking for the perfect city escape, the Chicago 606 Trail — also known as the Bloomingdale Trail — is one of the coolest hidden gems in the city. I finally made time to explore it, and it instantly became my new happy place.

Chicago’s Answer to the NYC High Line

Built along an old elevated train line, this 2.7-mile greenway winds high above the Northwest Side, connecting neighborhoods like Wicker Park, Bucktown, Logan Square, and Humboldt Park. I’d seen photos for years but never realized how magical it feels in person — peaceful, vibrant, and so Chicago.

Last Tuesday, under blue skies and sunshine, I finally walked it end-to-end. Let me tell you — it completely blew me away.

Stepping onto the trail from a ramp in Bucktown, I felt like I’d entered a secret world. One minute you’re on busy city streets; the next, you’re twenty feet up, surrounded by wildflowers with the hum of Chicago below.

Now that I’m hooked, here’s my complete guide to planning your own amazing 606 Trail adventure.

🚶‍♀️ So, What Is the 606 Trail, Anyway? (A.K.A. the Bloomingdale Trail)

If you’re wondering “What is the 606 Trail?” — here’s the scoop. The 606 Trail, officially known as the Bloomingdale Trail, is a 2.7-mile elevated park and greenway built on an old freight rail line. The name “606” comes from the shared prefix of the Chicago zip codes it runs through, like 60622 and 60647.

It opened in 2015 and connects four of Chicago’s most vibrant neighborhoods: Wicker Park, Bucktown, Logan Square, and Humboldt Park. The trail is managed by the Chicago Park District and was designed to bring together art, nature, and community — Chicago’s brilliant answer to New York’s High Line, but with a totally unique, laid-back local vibe.

You’ll find joggers, cyclists, dog walkers, artists sketching, and families out for a stroll. It’s one of those rare places where you can feel the pulse of the city and the calm of nature all at once.

My Favorite Can’t-Miss Stops on the 606

Here’s what made my trip so special — the little discoveries along the way.

🌸 Humboldt Overlook

My favorite place to pause. It features a colorful mural and benches where you can look out over tree-lined Humboldt Boulevard. Perfect for photos and skyline views.

🎭 Damen Arts Plaza

A lively area near the Damen Avenue access point with rotating sculptures, murals, and bleacher seating — an ideal people-watching spot.

🌅 Exelon Observatory

On the western end of the trail, this spiraling overlook marks the solstices. It’s especially beautiful at sunset.

🚲 The Art & Gardens

The whole trail is a living gallery! You’ll see native landscaping that changes with the seasons, plus ongoing public art installations that keep things fresh.

🗺️ Your 606 Trail Planning Cheat Sheet (How to Visit)

Here’s the practical stuff I wish I’d known before I went — everything you need to make the most of your day.

📍 Access Points to the 606 Trail

There are over a dozen gentle ramps every few blocks (no stairs needed). The easiest ones to start at are:

• Walsh Park – 1722 N. Ashland Ave. (Bucktown)
• Churchill Field Park – 1800 N. Damen Ave. (Wicker Park)
• Humboldt Overlook – For great views right away
• Ridgeway Avenue – Western end near the Exelon Observatory

💡 You can check the official 606 Trail map to find the entrance closest to your hotel, coffee shop, or Divvy station.

🚗 Getting There & Parking:

• Public Transit: Take the CTA Blue Line to Damen or California — both are short walks from the trail.
• Divvy Bikes: My favorite way to explore! Stations are scattered all along the route.
• Parking: Limited street parking in Wicker Park and Logan Square — be prepared to walk a few blocks.

♿ Accessibility:

The trail is completely wheelchair- and stroller-friendly with smooth ramps and wide paths.

📜 Quick Rules & Trail Etiquette:

• ✅ Allowed: Walking, running, biking, and non-motorized scooters.
• 🚫 Not allowed: E-scooters (sorry, Lime fans).
• 🔔 Cyclists: A friendly ring of your bell before passing is always appreciated!

🕒 When to Go for the Best Experience

It really depends on what kind of vibe you’re after. Be sure to bring water — there’s limited shade in summer and few drinking fountains along the path.

.🌅 For Peace & Quiet: Weekday mornings are calm and serene — perfect for reflection or photography.
🎡 For Energy & People-Watching: Weekend afternoons are bustling and fun, full of families, music, and local life.
✨ For the Best Light: Golden hour, just before sunset, is absolutely magical — especially near the Exelon Observatory.

🍁 Seasonal Tip: Fall colors and spring blooms are stunning along the trail, while winter walks can be surprisingly peaceful (just bundle up!).

Make a Day of Your Visit to the Bloomingdale Trail: Food, Coffee & Nearby Gems

The 606 is incredible, but the surrounding neighborhoods with amazing bakeries and restaurants are half the fun. Here’s how to turn your walk into a full Chicago day out.

East End (Bucktown / Wicker Park):

• ☕ Dayglow Coffee – Amazing pour-overs and creative drinks near the Walsh Park entrance.
• 🎨 Trailhead Murals – Check out the art right at the Bucktown trail entrance.
• 🍕 Six Corners Intersection (Milwaukee, Damen & North) – Wicker Park’s lively hub packed with restaurants, boutiques, and bars.

Midpoint (Logan Square):

• 🎭 Damen Arts Plaza – Rotating sculptures and murals with plenty of seating.
• 🚲 Divvy Bike Station – Hop on for a breezy ride westward.

West End (Humboldt Park):

• 🌸 Humboldt Overlook – Gorgeous mural and skyline views.
• 🧱 “Yellow Brick Road” Sidewalk – A short walk south leads to this whimsical tribute to The Wizard of Oz author L. Frank Baum, who lived nearby.

I ended my visit wandering through Humboldt Park before grabbing a slice in Wicker Park — the perfect finish to a perfect Chicago day.

Why You’ll Love the 606 Trail

Walking the 606 Trail gives you a whole new perspective on Chicago. It’s a reminder that nature and creativity can thrive right above the city streets.

Whether you’re a lifelong local or planning your first Chicago visit, the 606 Trail is a must-do. It’s free, beautiful, and unforgettable. I’m already planning my next trip back — this time with my bike. Maybe I’ll see you out there!

📍 Quick Facts

📌 Pin It for Later

Planning a future Chicago adventure? Save this guide to your travel board so you’ll remember to walk (or bike!) the 606 next time you visit.