🏙️🛤️ Milwaukee Ave Uncovered: Trails, Towers & Treasures 🚶♂️🌆
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🏙️🛤️ Milwaukee Ave Uncovered: Trails, Towers & Treasures 🚶♂️🌆
A Saturday fall stroll through River West, Noble Square & Wicker Park
☀️ I know we just had some snow, but it’ll be MUCH warmer this weekend — and it is still good walking weather, so let’s make the most of it! 🚶♀️🌆 We’re ending the season with another great neighborhood adventure!
Take a historical stroll down one of Chicago’s oldest streets — while the weather’s still walking-worthy!
Walk the old Native path, check out iconic Polish churches, and uncover stories of long-gone shops that made this street famous.
Ready to step off the grid and onto one of Chicago’s oldest, boldest streets? Join us for a guided walk down Milwaukee Avenue — a diagonal slice of city life with layers of history. From Indigenous trails and Polish cathedrals to vanished department stores and reborn landmarks, we’ll explore how this vibrant corridor keeps reinventing itself.
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🗓️ Saturday, November 15, 2025
🕚 12:00 PM – 2:20 PM
📍 Start: Germain House, 729 N. Sangamon St.
🎯 End: The Robey Hotel, 2018 W. North Ave. (~2.5 miles total)
💰 Cost: $20 (cash preferred; Zelle, Venmo, PayPal accepted)
🚶♀️ Casual pace | Entirely outdoors
⚠️ Note: Walk ends 2.5 miles from the start — if driving, consider parking near the midpoint! Or hop the L or a bus back.
☀️ A casual, curiosity-filled outing for lovers of Chicago stories, old and new.
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🔍 What You’ll See & Learn:
✅ One of Chicago’s oldest trails — from Native path to Polish main street
✅ Grand churches, vanished businesses, reborn banks, and funky artist spaces
✅ Architectural eye candy paired with deep neighborhood stories
✅ The ever-evolving tale of immigrant hustle, urban reinvention, and civic pride
📸 Not a photo walk, but you’ll want your camera!
🎤 Led by your passionate, ever-curious guide (that’s me!) — perfect for architecture buffs, history lovers, and anyone who wants to be a tourist in their own city.
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🗺️ Route Highlights (subject to change):
🏠 Germain House – Queen Anne gem
⛪ St. John Cantius – A Polish baroque beauty
⛪ St. Boniface – Towering twin-spired ghost
🌳 Eckhart Park – A community anchor
🏛️ Polish Museum of America – A cultural time capsule
🕍 Holy Trinity – Where grandeur meets grit
⛪ St. Stanislaus Kostka – The original Polish cathedral
🌿 Pulaski Park – WPA charm in a leafy square
🧠 National Alliance – Mid-century mission hub
🏦 Home Bank & Trust – Financial strength in stone
🏬 Wieboldt’s (former) – Lost department store legend
🎨 Indigo Lofts – Wallpaper meets art lofts
🎭 Flatiron Arts – Boho central
🏛️ Noel State Bank – Walgreens with a dome
🏨 The Robey – A tower of transit turned trendy hotel
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🏙️ Fun Facts Along the Way:
💬 Milwaukee Ave began as a Native trail, then became a plank-lined toll road
🚌 Streetcars once zipped through what’s now rush-hour traffic
🎨 Wicker Park’s art scene exploded here in the ’80s
🍺 Expect tales of beer barons, preservation fights, and colorful characters
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📌 Quick Logistics:
✔️ Start near Grand Blue Line
✔️ End near Damen Blue Line
✔️ Wear good walking shoes & bring water
✔️ DM or email with questions
✔️ Tour runs rain or shine! 🌦️
👟 What to Bring:
• Comfortable walking shoes
• Water bottle
• Weather-appropriate attire
• $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo, PayPal accepted)
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🍽️ Optional Lunch After the Tour
Stick around and grab a bite at one of these local favorites:
• 🥗 Sultan’s Market – casual Middle Eastern eats
• 🥪 CAVA – build-your-own Mediterranean bowls
• 🍕 Paradise Park – funky patio vibes + pizza
• 🌮 Big Star – beloved taco + whiskey joint
💵 Bring cash for lunch — some spots don’t split checks!
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🧭 Come walk where the old city still hums — Milwaukee Ave is calling.