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See all- ๐๏ธ๐ค๏ธ Milwaukee Ave Uncovered: Trails, Towers & Treasures ๐ถโโ๏ธ๐Germain House, Chicago, IL
๐๏ธ๐ค๏ธ Milwaukee Ave Uncovered: Trails, Towers & Treasures ๐ถโโ๏ธ๐
A Sunday stroll through River West, Noble Square & Wicker Park
Walk the old Native path, check out iconic Polish churches, and discover stories of long-gone shops that made this street famous.
Ready to step off the grid and onto one of Chicagoโs oldest, boldest streets? Join us for a guided walk down Milwaukee Avenue โ a diagonal slice of city life with layers of history. From Indigenous trails and Polish cathedrals to long-lost department stores and reborn landmarks, weโll explore how this vibrant corridor keeps reinventing itself.
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๐๏ธ Sunday, August 3, 2025
๐ 11:45 AM โ ~1:45 PM
๐ Start: Germain House, 729 N. Sangamon St.
๐ฏ End: The Robey Hotel, 2018 W. North Ave. (~2.5 miles total)
๐ฐ Cost: $20 (cash preferred; Zelle, Venmo, PayPal accepted)
๐ถโโ๏ธ Casual pace | Outdoors |
โ ๏ธ Note: Walk ends 2.5 miles from the starting point โ if driving, consider parking near the midpoint! Or take the bus or the L train backโ๏ธ A casual, curiosity-filled outing for lovers of Chicago stories, old and new.
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๐ What Youโll See & Learn:
โ One of Chicagoโs oldest trails โ from Native path to Polish main street
โ Grand churches, vanished businesses, reborn banks, and funky artist spaces
โ A mix of architectural eye candy and deep neighborhood stories
โ The ever-evolving story of immigrant hustle, urban reinvention, and civic pride๐ธ Not a photo walk, but youโll want your camera
๐ค Led by your passionate, ever-curious guide (thatโs me!) โ this oneโs for architecture buffs, history lovers, and anyone who wants to be a tourist in their own city.
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๐บ๏ธ Route Highlights:
๐ Germain House โ Queen Anne gem
โช St. John Cantius โ A Polish baroque beauty
โช St. Boniface โ Towering twin-spired ghost
๐ณ Eckhart Park โ A community anchor
๐๏ธ Polish Museum of America โ A cultural time capsule
๐ Holy Trinity โ Where grandeur meets grit
โช St. Stanislaus Kostka โ The original Polish cathedral
๐ฟ Pulaski Park โ WPA charm in a leafy square
๐ง National Alliance โ Mid-century mission hub
๐ฆ Home Bank & Trust โ Financial strength in stone
๐ฌ Wieboldtโs (former) โ Lost department store legend
๐จ Indigo Lofts โ Wallpaper meets art lofts
๐ญ Flatiron Arts โ Boho central
๐๏ธ Noel State Bank โ Walgreens with a dome
๐จ The Robey โ A tower of transit turned trendy hotel***
๐๏ธ Fun Facts Along the Way:
๐ฌ Milwaukee Ave started as a Native trail, then a plank-lined toll road
๐ Streetcars once zipped through whatโs now rush-hour traffic
๐จ Wicker Parkโs art scene exploded here in the โ80s
๐บ Expect tales of beer barons, preservation fights, and colorful characters***
๐ Quick Logistics:
โ๏ธ Start near Grand Blue Line
โ๏ธ End near Damen Blue Line
โ๏ธ Wear good walking shoes & bring water
โ๏ธ DM or email with any questions
โ๏ธ Tour runs rain or shine ๐ฆ๏ธ***
๐ What to Bring:
โข Comfortable walking shoes
โข Water bottle
โข Weather-appropriate attire
โข $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo, PayPal accepted)๐ฝ๏ธ Optional Lunch After the Tour
Stick around and grab a bite at one of these local favorites after the walk:
โข ๐ฅ Sultanโs Market (Wicker Park) โ casual Middle Eastern eats
https://www.sultansmarket.com/
โข ๐ฅช CAVA (Wicker Park) โ build-your-own Mediterranean bowls
https://cava.com/locations/1611-n-damen-ave-chicago-il
โข ๐ Paradise Park โ funky patio vibes + pizza
https://www.paradiseparkchi.com/
โข ๐ฎ Big Star โ beloved taco + whiskey joint
https://www.bigstarchicago.com/๐ต Bring cash for lunchโsome spots donโt split checks!
๐งญ Come walk where the old city still hums โ Milwaukee Ave is calling.