What we’re about
🍷 Welcome to Windy City Wine+!
We’re a social crew of wine, food, and spirits lovers exploring Chicago’s best sips and bites—plus fun excursions to new venues and festivals around the city (and sometimes beyond 🍇).
I’m Giovina, your organizer as of 9/10/23, taking over from Tom Besore. We'll keep our beloved Millennium Park summer wine nights and add year-round events like wine dinners, classes, tastings, festivals, and vineyard trips.
I also run 1001 Things to See in Chicago Before You Die—an active sister group with 4–5 events weekly. Check it out!
Questions or ideas? Message me anytime on Meetup!
– Giovina Romandine, Organizer 🍷
Upcoming events (4+)
See all- 🥨🍺 Beer, Brats & Beats: 103rd Chicago Oktoberfest! 🎷🎉Across from "The Old Town School of Music", Chicago, IL
🥨🍺 Beer, Brats & Beats: 103rd Chicago Oktoberfest! 🎷🎉
Step into a century-long tradition at the 103rd Annual Chicago German-American Oktoberfest in Lincoln Square!
📅 Date: Friday, 9/5/25
🕒 Time: 6–10 PM 🎶🥨
📍 Meet Spot: 4521 N. Lincoln (Across from "The Old Town School of Music")Enjoy authentic German food 🍖🥨, dance to live German bands 🎵💃, and explore festive vendors! Admission is FREE! This year’s fest was nominated in the USA Today 2024 10Best Readers’ Choice awards. Always a fall favorite of the group!
🎵 Bands performing:
…and more!
🎉 Festival highlights:
- Opening Ceremony: 8 PM Friday
- Von Steuben Parade: 2 PM Saturday
- Free 3-day festival (we’re attending Friday!)
🌟 Festival info: Chicago German-American Oktoberfest
🚇 Public transit: Easily accessible via bus & train. Plan your trip here: CTA Trip Planner
🚗 Driving/Parking: Metered spots on Western, Lincoln, Lawrence & Irving Park. Limited side street parking; watch for permit-only areas.❗ No-show policy:
- 3 no-shows without updating RSVP = 3-month freeze on future events
- Update RSVP by start time or message host if late
- Check in with host when you arrive
Let’s celebrate Chicago’s German-American heritage with food, music, and friends! 🍻🎶🥨
- 🌴🥁 Paseo Boricua & Humboldt Park: Stories, Murals & Monuments w/ Eduardo 🎨The National Museum of Puerto Rican Arts & Culture, Chicago, IL
🌴🥁 Paseo Boricua & Humboldt Park: Stories, Murals & Monuments w/ Eduardo 🎨
Let's explore the Paseo Boricua, the National Museum of Puerto Rican Arts & Culture, and Humboldt Park with Eduardo! ✨
📆 Saturday, September 6, 2025
⏰ 12:00 PM – 2:00 PM
👣 Approx. 1.5 miles of walking
💵 Cost: $30 per person (cash preferred; Zelle/Venmo/PayPal accepted)
👉 Cost includes museum entrance | Please pay at the start of the tour
🌦️ Casual pace | Outdoors | Rain or shine
⚠️ Walk ends ~6 blocks from start — plan parking accordingly🥁 Join us for an exciting tour led by our special guide, Eduardo! Experience a vibrant journey along Paseo Boricua, where you'll discover stunning murals, significant monuments, and the rich Puerto Rican pride that define Humboldt Park. As a highlight of the tour, we will also step inside the National Museum of Puerto Rican Arts and Culture for an unforgettable experience. Don't miss out!! 🎨🌴
This is a special cultural walking tour of Chicago’s Puerto Rican heart—led by longtime resident & guide Eduardo Arocho! Eduardo has been giving tours for over 29 years and runs his own Paseo Boricua Tour Company. He’ll bring to life the art, history, and community stories of Humboldt Park & Division Street (a.k.a. Paseo Boricua).
🌟 Why Walk Humboldt Park?
This area has been a longtime home to Chicago’s Puerto Rican community.🇵🇷 Paseo Boricua – You’ll know you’re in Humboldt Park when you pass under one of the monumental Puerto Rican flags that serve as gateways into the neighborhood. These 59-foot steel flags, installed in 1995, mark the boundaries of Paseo Boricua (loosely translated as “Puerto Rican Promenade”).
This vibrant stretch of Division Street has transformed over several generations into the cultural heart of Puerto Rican Chicago. Along the way you’ll see:
🎨 One-of-a-kind street art projects & murals (over 80!)
☕ Bustling coffee shops & Puerto Rican cafés
🏛️ Businesses named after Puerto Rican towns
🏘️ Façades inspired by old San Juan & Spanish Colonial architecture
⭐ The Paseo’s Walk of Fame, honoring outstanding Puerto Ricans🌳 Humboldt Park itself has been the symbolic nucleus of Puerto Rican Chicago since the 1960s. Here you’ll find La Casita de Don Pedro, historic Graystone homes, and three major public landmarks:
- The Boat House (designed by Schmidt, Garden & Martin)
- The Field House (recently renovated)
- The Historic Stables (now the National Museum of Puerto Rican Arts & Culture)
Named for German naturalist Alexander von Humboldt (1769–1859), the park was laid out in 1869 and is part of Chicago’s Boulevard Park System, a green necklace encircling the city. 🌿
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✅ Tour Highlights:
· 🇵🇷 Pass under the iconic Puerto Rican flags at Paseo Boricua
· 🎨 Explore murals & public art celebrating Puerto Rican pride
· 🏛️ Learn the history of Humboldt Park & monuments
· 🌳 Walk the formal garden & historic Boathouse
· 🏠 Visit La Casita de Don Pedro
🏤 Tour the National Museum of Puerto Rican Arts & Culture (former park stables!)📍 Tour Route & Logistics:
· Start: National Museum of Puerto Rican Arts & Culture, 3015 W. Division St.
· End: Ciclo Urbano, 2459 W. Division St. 🚲
o (about 6 blocks away – easy walk back to your car if you drove 🚗)
· Length: ~1.5 miles, outdoors 🌞🎒What to Bring:
· Water 💧
· Comfy walking shoes 👟
· Summer weather gear ☀️
· Facilities: Limited public restrooms—plan ahead 🚻
· $30 tour fee 💰🍽️ After the Tour:
We’ll grab a bite at one of the many fabulous Puerto Rican restaurants along Division Street! Options include:
· 🍴 Café Colao ☕
· 🍴 La Burqueña 🌮
· 🍴 Papa’s Cache Sabroso 🍗
· 🍴 Janellie’s Kitchen 🥘
· 🍴 Nellie’s Restaurant 🍳***
🚇 Transportation & Parking:
- CTA Trip Planner: https://www.transitchicago.com/planatrip/
- 🚇 Street parking available on Division, California, Western & side streets (watch for permit parking signs). 🅿️
***
📸 While not a strict photo walk, there will be plenty of opportunities to capture murals, monuments, and park views! 🌆
🙌 It’s a multi-meetup group event—please keep your RSVP updated and don’t be a no-show!
***
✨ Don’t miss this immersive walk through Chicago’s Puerto Rican heritage, culture & pride with an expert guide. 🇵🇷🌴🥁
- 🎵 Back in Time at the 28th Retro on Roscoe – KASHMIR, Dancing Queen & More! 🎸West Roscoe Street & North Damen Avenue, Chicago, IL
🎵 Back in Time at the 28th Retro on Roscoe – KASHMIR, Dancing Queen & More! 🎸
💃Retro on Roscoe – A Blast From The Past!
Ever wish you could go back in time? Here’s your chance! Referred to by Patch as a “Generation X haven”, the 28th annual Retro on Roscoe festival is your weekend destination for live music, vintage cars, artisans, and summer fun.
📅 Saturday, September 6, 2025
⏰ Tentative Meetup Time: 5:45 PM
📍 Roscoe Village, Chicago
💵 Suggested Donation: $15 (not mandatory – give what you can!)
***
🎶 Tentative Itinerary:
5:45 PM – Meet at the festival entrance
5:45–6:15 PM – Walk around festival: vendors, antique car show, food & drinks
6:00 PM – KASHMIR at West Stage (some will watch)
8:00 PM – Trippin Billies at Center Stage (optional split group)
8:30 PM – Dancing Queen at East Stage (most will watch)
***
🎵 Music Lineup (Saturday, Sept 6, 2025)
East Stage @ Damen- Noon – UpBeat Music & Arts Program
- 2:00 PM – Into The Heart: U2 Tribute
- 4:00 PM – Run Forrest Run
- 6:00 PM – Our Name is Jonas
- 8:30 PM – Dancing Queen: An ABBA Salute
Center Stage @ Hamilton
- 2:00 PM – Amanda Coppotelli
- 4:00 PM – 3 Martini Jeannie
- 6:00 PM – Funky Monks: RHCP Tribute
- 8:00 PM – Trippin Billies
West Stage @ Oakley Ave
- Noon – Aimont Moon
- 2:00 PM – Boots in Transit
- 4:00 PM – Whatever, Nevermind: Nirvana
- 6:00 PM – KASHMIR
- 8:00 PM – ROK Brigade
> Since two great bands play around 8 PM, we may split into small groups based on preference.
***
🪑 Seating
Limited seating available – bring a lawn chair or be ready to stand for most of the night.
🚗 Parking & Transit- Public Transit: Bus or train. Plan via CTA Trip Planner or Google Maps.
- Driving: Metered parking on Damen, Belmont, or further west on Roscoe. Limited side street parking. Best bet: SpotHero or ParkWhiz for safe, affordable parking.
***
🌟 Festival Highlights- Three music stages across a six-block stretch with throwbacks and oldies to keep you moving.
- Tree-lined streets full of artisans, antique vendors, and unique shops.
- Roscoe Village restaurants serving summer treats.
- Antique & Classic Car Show featuring 50+ cars and motorcycles.
More info: Retro on Roscoe
Band Links:***
⛔ No-Show Policy Reminder- 3 no-shows without updating RSVP = 3-month suspension from events.
- Cut-off to update RSVP is the start time; if you miss it, message the host directly.
- Always check in with the host upon arrival.
***
👉 Join us for a nostalgic night of music, dancing, vintage cars, and Roscoe Village charm!
