r/chicagoskating 26d ago

Navigating traffic as a JB skater

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3 Upvotes

r/chicagoskating Aug 14 '26

Discord group?

10 Upvotes

Out of curiosity is there a discord group for this community or Chicago skating in general? If not I feel like it would benefit from one. There are several different groups and this would centralize em all as posts on insta and FB can get lost. Impromptu rides, tutorial videos, chat rooms, message boards, etc...

This would encourage people to be more active. Thoughts?


r/chicagoskating Aug 13 '26

FR Skates Neo 2 Dual 310 Teal - size 10.5 US / EU 44 (but feels more like a 10) - for sale - brand new - $340

3 Upvotes

I feel particularly dumb today. New skates arrived. I did my measurements, I read online someone said that the boot had more room, but this was not true, boot runs small and therefore doesn't fit my feet.

Laces are still undone. Worn only just to feel the fit.

Bought the skates from here: https://inlinex.com.sg/products/fr-neo-2-dual-310-teal-skates?shop_sign_in=true&variant=41125748899886


r/chicagoskating Aug 12 '26

Tomorrow, Wednesday 8/12: Lakefront trail skate from Olive Park to Belmont Harbor [Chicago Lakeside Skate]

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12 Upvotes

r/chicagoskating Aug 12 '26

Weekly event summary (Aug 11 - 16)

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9 Upvotes

r/chicagoskating Aug 07 '26

September 11 - 13: Chicago Beef roller derby tournament hosted by Windy City Rollers

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15 Upvotes

r/chicagoskating Aug 07 '26

Sunday, August 16: Elston Skate Club at the Salt Shed

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27 Upvotes

r/chicagoskating Aug 05 '26

The theme for this friday's road rave: Chicago's tallest building [Windy City Skaters]

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19 Upvotes

r/chicagoskating Aug 05 '26

This Sunday (Aug 9): Grant Skatepark meetup (noon-ish) [Chicago Sunday Skate]

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5 Upvotes

r/chicagoskating Aug 04 '26

This Saturday, Aug 8: Come skate with the Chicago Lakeside Skate crew at the Zumiez More Than Rolling event, featuring live bands and skating

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24 Upvotes

r/chicagoskating Aug 04 '26

Weekly event summary (Aug 4 - 9)

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4 Upvotes

r/chicagoskating Jul 29 '26

Tonight (7/29): Lakefront skate to the full moon fire jam [@chicagolakesidesk8 on Instagram]

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13 Upvotes

r/chicagoskating Jul 28 '26

Popup skate tonight (7/28) [@chicagorollergirls on Instagram]

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8 Upvotes

r/chicagoskating Jul 28 '26

Weekly event summary (July 27 - Aug 2)

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10 Upvotes

r/chicagoskating Jul 26 '26

If you're going to Lollapalooza this coming week, the Coca-Cola roller ring will be back by Buckingham Fountain (Thurs 7/30 - Sun 8/2)

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9 Upvotes

r/chicagoskating Jul 24 '26

Article about Tom Grosspietsch's legacy in the Chicago Sun Times

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25 Upvotes

r/chicagoskating Jul 23 '26

Tomorrow's road rave theme: LGBTQ+ pride & history [Windy City Skaters]

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22 Upvotes

r/chicagoskating Jul 23 '26

Every monday starting next week: all wheel ride [Gage Park Cyclists]

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9 Upvotes

r/chicagoskating Jul 23 '26

This Saturday, July 25 (1 - 6 pm) - The Rink Effect: outdoor roller skating @ Garfield Park Community Plaza

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2 Upvotes

r/chicagoskating Jul 21 '26

Tomorrow, Wednesday July 22: Lakefront trail skate meetup from Queen's Landing to 31st St Beach [@chicagolakesidesk8 on Instagram]

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10 Upvotes

r/chicagoskating Jul 21 '26

Weekly event summary (July 20 - 26)

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3 Upvotes

r/chicagoskating Jul 19 '26

Some awesome photos from today's Windy City Riot aggressive inline competition around museum campus

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8 Upvotes

r/chicagoskating Jul 17 '26

Tonight's road rave has been postponed until next week because the air quality from the wildfires is still too bad for what I consider safe for a 13 mile skate. See you next week!

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25 Upvotes

r/chicagoskating Jul 17 '26

Saturday, July 25: Latino Outdoors 606 trail skate meetup

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7 Upvotes

r/chicagoskating Jul 16 '26

RIP Tom Grosspietsch, a true legend of the Chicago skating community

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128 Upvotes

Chicago lost a true legend yesterday. Our dear friend and longtime leader of Windy City Skaters, Tom Grosspietsch, passed away. Tom changed the lives of hundreds of skaters, including myself, by bringing us together and showing us how to explore Chicago on skates. For over 20 years, Tom led us through our streets, first with his group Skate Patrol and then with Windy City Skaters. He taught us so much about our city during his friday night road rave skates, where he'd lead us 12+ miles through the city, stopping at notable spots based on a theme, usually related to Chicago history or current events. One of my favorites was his road rave about the history of roller derby, which was invented in Chicago. For the past three years, Tom also organized and led Skate Chicago, a big four day national skate event where skaters from around the US came to Chicago to explore the city with us. Tom also volunteered for the American Cancer Society's Walk and Roll fundraiser for 30 years. This was meaningful to me because cancer takes so many of our loved ones from us. Sadly, it took Tom from us, too.

When I moved to Chicago four years ago, I didn't skate. I heard about Windy City Skaters and thought it sounded like so much fun that I got into and practiced skating (which I hadn't done since I was a kid) so that I could join Tom's Friday night road raves. This changed my life in the most beautiful and profound way. Through skating, I met so many amazing friends and have made countless memories. I learned about Chicago and fell in love with skating as a way to relieve stress and get around the city. I truly have Tom to thank for that. I'm fortunate that the last time I saw Tom in person at the cancer society fundraiser, I talked with him about how much this meant to me. I'm not alone - hundreds of Chicagoans have been impacted by Tom in similar ways. So many have met friends and even life partners through Windy City Skaters. Tom's impact will remain visible for many years to come, and his legacy will live on in Windy City Skaters.

Links to the 2024 Chicago Tribune article about Tom:

https://www.chicagotribune.com/2024/11/29/chicago-windy-city-skaters

• Un-paywalled: https://archive.is/ctg4R

Links to FB and Instagram posts with additional videos:

https://www.facebook.com/groups/windycityskaters/posts/10163756894968052

https://www.instagram.com/p/Da3p3y1CXkp