Chicago
Group
Rides
Looking for a group ride to join in Chicago? You're in the right place! Below, find a list of regularly scheduled open group rides that take place each day of the week. You'll also find details of where the rides leave from, pacing, and distance.
This list is maintained by Half Acre Cycling. We recommend checking with the ride hosts via their social media pages or websites to confirm details before joining.
Helmets required • No Tri-Bars • Bring flat kit • Bring lights for evening rides
Monday Rides
Mondays; 6:00 pm
Start LocationDunkin Donuts at Lincoln and California
Pace and Distance20-25 mph; 30-35 miles
RouteRide WebsiteNotesemphasis on smooth riding techniques, paceline etiquette, practice sprints, and building confidence on the open road
Updated on 6/13/2023
Mondays; 6:00 pm
Start LocationSpecialized Chicago Lincoln Park
Pace and DistanceDistance may change, so please check the RIDE app to see what's on the menu
Ride WebsiteNotesJoin us at Specialized Lincoln Park for our weekly Monday night ride! Distance may change, so please check the RIDE app to see what's on the menu, to sign a ride waiver (if you've not already signed), and to stay up to date on Specialized Rides and Events.
Updated on 6/13/2023
Mondays, 6:15 pm
Start LocationPickwick Theater
Pace and Distance16 miles with cruising speeds capped at 18mph and 14mph for the two groups
Ride WebsiteNotesMonday Social Rides depart summer evenings at 6:15 pm in front of the Park Ridge library, 20 S Prospect Ave. A 1-hour loop into Glenview. Two speed options. Newcomer? Start here! Rides often end at Beer on the Wall or Harp & Fiddle (both on Main St.) for those who wish to grab dinner or a drink. Rides run June 3 to Sept 9 (first Monday after Memorial Day to the first one after Labor Day). For September rides, bring front and rear lights.
Updated on 12/29/2025
Tuesday Rides
Tuesday, 6pm meetup, 6:30 rollout
Start LocationPace and Distancecasual pace 10-20 miles
NotesFrom the instagram post announcement: "The whole idea behind this gorup ride is to get out and enjoy ourselves while building a positive and inviting community around cycling!"
Updated on 4/9/2025
Tuesday, Meet at 6pm - roll out as soon as we get the shop closed up
Start LocationPace and DistancePace depending on who shows up typically anywhere from 16 to 18 mph. Distance 25-40miles, usually around 30/35
NotesNo drop, we’ll wait. Begins and ends with daylight savings time change.
Updated on 8/18/2023
Tuesdays, 6:00 pm
Start LocationPace and Distance16 mph; 35 miles
Ride WebsiteUpdated on 4/9/2025
Tuesdays, 5:30 am
Start LocationLocation may vary so check the calendar. Normally will be at Hexe Coffee.
Pace and DistanceRoute is ride leader's choice. Check the calendar for details on pace, route, and distance
Ride WebsiteNotesFrom the SMC website: "summers only . . . we go up to Tower and back . . . some of us need to be to work by 8!"
Updated on 4/9/2025
Tuesdays, 7:30pm (year round!)
Start LocationMeets in Logan Square. Message on IG for location details
Pace and Distance13-20mph rolling speed (14ish full average), 30-50 mi during the summer
Ride WebsiteNotesno-drop ride with a mix of pavement, dirt, and gravel.
Updated on 6/13/2023
Tuesdays, 5:30pm
Start Location933 Skokie Blvd, Northbrook, IL 60062
Pace and DistanceExpect a 1.5 hour 36 mile road ride. 2 groups (avg. speed) Group A 26mph+ Group B 21mph+
RouteUpdated on 4/9/2025
Tuesdays, 5pm
Start LocationOak Park
Ride WebsiteNotesTuesdays & Thursdays around 5pm. Drinks/socializing after Thurs night ride
Updated on 4/9/2025
Wednesday Rides
Wednesdays, 6:00 pm
Start LocationWinnemac Park Parking lot, Winnemac and Damen
Pace and Distance16-18 mph; 20 miles
Ride WebsiteNotesPlease RSVP before showing up!
Updated on 4/9/2025
First Wednesday of each month at 6pm
Start LocationTrek Wicker Park
Ride WebsiteNotesSupporting BIPOC-owned restaurants and providing a safe space for Femme, Trans, Women, and Non-Binary cyclists of color
Updated on 6/18/2024
Wednesdays, 5:30 pm
Start LocationPace and Distance22-32 mph; 35-40 miles
RouteRide WebsiteNotesGreat race simulation, advanced riders
Updated on 6/13/2023
Wednesdays, 6pm
Start LocationPace and Distance20-25 mph, drop ride to Highland Park
RouteUpdated on 5/1/2024
Wednesdays, 5:30pm
Start Location8201 N. Caldwell Ave., Morton Grove, IL 60053
Pace and DistanceExpect a 1.5 hour road ride with a 20+ mph average speed.
NotesWe will keep the group together. Look for bikes and red and white jerseys. There will be a mid ride stop at the Highland Park train station.
Updated on 4/9/2025
Wednesdays, 7am
Start LocationJohn's place - corner of Roscoe & Hamilton
Pace and Distance16-18mph No drop. About 15-20 mi.
NotesIntermediate riders who want a casual, friendly pre-work warm-up ride, but nothing super hardcore and not competitive. No predefined route, and will pick river, lake, etc depending on what the group feels like that day. Anyone who wants to join can email [email protected] or message on WhatsApp via +1-312-888-6360
Updated on 8/7/2024
Thursday Rides
Various Thursdays, 6:30pm to 7:30pm
Start LocationPace and Distance8-10miles, 12-14mph
Ride WebsiteNotesRoutes varry, but they always end back at BFF Bikes. Beginner friendly, no previous group experience required.
Updated on 4/9/2025
Thursdays, 5:30 pm starting in April
Start Location5440 N. Clark Street in the Walgreens parking lot in Andersonville
Pace and DistanceDepending who shows; +/-30 miles
RouteRide WebsiteNotesNo drop, Lights required, Ride ends at Spiteful Brewery 2024 W. Balmoral Ave, Chicago
Updated on 3/3/2024
Every third Thursdays; 6:00 pm
Start LocationThe Bike Lane - 2130 N Milwaukee
Pace and Distancechill pace; less than 20 miles
Ride WebsiteNotesCheck The Bike Lane's Instagram/stories for updates
Updated on 9/14/2022
Thursdays, 8pm (see notes)
Start LocationMcCormick Place
Pace and Distancetypically about 10 miles
Ride WebsiteNotesStarting in May, typically Thursday nights at 8pm with some weeks switch to Wednesdays. And some special rides on Saturdays, as well as the Juneteenth ride. Pace at the front is a little fast, but it's open to all paces/skillsets. For more information, visit the website or @streetscalling.bc on Instagram.
Updated on 4/3/2025
Tuesdays, 5pm
Start LocationOak Park
Ride WebsiteNotesTuesdays & Thursdays around 5pm. Drinks/socializing after Thurs night ride
Updated on 4/9/2025
Friday Rides
Friday, 6:30am
Start LocationCheck Instagram
Pace and Distanceaverage pace 16-18mph
Ride WebsiteNotesMeetup location and route change week-to-week. Check Instagram for updates. Please RSVP with the link in our Instagram bio.
Updated on 6/12/2024
Fridays, 6:30am
Start LocationPace and Distance16-18 mph, sprint on the south end of LFT
Updated on 4/9/2025
Saturday Rides
Saturdays, 7:15 for a 7:30 roll out
Start LocationSweetwaters Coffee and Tea, 1457 N Halsted St B105, Chicago, IL 60642
Pace and Distance~45 miles, 17mph - 20mph rolling, paceline practice included, no drop
NotesStart May 26. Open to BIPOC only. Alternates between Grindhouse and Highland Park. With a coffee stop at the midpoint always! One longer adventure SMR once a month. Check social media for specifics.
Updated on 4/9/2025
Saturdays 7:30am
Start LocationPace and Distance24-34 mph; 50-80 miles
Updated on 4/9/2025
Saturdays, 7:00am starting in April (8am in March)
Start Location5440 N. Clark Street in the Walgreens parking lot in Andersonville
Pace and DistanceRolling pace of 20-22+ mph; 55+ Miles that Vary each week
Ride WebsiteNotesVaries every week join our discord for more info on Saturday rides. Typically stays as one group but may separate into more groups depending on turn out and experience of riders. One stop for midway that can be at a coffee stop, gas station or park depending the route. At end of ride group might end up going to Spiteful for beers.
Updated on 4/24/2024
Saturdays 8am
Start LocationPace and Distance18-20 mph no drop
RouteUpdated on 6/13/2023
Saturdays, 8:00am
Start LocationPace and Distance18-22 mph to Highland Park (with optional extensions)
Ride WebsiteNotesFrom the SMC website: "Great ride for a beginner, we will make sure you get up to Highland Park with us."
Updated on 4/9/2025
usually first Saturday of the month (check social media for details)
Start LocationLocation varies (check social media for details)
Pace and Distancedepends on who shows up, beginner friendly
Ride WebsiteNotesvery beginner friendly
Updated on 6/13/2023
Saturdays, 7:00am (summer) Offseason starts at 8am. Goes year round!
Start LocationNorthwest corner of Wicker Park, south of the intersection of North/Damen/Milwaukee
Pace and Distance18-22 mph; 47 miles
Ride WebsiteNotesSecond meeting point at Pratt and Ridge at 7:30. no drop up to HP, drop on the way back. May-Oct start 7:00 AM, Nov-Apr start 8:00 AM. Thorough details are available on the ride page, check it out!
Updated on 4/9/2025
Saturdays, 9am
Start LocationAddison intersection of the Lake Path
Pace and Distance12-15mph, 27 Miles
Ride WebsiteNotesWindy City Cycling. A LGBTQ+ cycling group in Chicago.Casual lakefront bike ride to Hyde Park
Updated on 8/16/2023
Saturdays, 7:30am
Start LocationPace and Distance18-19mph, 54 miles
NotesIntermediate pace with opportunities along the way and back, to bring up the pace a little bit. After these sections we will give others a chance to catch back on to the group as this is a 'no-drop' ride. Group riding experience is highly recommended.
Updated on 4/9/2025
Saturdays, 10am
Start LocationLake Front Trail at Ohio Beach
Pace and DistanceCasual spin, 1 hour
Ride WebsiteNotesThe vibe/pace is very chill coffee ride and the club is social centric. Open to anyone.
Updated on 4/9/2025
Saturdays, 9:00am
Start LocationDam No. 1 Woods East, 621 W Dundee Rd, Wheeling, IL 60090, 42.136019, -87.900645
Pace and DistanceExpect a 2.5 hour ROAD Ride. 46 to 50 mile ride with a 19+ mph average speed.
NotesThis is a tempo ride and both routes feature a coffee stop and regroup areas, we will do our best to keep the group together. We alternate routes weekly. We do a route to Tala Coffee Roasters and a hilly route that heads west to Barrington.
Updated on 5/28/2024
Saturdays, departure time TBD
Start LocationPickwick Theatre
Ride WebsiteNotesGroup rides are year round, weather permitting, with start times moving based on sunrise. Once we get to the colder months, the best way to be notified is to sign up on our listserv. We run A and B rides year around and C rides between April and October. A/B rides are usually 55 miles with a turnaround option usually 15-20 miles in. C rides are generally 20-35 miles. A/B rides are generally 18-22 mph. B is no drop. C rides are 15-16 mph, no drop.
Updated on 12/29/2024
Sunday Rides
Various Sundays, 8am to 10am
Start LocationPace and Distance12-18miles, 12-14mph pace
Ride WebsiteNotesNo drop and no previous group ride experience necessary
Updated on 4/9/2025
Various Sundays, 8am to 10:30am
Start LocationPace and Distance16-18 mph, 30-50 miles
Ride WebsiteNotesplease check the calendar on BFF's site to confirm the ride is being held
Updated on 4/9/2025
Sundays, 7:30am summer (8:30am winter)
Start Location5440 N. Clark Street in the Walgreens parking lot in Andersonville
Pace and DistanceGroup A: 25- 30 mph rolling speeds (DROP RIDE with no re-groups); 45 miles
RouteRide WebsiteNotesDrop ride, after-ride coffee at Misericordia's Hearts & Flour Bakery and Cafe
Updated on 4/9/2025
Sundays, 7:30am summer (8:30am winter)
Start Location5440 N. Clark Street in the Walgreens parking lot in Andersonville
Pace and Distance45 miles; Group B will split into B+ and B depending on number of riders that show up. Group B+: 20 - 25mph rolling speeds (Drop Ride). Group B: 17-22mph rolling speeds (No-Drop Ride and Sweeper)
RouteRide WebsiteNotesBeginners welcome! No drop, after-ride coffee at Misericordia's Hearts & Flour Bakery and Cafe
Updated on 4/9/2025
Various Sundays, 9:30am
Start LocationPace and Distance18-20 mph, no drop
Ride WebsiteNotesCheck social media or Discord to confirm
Updated on 4/9/2025
Sundays, 8am
Start LocationPace and Distance18-20mph, 30 miles going south
Updated on 4/9/2025
Sundays, 8:00 am
Start LocationPace and Distancefaster than Saturdays, route is ride leader's choice
Ride WebsiteNotesFrom the SMC website: "This is a ride leader’s choice ride. Normally this ride requires group riding experience. May be a drop ride and faster pace, check the calendar for details. Route varies week to week so always meet at Clybourn and Damen!"
Updated on 4/9/2025
Sundays, 8am
Start LocationPace and Distance18-20 mph, 47 Miles
Ride WebsiteNotesWindy City Cycling. A LGBTQ+ cycling group in Chicago.
Updated on 8/16/2023
Sundays, 9am
Start Location8201 N. Caldwell Ave., Morton Grove, IL 60053
Pace and DistanceExpect about a 2.5 hour ride. 42 miles with 3 pace groups. Group A is a 25+ mph avg speed - Drop Ride Group B 20+ mph avg speed Group C 17+ mph avg speed
RouteNotesThere is a stop in Fort Sheridan and an optional coffee stop at Plaza de Lago
Updated on 5/28/2024
Saturdays, departure time TBD
Start LocationPickwick Theatre
Ride WebsiteNotesGroup rides are year round, weather permitting, with start times moving based on sunrise. Once we get to the colder months, the best way to be notified is to sign up on our listserv. We run A and B rides year around and C rides between April and October. A/B rides are usually 55 miles with a turnaround option usually 15-20 miles in. C rides are generally 20-35 miles.
Updated on 12/29/2024
Other Rides
Tuesdays when the Sox play at home
Start LocationDaley Plaza (or hop on along the Lakefront Trail)
Ride WebsiteNotesChicago Bike Sox is the bike community's summer pastime. They bike to the ballpark and tailgate at the bike racks between gates 2 & 3. Roll from Daley Plaza, use the ride tracker to hop on along the route, or make your own way and meet up at the racks for the tailgate. The ride is 7 miles at a chill, inclusive pace. Everyone is welcome!
Updated on 4/9/2025
Check @dykesonbicycles on Instagram for more information about the rides.
Updated on 4/9/2025
Pace varies according to ride and day.
Ride WebsiteNotesChain Reaction Cycling Club (CRCC) a south side based group focused on building better riders. Check Instagram for more information on public rides.
Updated on 4/9/2025
Last Friday of every month, 6pm
Start LocationDaley Plaza
Ride WebsiteNotesCritical Mass is a large group bicycling event, gathering in Chicago the last Friday of every month for decades. Leaves Daley Plaza downtown around 6pm.
Updated on 4/9/2025
First Saturday of the month
Ride WebsiteNotesA safe space for women, femme, non-binary and trans Chicagoans to ride bikes together. No-drop social rides every 1st Saturday of the month.
Updated on 4/9/2025
Check Strava for rides that are open to non-members
Start LocationRapha Chicago
Ride WebsiteUpdated on 4/9/2025
Check @indigocyclingchicago on Instagram for details
Updated on 9/9/2024
The Major Taylor Cycling Club Chicago (MTC3) is dedicated to promoting fitness, fellowship and fun while fostering a sense of community among cyclists, and honoring the legacy of Marshall “Major” Taylor. There is a ride for every speed nearly every day of the cycling season, with most rides starting in the City of Chicago or throughout the south suburbs. Faster days are Tuesday and Thursday; nights starting at the Bartel Grasslands or mornings at E 87th & South DuSable Lake Shore Drive. Check the full calendar for times, paces and ride leader contact info.
Updated on 4/9/2025
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