| Ride Across the Border Thru Houlton | 10-17-2021 | 29 | AB - Strenuous | |
| The Market Loop - Bloomington Bluffs | 10-16-2021 | 25 | B - Brisk | |
| Acapulco Ride (Stillwater) | 10-05-2021 | 24 | AB - Strenuous | |
| Tuesday Tuneup 2.0 | 10-12-2021 | 23 | AB - Strenuous | |
| The Market Loop – Ayd Mill and River to River Greenway | 10-03-2021 | 21 | B - Brisk | |
| Lift Bridge Brewery Ride | 10-07-2021 | 21 | AB - Strenuous | |
| Acapulco Ride (Stillwater) | 10-12-2021 | 21 | AB - Strenuous | |
| Spiral Brewery/Spring Lake Park Loop | 10-02-2021 | 20 | B - Brisk | |
| Rosetown American Legion Night Ride - Roseville | 10-11-2021 | 18 | NAB - Night Strenuous | |
| Outreach Ride: Mankato River Ramble | 10-10-2021 | 17 | Outreach | |
| Tuesday Tuneup 2.0 | 10-05-2021 | 17 | AB - Strenuous | |
| Wisconsin Hills Menomonie With Cookout | 10-10-2021 | 17 | B - Brisk | |
| Excelsior Expresso | 10-03-2021 | 17 | B - Brisk | |
| Station North Park to Hans Bakery and Rum River | 10-12-2021 | 15 | BC - Moderate | |
| WASHINGTON COUNTY TOUR | 10-09-2021 | 14 | BC - Moderate | |
| Fox and Shadow | 10-14-2021 | 14 | C - Relaxed | |
| Classic Redux | 10-07-2021 | 14 | B - Brisk | |
| Como-Minnehaha River Ride | 10-16-2021 | 14 | C - Relaxed | |
| PARK TO PARK | 10-08-2021 | 13 | BC - Moderate | |
| Groveland Tap Ride | 10-15-2021 | 13 | B - Brisk | |
| Champlin Mid Morning Ramble | 10-06-2021 | 13 | C - Relaxed | |
| Adventures from Invictus | 10-06-2021 | 13 | B - Brisk | |
| Cafe` Ride - Stillwater to Osceola Fall Colors | 10-09-2021 | 13 | AB - Strenuous | |
| Sakatah Singing Hills Trail | 10-09-2021 | 13 | C - Relaxed | |
| INTO WASHINGTON COUNTY | 10-12-2021 | 13 | BC - Moderate | |
| Friday Night Lights Oakdale | 10-08-2021 | 13 | NAB - Night Strenuous | |
| Groveland Tap Ride | 10-04-2021 | 13 | B - Brisk | |
| SUNDAY MORNING BRUNCH-ISH | 10-03-2021 | 12 | BC - Moderate | |
| Les Mis | 10-14-2021 | 12 | B - Brisk | |
| Mahtomedi Gravel Grinder Night Ride | 10-14-2021 | 12 | NB - Night Brisk | |
| Pre-Halloween Ride 29 Mile B | 10-10-2021 | 11 | B - Brisk | |
| Saturday Ride - TCBC Mountain Bike Weekend in Cable WI | 10-02-2021 | 11 | MBAB - Mountain Strenuous | |
| Pine Tree to Hugo | 10-07-2021 | 11 | C - Relaxed | |
| Como Dock & Paddle | 10-13-2021 | 11 | AB - Strenuous | |
| Wingnut | 10-09-2021 | 11 | AB - Strenuous | |
| Coon Rapids Dam to Bruegger's Bagels | 10-15-2021 | 10 | BC - Moderate | |
| FREE TUESDAY | 10-05-2021 | 10 | BC - Moderate | |
| Going Somewhere East 69 - Champlin | 10-04-2021 | 10 | AB - Strenuous | |
| Station North Park to Hans Bakery and Rum River | 10-05-2021 | 9 | BC - Moderate | |
| Coffee Corner Zimmerman - Champlin | 10-11-2021 | 9 | AB - Strenuous | |
| PARK TO PARK | 10-01-2021 | 9 | BC - Moderate | |
| Les Mis | 10-07-2021 | 9 | B - Brisk | |
| The Former TK's Coffee Ride | 10-14-2021 | 9 | B - Brisk | |
| Minnetonka Meander | 10-05-2021 | 9 | AB - Strenuous | |
| Roll to Independence | 10-03-2021 | 9 | AB - Strenuous | |
| St. Croix Crossing..."WI Backroads East 74" - Stillwater | 10-09-2021 | 9 | AB - Strenuous | |
| Windmill-Lake Elmo | 10-02-2021 | 8 | C - Relaxed | |
| Kodiak Kruze | 10-04-2021 | 8 | B - Brisk | |
| Sunday Spin Variant | 10-17-2021 | 8 | BC - Moderate | |
| Riding From St. Louis Park | 10-16-2021 | 8 | B - Brisk | |
| Gateway Express | 10-05-2021 | 8 | AB - Strenuous | |
| Friday Metric | 10-08-2021 | 8 | AB - Strenuous | |
| Lions Park to Sunrise Lake | 10-01-2021 | 7 | BC - Moderate | |
| Pink Express 10:30 Start | 10-11-2021 | 7 | B - Brisk | |
| Friday Ride - TCBC Mountain Bike Weekend in Cable WI | 10-01-2021 | 7 | MBAB - Mountain Strenuous | |
| Wisconsin Hills - River Falls October Loop | 10-17-2021 | 7 | AB - Strenuous | |
| 9 Mile Creek Pizza Ride | 10-07-2021 | 7 | BC - Moderate | |
| Cafe` Ride / Cruzin The Crow | 10-02-2021 | 7 | AB - Strenuous | |
| PARK TO PARK | 10-15-2021 | 7 | BC - Moderate | |
| Early Fall Colors - Scandia | 10-02-2021 | 7 | AB - Strenuous | |
| Friday Metric | 10-01-2021 | 6 | AB - Strenuous | |
| Little Big Marine | 10-17-2021 | 6 | C - Relaxed | |
| Sunday Spin | 10-10-2021 | 6 | BC - Moderate | |
| Hugo Moose Adventure 66 | 10-06-2021 | 6 | AB - Strenuous | |
| The Triangle | 10-05-2021 | 6 | C - Relaxed | |
| Lions Park to Sunrise Lake | 10-08-2021 | 6 | BC - Moderate | |
| North by North St Paul | 10-04-2021 | 6 | C - Relaxed | |
| Bru House Coffee North - Champlin | 10-10-2021 | 5 | AB - Strenuous | |
| PINE TREE TO HUGO | 10-07-2021 | 5 | BC - Moderate | |
| Excelsior Expresso | 10-17-2021 | 5 | B - Brisk | |
| Gateway Express | 10-12-2021 | 5 | AB - Strenuous | |
| Free and Easier Tuesday | 10-05-2021 | 5 | C - Relaxed | |
| Alpine Park to Twin Lakes | 10-11-2021 | 4 | BC - Moderate | |
| Original North Hennepin Ride | 10-03-2021 | 4 | BC - Moderate | |
| Wisconsin Hills - The Ellsworth Express 57 | 10-03-2021 | 4 | AB - Strenuous | |
| Kodiak Kruze | 10-11-2021 | 4 | B - Brisk | |
| North by North St Paul | 10-11-2021 | 4 | C - Relaxed | |
| Station North Park to Rum River Park | 10-04-2021 | 4 | BC - Moderate | |
| Pine Tree to Marine on St. Croix | 10-06-2021 | 3 | B - Brisk | |
| Wake Up and Ride! (St Louis Park) | 10-13-2021 | 3 | BC - Moderate | |
| Hugo All - Roads 54 | 10-07-2021 | 2 | AB - Strenuous | |
| Sunrise Solitude | 10-10-2021 | 2 | AB - Strenuous | |
| Wake Up and Ride! (St Louis Park) | 10-06-2021 | 2 | BC - Moderate | |
| Sand Plains Elements & Minerals - Champlin | 10-14-2021 | 2 | AB - Strenuous | |
| Bonus Metric (St Louis Park) | 10-12-2021 | 2 | AB - Strenuous | |