| | Organization Name(s) | Located In |
 | R Family Farm | Cookstown |
| Rainbow Valley Riding Center | Phelpston |
| Rainbow View Farm | Springwater |
| Rainbows For All Children Canada, Barrie Collier Street United Church Programs | Barrie |
| Rainbows For All Children Canada, Canadian National Office | Barrie |
| Rainbows For All Children Canada, Silver Linings Program | Barrie |
| Rainbows for All Children Canada. Rainbows, Spectrum, Prism Programs. North Simcoe Rainbows | Midland |
| RAW CrossFit | Penetanguishene |
| Ray's Driving School. Barrie | Barrie |
| Ray's Driving School. Midland | Midland |
| Real Canadian Superstore, Cooking Classes | Midland |
| Real Canadian Superstore Community Room. Midland, Meeting Facilities | Midland |
| Real Canadian Superstore Pharmacy. Midland | Midland |
| Recreational Aircraft Association. Midland/Huronia Chapter | Tiny |
| Recreational Mixed Slo-Pitch. Hillsdale | Hillsdale |
| | Red Hat Society | Simcoe County |
| Redgrift (Dr. James) | Midland |
| Reid (Dr Linda) | Midland |
| | Rena K. Mobile Hair Services | Simcoe North |
| Responsible Gaming Resource Centre | Innisfil |
| Retire-At-Home Services | Simcoe County |
| | Retired Teachers of Ontario, District 17 | Barrie |
| Revera Home Health, Barrie Office | Barrie |
| River of Life Pentecostal Church. Midland | Midland |
| RJ Motosport Park | Midhurst |
| RJC Connections Transportation Service | Barrie |
| Road to Recovery Addiction Clinic, Midland Location | Midland |
| Roberta Place | Barrie |
| Robertson Denture Clinic. Midland | Midland |
| Rogers Cable Inc. Midland Location, Rogers TV | Midland |
| Rogers TV | Barrie |
| | Rotary Club of Midland | Midland |
| | Rotary Club of Penetanguishene | Penetanguishene |
| Rounds Ranch | Springwater |
| Royal Canadian Air Cadets. Midland Squadron 724 | Midland |
| Royal Canadian Legion, Barrie Branch 147 | Barrie |
| Royal Canadian Legion Branch 80, Ken Snider Memorial Museum | Midland |
| Royal Canadian Legion. Elmvale Branch 262 | Elmvale |
| Royal Canadian Legion. Elmvale Branch 262, Ladies Auxiliary | Elmvale |
| Royal Canadian Legion. Elmvale Branch 262, Meeting Facilities | Elmvale |
| Royal Canadian Legion. Elmvale Branch 262, Operation: Leave The Streets Behind - Homeless Veterans Assistance | Elmvale |
| Royal Canadian Legion. Midland Branch 80 | Midland |
| Royal Canadian Legion. Midland Branch 80, Ladies' Auxiliary | Midland |
| Royal Canadian Legion. Midland Branch 80, Meeting Facilities | Midland |
| Royal Canadian Legion. Midland Branch 80, Operation: Leave The Streets Behind - Homeless Veterans Assistance | Midland |
| Royal Canadian Legion. Penetanguishene Branch 68 | Penetanguishene |
| Royal Canadian Legion. Penetanguishene Branch 68, Hall Rental | Penetanguishene |
| Royal Canadian Legion. Penetanguishene Branch 68, Ladies Auxiliary | Penetanguishene |
| Royal Canadian Legion. Penetanguishene Branch 68, Operation: Leave The Streets Behind - Homeless Veterans Assistance | Penetanguishene |
| Royal Canadian Legion. Port McNicoll Branch 545 | Port McNicoll |
| Royal Canadian Legion. Port McNicoll Branch 545, Ladies Auxiliary | Port McNicoll |
| Royal Canadian Legion. Port McNicoll Branch 545, Meeting Facilities | Port McNicoll |
| Royal Canadian Legion. Port McNicoll Branch 545, Operation: Leave The Streets Behind - Homeless Veterans Assistance | Port McNicoll |
| Royal Canadian Legion. Victoria Harbour Branch 523 | Victoria Harbour |
| Royal Canadian Legion. Victoria Harbour Branch 523, Ladies Auxiliary | Victoria Harbour |
| Royal Canadian Legion. Victoria Harbour Branch 523, Meeting Facilities | Victoria Harbour |
| Royal Canadian Legion. Waubaushene Branch 316 | Waubaushene |
| Royal Canadian Legion. Waubaushene Branch 316, Ladies Auxiliary | Waubaushene |
| Royal Canadian Sea Cadet Corps (286) Trillium. Midland | Midland |
| Royal Canadian Sea Cadet Corps 53 Barrie | Barrie |
| Royal College of Dental Surgeons of Ontario | Toronto |
| Royal Victoria Regional Health Centre | Barrie |
| Royal Victoria Regional Health Centre, Adult Outpatient Services, Hand/Plastics Program | Barrie |
| Royal Victoria Regional Health Centre, Adult Outpatient Services, Physiotherapy Services | Barrie |
| Royal Victoria Regional Health Centre, Adult Outpatient Services, Rehabilitation Day Hospital | Barrie |
| Royal Victoria Regional Health Centre, Adult Outpatient Services, Swallowing Disorders Clinic | Barrie |
| Royal Victoria Regional Health Centre, Breast Imaging | Barrie |
| Royal Victoria Regional Health Centre, Cardio-Respiratory Services | Barrie |
| Royal Victoria Regional Health Centre, Dialysis/Kidney Care Clinic | Barrie |
| Royal Victoria Regional Health Centre, Health Library | Barrie |
| Royal Victoria Regional Health Centre, Maternal Child Program, Birthing Unit, Labour and Birthing Classes | Barrie |
| Royal Victoria Regional Health Centre, Maternal, Child and Youth Program, Child and Youth Outpatient Services, Children's Development Services, Occupational Therapy | Barrie |
| Royal Victoria Regional Health Centre, Maternal, Child and Youth Program, Child and Youth Outpatient Services, Children's Development Services, Simcoe County Preschool Speech and Language Program. Midland Location | Midland |
| Royal Victoria Regional Health Centre, Maternal, Child and Youth Program, Child and Youth Outpatient Services, Children's Development Services, Simcoe Muskoka Parry Sound Blind Low Vision Early Intervention Program | Barrie |
| Royal Victoria Regional Health Centre, Maternal, Child and Youth Program, Child and Youth Outpatient Services, Children's Development Services, Simcoe Muskoka Parry Sound Infant Hearing Program | Barrie |
| Royal Victoria Regional Health Centre, Maternal, Child and Youth Program, Child and Youth Outpatient Services, Hearing Health Services, Audiology and Hearing Instrument Dispensing | Barrie |
| Royal Victoria Regional Health Centre, Mental Health and Addiction Program, Addiction Services | Barrie |
| Royal Victoria Regional Health Centre, Mental Health and Addiction Program, Community Treatment Order Coordination Service | Barrie |
| Royal Victoria Regional Health Centre, Mental Health and Addiction Program, Crisis Intervention Services | Barrie |
| Royal Victoria Regional Health Centre, Mental Health and Addiction Program, Medication Clinic | Barrie |
| Royal Victoria Regional Health Centre, Mental Health and Addiction Program, Mental Health Outpatient Services | Barrie |
| Royal Victoria Regional Health Centre, Outpatient Rehabilitation Services, Cardiac Rehabilitation Program | Barrie |
| Royal Victoria Regional Health Centre, Patient Food Services | Barrie |
| Royal Victoria Regional Health Centre, Patient Representative Office | Barrie |
| | Royal Victoria Regional Health Centre, Simcoe Muskoka Regional Cancer Program, iQuit contest | Barrie |
| Royal Victoria Regional Health Centre, Simcoe Muskoka Regional Cancer Program, Simcoe Muskoka Regional Cancer Centre | Barrie |
| | Ruggers United Gathering | Barrie |
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