The incident has taken place between the Tesco Express store and the Central store and is leading to significant delays in the area.
2 appliances from the Isle of Wight Fire and Rescue Service – 1 from Newport and 1 from Ryde – are on scene and firefighters are assisting paramedic colleagues.
Emergency services were alerted to the incident at just before 18:20.
The road is closed in both directions with local diversions in place via Rectory Drive and Mary Rose Avenue.
UPDATE @ 18:53 – 1 person has been conveyed to hospital having been assisted from 1 of the 3 vehicles involved in the crash.
Significant damage has been sustained to at least 2 cars, a Citoren C3 and a Ford KA, the latter of which has collided into a wall.
Fire crews and paramedics are now standing down from the incident but the road remains closed whilst Police arrange recovery of the vehicles.
UPDATE @ 21:50 – Wootton High Street has now re-opened in both directions.