He is best known for his role in developing a public transport system in Christchurch and as a key player in the establishment of the Royal New Zealand Air Force.

[2] Together with his brother, William Arthur Wigram, Henry bought a malthouse and brickworks business in the Heathcote Valley between Christchurch and Lyttelton.

His prominence in business led to Wigram being invited to chair the committee for the Canterbury Jubilee celebration in 1900, and he remained heavily involved in public affairs for the next thirty years.

In order to facilitate planning and the development of infrastructure, Wigram campaigned for a reduction in the eleven separate boroughs that made up Greater Christchurch, and was successful in getting Linwood, St Albans and Sydenham to amalgamate with the city.

Unsuccessful at persuading the New Zealand Government to become involved in aviation, he formed a private flying school in Christchurch in 1915.