Thanks Joshua!
I have used Shape2SQL but it doesn't seem to like shapefiles with too many features. The file I am trying to convert to SQL Server has around 40,000 features and when I try to use Shape2SQL, it seems to finish but the table is nowhere to be found in the SQL database.
I should also note that I do not have administrator rights on my machine nor is my SQL Server database enterprise enabled.
So regarding the WKT, could I calculate the WKT for each feature in a DBF table instead of a feature to get around the shapefile limit?
Thanks!