It’s a fair question, and the answer is yes: you can over-trim a hedge. Cutting too hard or too often can leave a hedge stressed, patchy and slow to recover.
The risks of over-trimming
Cutting back into old, leafless wood — especially on conifers like many Wellington hedges — can leave permanent bare patches, because that growth won’t always regenerate. Over-frequent hard cuts also stress the plant.
How to trim safely
Stick to trimming the current season’s growth and avoid cutting deep into old wood. Regular light trims keep a hedge dense and healthy far better than occasional severe ones.
Renovating an overgrown hedge
If a hedge has become too big, it can sometimes be renovated hard over a couple of seasons — but this depends heavily on the species. Get advice first so you don’t lose the hedge.

