The flame crossed the border just after 10:30 BST on its journey from and was greeted by enthusiastic specatators in Monmouth.
In Abergavenny the weight of numbers in the narrow streets forced the vehicle convoy to take a brief detour, although the torchbearer ran the planned route.
Doctor Who star Matt Smith will carry the torch in Cardiff on Saturday.
The flame will pass through more than 80 towns, villages and cities in Wales from 25-30 May.
The first bearer on Welsh soil was Gareth John MBE, chairman of Disability Sport Wales.
He then passed the flame to Robyn Tyler, 21, who has lost more than six stones in the past year. She said she was "overwhelmed" to be carrying the flame.
"Seeing the torch travel through Monmouth means a lot to all of us here," she said. "Despite being a small town on the Welsh border, we feel so much a part of the bigger London 2012 picture."Later, the torch travelled through the highest town in Wales, Brynmawr, and at lunchtime it visits Big Pit in Blaenavon.
It closed as a working mine in the 1980s but reopened in 2004 after being bought by the National Museum for Wales.
Visitors are taken 100m (300ft) underground using the pit shaft to reach the coalface and are shown around by former miners.
The industrial landscape around Big Pit was designated a World Heritage Site by UNESCO in 2000.

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