The 24-year-old Simmons registered his career-best score in a total of 574 for eight declared.
His marathon effort was terminated by Ryan Sidebottom’s first first-class success in six months: trapped leg before from around the wicket.
England put the quality of the surface into context by racing to 134 for two by the close.
Although Alastair Cook sliced to gully first ball, captain Andrew Strauss and Ian Bell both struck half-centuries.
Bell extended his tendency to get out when well set, however, failing to take advantage of being dropped on 49, when five overs from the close he was bowled around his legs sweeping leg-spinner Gavin Wallace.
England were given 28 overs to occupy on the second evening by a West Indies second string intent on making their opponents labour ahead of next Wednesday’s first Test.
The declaration came not with Simmons’ departure but following a quick double strike from Steve Harmison after the tea interval.
Simmons hit eight sixes and 26 fours during more than nine and a half hours at the crease, and was also given a helping hand by England midway through the afternoon session when two separate overthrows in one incident gifted him a seven.
Nibble
Simmons played spinner Graeme Swann into the off-side and ambled for a single, which turned into a three when Harmison’s wayward throw was missed by wicketkeeper Matt Prior, and gained further value when James Anderson’s powerful return from midwicket ricocheted off the stumps at the batsman’s end to the rope at third man.
That comedy of errors highlighted the lethargy which infiltrated the fielding side in testing circumstances.
Lancashire pace bowler Anderson doubled his personal wicket tally in the morning session when, after working Sewnarine Chattergoon outside off-stump, he induced a nibble through to Prior.
But the batsman-friendly conditions saw Simmons celebrate the second 200 of his career in the next over, sent down by Paul Collingwood, with a clipped single off his pads.
He resumed a second morning, starting 16 minutes early to make up for time lost to bad light last night, on 171 and in aggressive manner.
Swann was driven majestically through the covers for four and then cracked for a flat, straight six - Simmons’ sixth of the innings.
A square-driven four off left-armer Sidebottom took Simmons, dropped late yesterday evening by Prior off Anderson, to within one more boundary of his landmark.
The first hour’s run rate was slower than other passages of play, emphasised as the home team managed just 51 runs in 17 overs.
But Simmons, nephew of former West Indies all-rounder Phil Simmons, pressed the accelerator in the next hour, clearing the rope for a seventh and eighth time in one Kevin Pietersen over.
Durham paceman Harmison’s post-lunch spell then reaped a double breakthrough: extra bounce undoing Leon Johnson and a fortuitous leg before decision accounting for home captain Darren Sammy.
It was during that period that Lancashire all-rounder Andrew Flintoff appeared briefly as a substitute fielder.
Flintoff, left out of this match as a precautionary measure, tested out his side strain this morning when he warmed up alongside his fellow bowlers during pre-play practice, sending down three deliveries at a very gentle pace, and later headed to the nets for a more extensive workout.
In order to make the first Test in Jamaica on Wednesday, the 31-year-old needs to be bowling again at full tilt by the start of next week.
Harmison finished with four for 101 after accounting for Devon Thomas and Kevin McClean during a spell in which the bowlers managed to exact some reverse swing.
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