<?php
$str = 'Saturday, August 03, 2013
DUMP Pickup: LITTLE ROCK, AR
Dest: CALDWELL, TX
HOPPER Pickup: BEECH GROVE, IN
Dest: TERRE HAUTE, IN
Sunday, August 04, 2013
HOPPER Pickup: JONESBORO, AR
Dest: BATTLE CREEK, MI
LIVE BOTTOM Pickup: JONESBORO, AR
Dest: TAYLOR, MO';
 
 
function parse_( $str ) {
    $data = array();
    foreach( explode( "\n", $str ) as $line ) {
        if ( strpos( $line, ':' ) === false ) {
            $date = $line;
        }
        elseif( stripos( $line, 'pickup:' ) ) {
            $string = $line;
        }
        else {
            $data[$date][] = $string . ' -> ' . explode( ': ', $line )[1];
        }
    }
    return $data;
}
 
print_r( parse_( $str ) );
 
 

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