The four-year-old chestnut filly won the 1 1/16-mile event by 2 ¼ lengths, in what was her first added-money triumph, defeating runner-up Roving Angel and multiple stakes winner Bear Now.
For the Josie Carroll trainee, the victory was her fourth score and first since an allowance triumph last July, a race that marked her third consecutive win.
It also ended a string of three straight runner-up finishes, including two to millionaire Bear Now: the Hill 'N' Dale on June 21 and the Ontario Matron on July 20.
Regular rider David Clark kept Serenading at the back of the five-horse field (Dance to My Tune was scratched) and watched as Star Operator and Bear Now slugged it out through opening splits of :23.72 and :47.03.
On the turn, Clark rallied Serenading along the rail and the daughter of A.P. Indy responded, easily edging away from her rivals down the lane.
Clark felt the race set up perfectly for the bay, who now has 11 top-three finishes from 12 starts.
"I thought it (pace) was pretty honest," said Clark. "My filly was very relaxed today and I had a lot of horse under me at all times. She seems to like to be in between horses and fight, so that's what we did. She's gotten better every start."
Carroll said the Kentucky-bred, who finished third to Arden Belle in last year's Belle Mahone, was full value for the win.
"We're delighted," said Carroll, of Serenading, owned by John and Glen Sikura. "This filly is so deserving. She lays it on the line every time."
Serenading returned $6.70, $3.50 and $2.10, combining with Roving Angel ($4.30, $2.40) for a $28.60 exactor. Bear Now paid $2.10. Triactor wagering was not available.