Thoroughbreds closely associated to the Old Dominion State take center stage Saturday at Colonial Downs in New Kent, which offers a Virginia Champions Day card highlighted by five turf stakes.

The Jamestown Stakes, restricted to 2-year-olds either bred in Virginia or sired by a stallion standing in Virginia, is scheduled as Race 5 with a post time of 3:30 p.m. ET. It’s a 5 ½-furlong turf sprint and features a field of seven juveniles just starting their racing careers.

Six of the seven entrants are males, yet the one filly in the Jamestown stands out as the most likely winner. Sail Theseven Seas (#2, 6-5 morning-line odds), a daughter of Kentucky Derby winner Street Sense, enters Saturday’s race having finished second in both of her starts, which came on dirt at Laurel Park and then on dirt again at Colonial in the 5 ½-furlong Keswick Stakes on Aug. 3, also restricted to Virginia-bred or -sired horses.

Sail Theseven Seas had a rough trip in the Keswick, veering out at the break and encountering traffic on the turn and also in early stretch. The filly took a short lead late but could not last as a longshot rival rallied to win, but she did hold second.

Sail Theseven Seas’ Equibase Speed Figures are superior to every other 2-year-old in the Jamestown, and while it is certainly true that any one of these runners can make significant improvement from start to start at such a young age, this may be a not-uncommon case of a female maturing earlier than her male counterparts.

Horacio Karamanos, one of Colonial’s leading jockeys, keeps the mount after riding this filly in both of her starts for trainer Mike Trombetta, who’s having a typically strong meet at the Virginia track. I’m expecting a smoother trip for this filly and for her to handle a switch to turf with ease, and therefore I’m keying her on top of both exacta and trifecta tickets.

I’ll use three horses underneath Sail Theseven Seas in a $4 exacta (totaling $12) and a $1 trifecta (totaling $6) for a total spend of $18 on the Jamestown. They are War Humor (#3, 6-1), Dedicated Hero (#5, 30-1), and Wheneveruremember (#6, 8-1). War Humor has some decent turf bloodlines and improved in his second career start to finish third in a nine-horse field going 5 ½ furlongs on turf at Colonial Aug. 13. Longshot Dedicated Hero improved even more from his first to second start – from eighth to first – as he won a five-furlong dirt sprint at Penn National on Aug. 15 after setting a pressured pace. He should help to ensure a good early clip in the Jamestown along with Virginia Fitz (#7, 3-2), who won a turf sprint first out July 25 at Colonial.

Wheneveruremember is stablemate to Sail Theseven Seas and probably has the second-best chance at winning the Jamestown, as the Virginia-bred colt is by top-level nationwide sire Gun Runner and out of a mare that won The Very One Stakes on turf at Pimlico. He moved from dirt to turf for his second start and finished an even fifth of nine after lacking room to rally in the stretch in the Aug. 13 race in which War Humor finished third.

Virginia Fitz is the second favorite on the Jamestown morning line, but his win at 5 ½ furlongs came at the maiden claiming level and came on a yielding turf course. I’ll leave him off of my tickets and hopefully boost the payoffs.

My betting strategy for the Jamestown is as follows:

$4 exacta, Sail Theseven Seas over War Humor, Dedicated Hero, and Wheneveruremember ($12)

What to say at the betting windows or keystroke into the ADW field: Colonial Downs, Race 5, $4 exacta, 2 with 3, 5, and 6

$1 trifecta, Sail Theseven Seas over War Humor, Dedicated Hero, and Wheneveruremember ($6)

What to say at the betting windows or keystroke into the ADW field: Colonial Downs, Race 5, $1 trifecta, 2 with 3, 5, 6 with 3, 5, 6