In the Maryland State Fair’s first weekend of racing this year at Timonium Race Course, the skies may finally clear for Happy Clouds and trainer Ryan Gillespie. The 5-year-old mare is uniquely prepared to snap a 10-race losing streak in the $75,000 Shine Again Stakes on Saturday. “This year, she’s gotten faster with age,” Gillespie said. “It’s crazy, but it happens, and that’s just the way it is sometimes.” Racing at Timonium may feature familiar faces from around the Mid-Atlantic region, but the track’s five-furlong configuration can lead to quirky results and sudden improvement. Happy Clouds trains at Charles Town, a six-furlong track, and Gillespie said her ample experience over a smaller oval will help the mare in what could be her first stakes victory. “I like her better going in here, and it’s almost a home-field advantage for her because she’s coming out of Charles Town,” Gillespie said. “It’s very similar.” :: Access the most trusted data and information in horse racing! DRF Past Performances and Picks are available now. Track specifications may be bending in Happy Clouds’s favor, but the track hasn’t mattered much as she has steadily improved. In the spring, the mare resumed her quest for a stakes victory in a pair of $125,000 races, the Skipat at Pimlico and the Alma North at Laurel Park. She ran respectably behind better horses in those attempts, but in the $100,000 Love Sign at Colonial Downs last month, she took advantage of a slightly softer spot to finish second by 1 3/4 lengths. The 77 Beyer Speed Figure she earned was her best since her first start for Gillespie in May 2024, which was also her last victory, an allowance score at Charles Town. Gillespie said that jockeys Arnaldo Bocachica and Jackie Davis formed a solid bond with the mare in the past, but the trainer noted that her new collaboration with Denis Araujo has been just as fruitful. He will ride her for a third straight race after working closely with her the past few months. The stars seem to be aligning for Happy Clouds in the Shine Again, and the 5-2 third choice could benefit even more if Chapa stays home. Trainer Bernie Houghton has cross-entered the 9-5 morning-line favorite in an allowance at Penn National on Friday. Before a tough trip on the turf last month, the Pennsylvania-bred finished third in the $100,000 Unique Bella in June. If the favorite doesn’t ship to Timonium, Happy Clouds’s strongest rival in the field of six will be Discreet Ops, a 4-year-old filly trained by Ben Feliciano Jr. She last ran in March, when she earned her first victory in nearly a year in an allowance race. Discreet Ops has notched all three of her career victories, as well as several strong stakes finishes, at Laurel. She is one of two runners in the field, along with 5-year-old mare Ginger Girl, who still need to prove themselves around the bullring at Timonium after disappointing finishes in the Shine Again last year. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.