IT COMES AS NO SURPRISE that at 22, Hillary Dobbs is already breaking horse-jumping records. After all, her parents, Debi and Lou Dobbs (the former CNN anchor), live on a 300-acre horse farm in New Jersey. The Harvard grad has won 24 Grand Prix titles, is the youngest Hampton Classic Grand Prix winner and has surpassed the million-dollar mark in career winnings. What we find most impressive is her humility and the joy she finds in the little things, like ordinary horseback riding with her horse, Corlett, and spending time with friends and family.

1 | The Hampton Classic, but I’m biased. It’s such a historic horse show with a tremendous atmosphere, and my whole family usually comes. Walking out onto the grass on Grand Prix Sunday after a clear round is always a highlight. 240 Snake Hollow Road, Bridgehampton; hamptonclassic.com

2 | My favorite restaurant in the Hamptons is Trata. I go as much as possible! 1020 Montauk Hwy., Water Mill, 631-726-6200; trata.com

3 | Shopping is a guilty pleasure of mine; I could spend all day doing it! My favorite shops are Intermix and Henry Lehr. 87 Main St., East Hampton; intermixonline.com. 16 Newtown Lane, East Hampton

4 | Whether it’s looking at websites for discount designer shopping or looking on eBay, I love to shop online!

5 | After winning the $200,000 FTI Grand Prix, receiving my David Yurman watch from him and shaking his hand was very exciting! London Jewelers, 2 Main St., East Hampton, 631-329-3939; davidyurman.com

6 | Singing. I sing all the time—when I’m riding, when I’m working out, and sometimes I even get to perform The National Anthem.

7 | I have a lot of songs and artists that I love, but Stevie Nicks remains my favorite. She’s strong, unique and an individual, in addition to having a fantastic voice!

8 | It’s an honor to wear my red USA team jacket and American flag Parlanti boots, especially anytime I’m representing the country. parlanti.com

9 | I have a few favorite riders: McLain Ward, Beezie Madden, Penelope Leprevost, Marcus Ehning and Meredith Michaels-Beerbaum, just to name a few.