Women in Love is the classic one for this, although I don't know if this meets the appropriate criteria.
Following up the Georgette Heyer reference above, The Talisman Ring deconstructs this trope. However, I think Georgette Heyer has more first encounters between hero and heroine with the hero driving rather than riding, although there is often a riding scene later on.
In Eight Cousins by Louisa Alcott, Rose first encounters her cousins mounted on ponies, and drawing a cart, which she initially mistakes for a circus procession. In the sequel, Rose in Bloom, the loss of the heroine's first love interest is occasioned by his drunkenness leading him to be incapable of managing his horse. Laurie in Little Women is supposed to be a good rider, and Amy fakes riding by putting a saddle on an old tree.
no subject
Following up the Georgette Heyer reference above, The Talisman Ring deconstructs this trope. However, I think Georgette Heyer has more first encounters between hero and heroine with the hero driving rather than riding, although there is often a riding scene later on.
In Eight Cousins by Louisa Alcott, Rose first encounters her cousins mounted on ponies, and drawing a cart, which she initially mistakes for a circus procession. In the sequel, Rose in Bloom, the loss of the heroine's first love interest is occasioned by his drunkenness leading him to be incapable of managing his horse. Laurie in Little Women is supposed to be a good rider, and Amy fakes riding by putting a saddle on an old tree.