Broadway, the main drag in downtown Saratoga Springs, is lined with quaint mom-and-pop shops, a few chain stores, a great bookstore, a smattering of eateries, and playful life-size fiberglass horse sculptures, each painted with a different motif—remnants of the Horses Saratoga Style public art events held in 2002 and 2007. Mixed in with the horses are five-foot-tall fiberglass pointe shoe sculptures (Saratoga is, after all, home to the National Museum of Dance), each of which also bears a unique design, a favorite being “Fettushoenie Alfredo,” complete with a fork.

The best place to view it all is on the columned terrace about eight feet above street level at Maestro’s at the Van Dam. Housed in the soon-to-be-reopened Rip Van Dam Hotel, the town’s largest existing hotel from before the Civil War, this restaurant provides a bird’s-eye view of locals enjoying an evening promenade, Skidmore College students heading out for the night, and racing fans discussing a mudder’s odds in the third. It also serves up a dinner that comes in lengths ahead of the competition.

Try This: Before you’re halfway through perusing a very tempting menu, a friendly waiter will arrive at your table with a complementary white-bean salad, mixed with pine nuts, onion, pesto, fennel, and garlic, and some honey-oat bread topped with butter with Hawaiian red sea salt. Pop open a bottle of Saratoga Spring Sparkling Water and begin with agrodolce meatballs—succulent orbs of beef in a sweet and tangy sauce—served with grilled flatbread. Order the pumpkin ravioli with brown sage butter, butternut squash, toasted walnuts, chive oil, chèvre, and toasted pumpkin seeds. Finish it all off with a dense chocolate cake with chocolate buttercream, salted caramel, and ganache.