The Willard Hotel’s annual gathering is the District’s longest-running Kentucky Derby party. It’s only fitting, since the Willard is where Henry Clay introduced the mint julep to Washington. The crowd is older than some other D.C. gatherings, but no less jocular. The $75 ticket includes two juleps, a buffet with sandwiches, sides and Derby pie, raffle entries and gifts. Pick your outfit carefully: Prizes will be awarded for the best bonnet and the most bodacious bow-tie.
Saturday from 4 to 8 p.m. The Round Robin Bar, 1401 Pennsylvania Ave. NW. 202-637-7350.www.washington.intercontinental.com. $75.
Kentucky Derby on a rooftop
If the sun is shining, there’s no better place to watch the Derby than Jack Rose’s rooftop deck. At this annual party, bartenders whip up traditional mint juleps ($9) and bourbon sweet tea ($7), and from 4 to 6 p.m., the staff passes out free Kentucky-inspired snacks. (Previous years have included personal-size derby pies and mini Kentucky hot browns.) The race plays on TVs on both floors, and admission is free, with no reservations required.
Saturday from 4 to 7 p.m. Jack Rose Dining Saloon, 2007 18th St. NW. 202-588-7388. www.jackrosediningsaloon.com. Free.
Perry Center party
The Perry Center’s fifth annual soiree is moving from the Iron Horse Tap Room to Penn Social this year, which means better views of the race, including on a 22-foot high-definition projection screen, more (free) games and plenty of room to spread out. The best-dressed competition is serious business, so look sharp. A $25 ticket includes discounted drinks, including $5 mint juleps, free appetizers, free shuffleboard and a pre-race party with DJs.
Saturday from 4 to 7 p.m. Penn Social, 801 E St. NW.www.kdp5.splashthat.com. 202-312-7140. $25 in advance, $30 at the door.
Prancin’ with real horses
A new entry into this year’s Kentucky Derby party stakes, Prancin’ is the only Kentucky Derby party in the District that will have real horses for adults to ride. Seriously: pony rides for grown-ups at the Hill Center. The Brightest Young Things party is an open-bar affair with six bartenders whipping up their own takes on the mint julep, including Alexandra Bookless of the Passenger and Rachel Sergi of Buffalo and Bergen. If you can tear yourself away from the horses, entertainment options include barbershop quartets, bluegrass and heavy metal bands, dancing to country music spun by the Outlaws DJs, whiskey tastings, and barbecue, oysters and other snacks.
Saturday from 3 to 8 p.m. Hill Center, 921 Pennsylvania Ave. SE.www.prancin.eventbrite.com. $60 in advance, $70 at the door.