The 144th-annual Kentucky Derby takes place on May 5, which also happens to be Cinco de Mayo, so it's gonna be a big day for parties. Dubbed the "most exciting two minutes in sports," the race features about 20 horses competing for a $2 million purse. It's also the first in the Triple Crown series of races — which includes Preakness Stakes on May 19 and Belmont Stakes on June 9. The derby's post time is 6:34 p.m. but plenty of Cincy bars and restaurants are starting the party earlier in the day with drink specials on traditional mint juleps, best dressed competitions and more.
Covington Trifecta Derby Party —The most exciting two minutes in sports are (arguably) best spent sunburnt and muddy in the infield of Churchill Downs, but Braxton Brewing is throwing an alternative party in honor of the 144th Kentucky Derby. Tipping their floppy hats to the Run for the Roses, the Covington brewery will have Kentucky Home mint-julep style beer — an ale aged in bourbon barrels with mint — on tap along with heated competitions for Best Dressed, Best Hat and Best Couple. Braxton neighbors Hotel Covington and The Hannaford are also in on the fun: visit all three locations and you’re in on a raffle for a slew of prizes, including a cocktail class at the Hannaford. Noon-8 p.m. Free. Braxton Brewing Company, 27 W. Seventh St., Covington, braxtonbrewing.com.
Urban Derby in OTR — If you’d rather not cross the bridge to bask in the bluegrass on Derby Day, consider heading over to Union Hall for an “urban derby” experience, featuring student Hip Hop performances, a live painting session by mural artist Xylene and a silent auction. Hosted by Elementz Hip Hop Youth Art Center, the event raises funds for the community space that “fosters and channels the creative self-expression of Cincinnati’s inner-city youth through music, dance, poetry and art.” The $100 entry fee covers eats and sweets along with an open bar stocked with Derby-themed drinks from Revel OTR, Listermann Brewing Company and Rhinegeist. The unique party promises excitement, but start prepping now for the “flyest kicks” and “freshest hat” contests. 4-7 p.m. $100. Union Hall, 1311 Vine St., Over-the-Rhine, elementz.org.
College Hill Derby Day Party — This Derby Day party, held at historic Laurel court and hosted by the College Hill Community Urban Redevelopment Corporation, will benefit the organization’s efforts to revitalize the Hamilton Avenue business district and strengthen the surrounding neighborhood. Attendees will enjoy a free mint julep, Derby-themed catering, a silent auction and a lineup of fun and games. 5-10 p.m. Saturday. $75-$85. Laurel Court, 5870 Belmont Ave., College Hill, chcurc.com.
Derby Day Party at Hotel Covington — Hotel Covington celebrates Derby day with a menu of Kentucky classics at Coppin’s, including hot browns, bourbon-smoked chicken wings, hush puppies and cocktails. For drinks, there will be a special Frozen Lily — a take on the Derby’s other famous drink, with vodka, lemon juice, cranberry and orange — plus classics, like a mint julep. Check out the pop-up tie bar before the Best Dressed competition, and interact with a real horse, who will be on site. 10 a.m.-7 p.m. Free admission. Hotel Covington, 638 Madison Ave., Covington, hotelcovington.com.
Derby De Mayo Charity Crawl — It's a crossover bar crawl for charity: 100 percent of the entry fee goes to Planned Parenthood Southwest Ohio's Access, Care & Treatment fund. Start the crawl by registering at the Treehouse Patio Bar and then make your way to Wiseguys, Below Zero Lounge, Sundry and Vice and The Pony OTR. 2-9 p.m. $27.03. Treehouse Patio Bar, 1133 Sycamore St., Over-the-Rhine. Event info here.
Derby de Mayo Presidential Style — The Presidents Room is hosting a mash-up party featuring tequila juleps, bourbon margaritas and more cocktails, plus chips and dip with guacamole and pimento cheese. Wear festive Derby-style hats for a chance to win a tasting menu dinner for two. 5-10 p.m. Free admission. The Presidents Room, 812 Race St., Downtown, facebook.com/presidentsroom.
Oakley Wines Kentucky Derby Party — Celebrate at Oakley Wines with mint juleps, bourbon slushes and a Derby Day food. TVs will screen pre-race activities and the official Derby at 6:34 p.m. Ladies, wear your best hat. Gents, wear your most dapper bow tie. 3-10 p.m. Free admission. Oakley Wines, 4011 Allston St., Oakley, facebook.com/freedrinkinglessons.
Queen City Derby Party — Get a lil' fancy at this fundraiser for the DGL Foundation. The party features live music, a Derby viewing (with betting), food, cocktails — including complimentary mint juleps and Oaks lilies — and a focus on fashion. Women and men are encouraged to dress their best. 3:30-9:30 p.m. $80. Anderson Pavilion, 8 E. Mehring Way, Downtown. Tickets and info here.