When two day-drinking holidays collide, particularly on a weekend, one has to jockey for first place on the event schedule. Ironically,the Derby seems to be losing that race, with the quantity of Cinco de Mayo parties in Baltimore pulling far ahead on May 5. That said, whether you plan to sport a sombrero or a fascinator, there are still some quality events at which to quaff while taking in the races.

 

This year’s annual Howard County Cup Races coincides with the Kentucky Derby, and there’s hardly a better way to celebrate both traditions than at this outdoor party at Pleasant Prospect Farm in Brookeville. Watch the local races in person followed by a Derby viewing, all with the backdrop of the yearly Tailgate Contest. Gates open at 12:30 PM for tailgate setup with festivities and judging beginning at 2 PM. (4389 Jennings Chapel Road)

 

Laurel Park
Kick off the Triple Crown at Laurel’s Kentucky Derby Day party with live racing and a Derby simulcast. Gates open at 10 AM with three Derby buffets, Triple Crown drinks in souvenir glasses, and three different Derby buffets as well as reserved seating in the the Silks Room. (198 Laurel Race Track Road; 301-725-0400)

 

This Federal Hill bar is aptly acknowledging the coinciding drinking holidays on May 5 with their Cinco de Derby party. Start off the day with bottomless brunch ($15 crushes, sangria, Bloody Marys, and mimosas) between 10 AM and 3 PM, then stick around for Derby Day drinks and the races, including options for reserved tables with drink packages. Email events@thecharlesbaltimore.com for reserved tables. (1110 South Charles Street; 410)-727-2333)

 

This Canton bar will be celebrating both the Derby and Cinco de Mayo with its 5th Annual Kentucky Derby Block Party, the proceeds of which will benefit the St. Francis Neighborhood Center. Watch the races on the outside TV wall to the backdrop of live entertainment from DJ AYYYE ONE, Ricky Wise & The Dirty Unit, AstroSquid and Victims of Experience. Food stands include tacos, burgers, BBQ, oysters, macarons from Balti’Marons, and ice cream sandwiches from Cream Cruiser. A full bar will be inside, but beer trucks will be pouring UNION and RAR brews, tents will be up for Waverly Brewing Company, Key Brewing Co., Monument City Brewing Company and Jack's Hard Cider, and beer tubs will be on hand with Natty Boh and Tecate 16 oz tall boys. Liquor lovers can stop by either the Three Olives Vodka Bomb Bar or the Maker's Mark Mint Julep Bar. $10 cover. (3328 Foster Ave; 410-327-6984)