Eat and Drink

Roundup: Where to Celebrate Cinco de Mayo/Kentucky Derby

On Saturday, May 5th, Cinco de Mayo and the 144th Kentucky Derby will be happening simultaneously. It probably goes without saying, but #Southie will be HOPPING. Check out all the many ways you can celebrate Cinco de Derby (Kentucky Mayo? I’ll keep working on it) in the neighborhood. Note: many of these are 21 and over, so check beforehand if you’re bringing kiddos.

Amhreins: They’re doing a Derby de Mayo event on Saturday—put on your poncho and derby hat! There’ll be prizes for outfits and specialty drinks like margaritas and mint juleps.

Barlow’s: Barlow’s will celebrate both events. Their Derby ticketed event, 4-7 pm, has a $20 cover for a complimentary buffet and drink specials like the mint julep, Kentucky mule with ginger beer, and even Kentucky Bourbon Barrel Ale on tap. There’ll be a best-dressed contest, and the whole thing’s a fundraiser for Joseph “Dodo” Nee South Boston Collaborative Center. Stick around afterwards for their Cinco party.

Boston Taco Fest: (family friendly) Boston’s first taco festival will be at City Hall from 10 to 10 Saturday and Sunday. There’s so much going on, including Mexican cuisine, live music, pro wrestling super shows, taco eating contest, best taco competition, and free lemonade from Hubert’s.

The Broadway: Broadway’s throwing a Kentucky Derby party with swag, mint juleps in silver plated cups, and a best hat competition for a $250 gift card.

by CHLOE: For a vegan take on Cinco de Mayo, by CHLOE. is offering their favorite Quinoa Taco Salad with a special edition Quinoa Horchata with Rice Krispie Treats Chill by CHLOE. push pop, available for $13.95 at their Seaport and Fenway locations. This special will take place Friday, May 4th – Sunday, May 6th!

Capo: Capo will be hosting a Kentucky Derby Day Party in the Supper Club. There’s no cover charge, and it’s first come first serve with doors opening at 3:30. Steve Memmolo and the Classic Yellow Band will be playing starting at 4:15 until the race, which will be broadcast. Their Derby cocktails are Mint Julep, Pimm’s Cup, and Whiskey Smash. Best-dressed male and female get a prize!

Coppersmith: They’re hosting a Southie Derby Party all day long on Saturday. If the weather’s nice, they’ll break out their Airdeck flat-screens; otherwise, they’ll have their projection screens showing the race. Mint juleps will be flowing, and the best hat wins $100 in prizes.

Drink: Drink’s ninth annual Derby Party has lots going on: a $75 ticket will get you three cocktails, a Derby-themed menu, fun and games, and a commemorative julep cup.

Gather: Enjoy the “most exciting two minutes in sports” with big hats, beers & bourbon! Gather will be offering Derby Day themed food, drinks (Mint Juleps!), games & prizes – plus our Triple Crown winning craft beer list.  Bulleit Bourbon, Angry Orchard Rosé and Mr. Sid will joining in the festivities! Be sure you dress to impress, they’ll have prizes for the best dressed man and woman. Reserve your spot here! 

The InterContinental Boston: The InterContinental Boston and special guest Jonathan Soroff, Feature Writer and Social Columnist of The Improper Bostonian, invite guests to partake in a fun-filled evening on Saturday, May 5th where fashion and sport meet in celebration of “Talk Derby To Me” on the Promenade at The InterContinental Boston.  The complimentary outdoor event is open to the community at large and will include:passed light bite Southern Fare crafted by the hotel’s Executive Chef Didier Montarou, Lawn games including Cornhole, life-size Connect Four and Jenga, “The Most Exciting Two Minutes in Sports” being televised outdoors on the Promenade. Gentlemen are encouraged to wear bow ties and ladies to don their favorite big hat, as prizes will be awarded by guest judge Jonathan Soroff, Feature Writer and Social Columnist of The Improper Bostonian, for ‘Best Bow Tie’, ‘Best Hat’ and ‘Most Derbyish Couple’ for a chance to win a gift certificate to Miel Brasserie Provençale at The InterContinental Boston!

The Junction: There’ll be margarita specials, $5 tacos, $50 gift card for best dressed, and mint juleps. The race will be broadcast, with TVs in every direction per usual.

Kings: Their Cinco de Derby event celebrates both occasions at all their locations, including Seaport and Back Bay. They have mint julep margarita specials, race contests that let you pick which horse you think will win, DJ, dancing, and giveaways. Wear your hat!

The Lawn on D: (family friendly) The fifth annual season kicks off with a Cinco de Mayo celebration on Friday and Saturday with Latin and mariachi bands and fun family activities like face painting.

Lincoln: Their rotating Brunch Test Kitchen menu will be Cinco themed, and see if you can spot a few Star Wars references (May the 4th be with you!). They’re also promising six drink specials. For Cinco, their specials are inspired by the nearby Loco: the El Jefe Margarita, the Coco Margarita, and their own specialty cocktail the Dracarys. For the Kentucky Derby, they have Sam Adam’s Rose Cider, the Talk Derby to Me, and the classic mint julep.

Loco: Oh my god, so many things. They’re doing 5 Days of Cinco, with a different event every night. On Monday they’re doing Loco for the Coco, with frozen coconut margaritas in a pineapple. If you tag your marg picture with #locoforthecoco, you’ll be entered to win a custom skateboard from Pacifico. On Taco Tuesday, they’ll have taco trays and Cinco margarita pitchers. One tray will have a golden ticket worth $150 for a free taco box for 10 people and authentic Mexican glassware. On Wednesday, they’re partnering with Cisco Brewery for Cisco de Mayo, which includes a taco-eating contest. Eight teams of four compete, and winners get a free trip to Cisco brewery, swag, beer, and the bill covered for all the tacos they ate. Thursday has live music 8-11 pm and the return of the Poptail (a.k.a Boozy Popsicles). If you submit your own Poptail recipe, you’ll be entered to win a custom snowboard. On Friday, they’re open early at 11:30 for their Rum Punch Lunch. They’ve got their signature rum punch in a watermelon and live music in the evening. If you guess how many watermelons they sold last season, you’ll win a Modelo bag toss game. On the big day: doors open at 10 am, and there’s door prizes, contests, and giveaways including 28 piñatas that each have goodies like Red Sox tickets, candy, and swag. They’ll have a golden margarita (Espolon Anejo X with a Grand Marnier float) and a mariachi band that’ll play every time someone orders one. And finally, on Sunday, there’s a hangover brunch called Rosé and Shine with enormous bottles of rosé, an Instagram photo contest with a hangover care package going to the winner, and live music from DJ Lazee Boy.

Publico: Their Roses & Ritas Cinco de Mayo and Kentucky Derby party will feature juleps, tequila cocktails, carnitas, and mahi mahi tacos.

Punk and Poet: Go for a more casual ambiance, with some decorating, buckets of Corona, the race on TV, piñatas and giveaways, and their regular brunch until 3 pm.

Roza Lyons: Similarly, it’ll be a casual affair: some mint juleps and Coronas, with the race on TV.

Social Register:  Get your big hats and seersucker suits ready! Join Boston Good Sports Boston Young Professionals Board at The Social Register on Saturday May 5th for the 7th Annual Good Sports Boston Young Professionals Board Kentucky Derby Party. Decked out in your Derby best, guests will enjoy light hors d’oeuvres and your first two drinks on Good Sports! There will also be an exciting raffle and a best dressed contest with some prizes you won’t want to miss out on. This event sells out fast so make sure you buy your tickets early! You can purchase your tickets here! 

The Seapoint: The Seapoint’s Comedy Night returns with a special Cinco de Mayo themed event, hosted by Boston comic Kyle McNally starting at 8 pm.

Worden Hall: Their Kentucky Derby Party will run from 3 to 7 pm. There’ll be mint juleps with Four Roses Bourbon, and guests are encouraged to dress up in their best Kentucky Derby getup.

And these are just places nearby. If you’re looking to venture out of Southie, there’s plenty to do. If your favorite spot isn’t listed here, keep checking their social media—some restaurants and bars haven’t finalized their plans yet.

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About the Author

Katherine J. Igoe

Katherine J. Igoe is a freelance writer and editor who freely admits she just moved to Southie with her husband in 2017. Loves writing about local food, culture, and space savers, as well as more serious things like mental health. Follow her/send her ideas on Twitter @kjigoe.