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Boston’s Best Spots To Watch The 2024 Kentucky Derby

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Boater or fascinator? A hat is said to bring good luck for those who are celebrating the 150th run of the Kentucky Derby, (rather than Star Wars Day) on May 4. Derby style advises that the topper dictates the rest of your wardrobe. A flamboyant hat may call for a more streamlined outfit, where a simple chapeau invites a flashy ensemble. Whatever you choose, there’s a spot in Boston to show it off. The festivities this year range from drop-in drinks to elegant soirees. Here’s a round up of top spots for watching the most exciting two minutes in sports.

Dress to Impress at The Newbury Boston: The see-and-be-seen crowd will be flocking to this hotel, which opened nearly 100 years ago as one of the first Ritz Carlton hotels in the United States for live music, Derby-inspired hors d'oeuvres, expertly crafted cocktails, Whispering Angel Rose and an exquisite Bourbon Tasting featuring Woodford Reserve— the official sponsor of the run for the roses. Naturally, The Newbury will be serving its own delicious riff on a Mint Julep, and Boston man-about-town Jonathan Soroff and self-proclaimed “one-man Mardi Gras” will serve as emcee.

Tickets are $95, plus tax and gratuity, per person, or pay $170 per person and receive a limited edition 150th Anniversary Kentucky Derby Woodford Reserve Bourbon Bottle. Highgate Charitable Foundation, which benefits children’s health and welfare, will get $5 from every ticket. Saturday May 4, 2024 from 4 p.m. - 7 p.m. Tickets available via Explore Tock here. 1 Newbury St., Boston

Party Down at High Street Place: Have your own paparazzi moment as you walk the custom green carpet and Rhode Island based comedian Brian Vincent asks you about your Derby look and winning pick. You can bet that Miss Massachusetts 2024 Melissa Sapini, and Miss Maine 2024 Summer Baldridge, who will each be in attendance, will be sporting some show-stopping attire. You can’t miss High Street Place's massive LED video entertainment wall, the largest in the city, where they will broadcast the game, but in case you’re distracted by a game of Cornhole, Jumbo Jenga, Jumbo Connect Four, and High Street Place’s custom Pop-A-Shot, set up all around the food hall, Derby trumpeter, Sara Manning of the Harvard University Band will perform “Call to Post” just before the race begins.

The event, in partnership with Down & Derby, will benefit Love Life Now Foundation (LLN), a New England based organization dedicated to promoting awareness and prevention around domestic violence, through their initiatives. Party goers can purchase 50/50 raffle tickets and place them in the mason jar representing the horse they think will win. The winner will be drawn from the jar representing the triumphant Kentucky Derby horse and Love Life Now Foundation will receive the other half of the total bets.

Tickets are $65, and include admission, door prize chance, complimentary hors d’oeuvres, an Aperol Spritz tasting, and dessert. Elite tickets ($80) include all of the above plus a complimentary cocktail from the event’s menu. All attendees must be 21+ and have a valid ID. Saturday May 4, 2024 from 4 p.m. - 8 p.m. Tickets available here. 100 High Street, Boston

Stop and smell the roses at Nautilus Pier 4: No tickets are required to enjoy lush greenery and florals by the celebrated local designers at Winston Flowers in the Nauti Garden, which overlooks Boston Harbor. But reservations are highly recommended if you want to enjoy a meal in the main dining room or patio. The bar is first come, first served and walk-ins are welcome. Saturday, May 4, 2024, 12 p.m. to close, Pier 4 | Boston Seaport, 300 Pier 4 Blvd., Boston

Try your luck at Encore Boston Harbor: While you can’t bet on the horses, you can play casino games over 210,000 square feet of gaming space, then check ouot the race on their 10-foot-high, 123-foot-long video wall, while enjoying specialty cocktails featuring Woodford Reserve, prize giveaways, and a “Best Dressed” competition. No reservation or ticket needed. Saturday, May 4th, at 4:00pm, WynnBET Sportsbook, Encore Boston Harbor, 1 Broadway, Everett

Watch from the drunk tank at Alibi: Set in the old “drunk tank” of what was the Charles Street Jail— now the luxe Liberty Hotel—Alibi Bar & Lounge promises to be packed with Southern charm and thrilling horse racing action— especially on their private patio. There will be a best-dressed prize and a giant projector to show the race, alongside signature flavors of the South with specialty cocktails, including the iconic Mint Julep. Free for all who RSVP. For more information, click HERE or call (857) 241-1144. 215 Charles Street, Boston

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