You do not need to be at Churchill Downs to celebrate the “The Fastest Two Minutes in Sports” on May 2nd. Experience this year’s Kentucky Derby in style at these events:
Kentucky Derby Pup Races, Park-9 Dog Bar, Everett | 3:30-7:30 p.m.
Why should horses get to have all the fun? Sign your beloved Corgi or Dachshund pup up for a chance at glory at the Park-9 Dog Bar’s very own derby. New this year there will be open heats for mixed small dogs. Derby attire encouraged for dogs and humans alike. Prizes will be awarded to the dogs sporting the best derby outfits. Winners will receive prizes from Park-9 and Tandem Vet. All dogs and humans are invited to sip on a mint julep and cheer on the racers! Register your racer at park9dogbar.com.
Kentucky Derby By the Sea, Emerson Inn, Rockport | 4:30-9 p.m.
Make sure your hat is tops because this event will offer a “Best Hat” competition along with live music. Tickets include a special sparkling welcome drink, hors d’oeuvres, and event access. Make it a night by adding on a dinner reservation and enjoy options like bourbon-glazed salmon with maple and pecans, Hot Brown Kentucky Dinner, and peach cobbler with maple and bourbon.
Ironstone Derby, Ironstone Farm, Andover | 3-7:30 p.m.
Bring out your inner jockey with a stick horse race and get up close with Ironstone’s herd of 22 horses. This family-friendly event includes food from Ben & Jerry’s, Crack’d Kitchen, and Lucy’s Libations – with a special vendor from Mixed Metals! Pony rides, face painting, and more culminating with a big-screen viewing of the race. More information and tickets available at ironstonefarm.org.
Kentucky Derby at Banner’s Kitchen & Tap, Boston | 5 p.m.
The action-packed evening will start with complimentary drink tickets and live music to get the party started. An à la carte menu will be offered, along with a sampling of Banner’s handcrafted beverages. Come wearing your best outfit and biggest hat for the chance to win prizes for best dressed. To elevate the evening, Banner’s is offering additional add-ons to enhance any guest experience, including, The FEAST!, Booth & Bubbles, and the Sushi Boat. A night filled with high energy, great food, prizes, and more. This is a 21+ only event, and seating is limited; early reservations are encouraged. To make a reservation visit OpenTable.
Kentucky Derby Party, Nicholson Hall, Newburyport | 5-9 p.m.
The Firehouse Center for the Arts is holding a Kentucky Derby Party to raise funds to support the local arts. Wear your best Derby attire and join them for an evening of thoroughbred racing, music, food, friends as well as a live auction! you can even bid on securing the Firehouse balcony for each evening of the 2026 Yankee Homecoming Concert Series.
The Kentucky Derby “Darty” at The Newbury Boston | 4-7 p.m.
Take a drive to Boston to enjoy live music, a selection of Kentucky Derby-inspired hors d’oeuvres, and crafted cocktails. A portion from every ticket will be donated to BINA Farm Center, which brings people of all ages and abilities together through inclusive therapeutic and equine-assisted programs.. Learn more here.
The Kentucky Derby Party at Post 1917
Celebrate the Run for the Roses in style at Post 1917’s Annual Derby Watch Party in Reading. Hosted in the restaurant’s brand-new private room, the ticketed event includes passed appetizers, a handcrafted Mint Julep, and entry into a festive evening of Derby Day excitement. Guests are encouraged to dress to impress for the Best Dressed Hat Competition, with winners taking home a Post 1917 gift bag and a $250 dining gift card valid at both locations. The celebration takes place Saturday, May 2 from 5–8PM, with limited tickets available. Tickets are available for $50 (excluding taxes and fees) through Resy.