And they’re off … Cape Cod parties celebrating Kentucky Derby Day 2026 on May 2, that is.
If you have a fancy hat but don’t yet have a place to wear it, check out these local events. Most are accepting walk-ins, as space allows.
The Kentucky Derby at Bayzo’s Pub, at Brewster’s Ocean Edge Resort & Golf Club, 2907 Main St., Brewster, is from 5 to 7 p.m. on May 2. Expect signature Derby Day cocktails and snacks including fried chicken wings, bourbon-glazed ham and cheese sandwiches, cheese and raw veggie platters, finishing with a Derby Day classic: banana pudding. There will be a hat contest and a chance to cheer on your favorite horse. Cost: $40 ($61.20 with fees). Reservations: oceanedge.com or call 508-896-9000.
Cape Cod Beer in Hyannis is holding a daylong Derby party from noon to 9 p.m. May 2 in its tasting room at 1336 Phinney’s Lane, Hyannis. Sarah Swain and the Oh Boys provide live music starting at 6 p.m. Red River BBQ starts serving food at 3 p.m., including its Derby Day special Kentucky Hot Brown Sandwiches. Signature cocktails will be sold, as well as Cape Cod Beer’s 15 brews on tap.
Multiple TVs will be on for pre-race activities, with the sound added at 6 p.m. for the big event. “We’re bringing Churchill Downs to you with an afternoon full of great food, drinks, and Derby Day excitement,” according to an announcement from Cape Cod Beer.
The event, which includes prizes for best-dressed, is free, but guests are asked to register at eventbrite.com for planning purposes.
Woodford Reserve bourbon is collaborating with Wequassett Resort & Golf Club in East Harwich for a “Dapper Derby Party” at the resort. The event begins at 4:30 p.m. May 2 at 2173 Route 28. The $72 ticket ($86.40 with fees) includes a welcome cocktail and Southern-inspired light bites, a curated bourbon tasting, and live entertainment. “Dress in your finest, don a statement hat, and celebrate the Run for the Roses — complete with a best-dressed prize and seaside style,” reads the party announcement. Reserve at opentable.com.
Got a great hat? Falmouth Raw Bar is looking for you. According to its Instagram, Falmouth Raw Bar is hosting a Kentucky Derby Party starting at 5 p.m. May 2. “Watch the race, sip mint juleps, and compete in our Best Hat Contest — $100 Gift Certificate to the winner!”
At the Dunbar House Tea Room & Wine Bar in Sandwich, they had us at Peach Bourbon Scone. That’s the kickoff to a special Derby Day afternoon tea ― yes, there are hush puppies ― served 11 a.m. to 4 p.m. May 2. Make reservations through resy.com.
Shipwrecked in Falmouth Heights got an early start on its Derby Day celebration with a Facebook video showing four specialty cocktails “racing” across the screen, pulled on strips of paper. Shipwrecked’s real-time Derby Party, which involves watching the Kentucky Derby on multiple screens, kicks off at 6 p.m. May 2. (Post time is estimated at 6:55 p.m.)
Gwenn Friss is the editor of CapeWeek and covers entertainment, restaurants and the arts on Cape Cod, Martha’s Vineyard and Nantucket. Contact her at [email protected].
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