After a dreamy afternoon at Willow Creek Winery, where rosé flights and vintage Gucci reigned supreme, my husband, our best friends, and I weren’t ready to call it a day. It was still Derby Day, after all—and in Cape May, that’s basically a high-fashion holiday with a side of bourbon.
Our next stop? Elaine’s—a vibrant, historic Cape May spot that decided to go all in on Derby Day festivities. And when I say all in, I mean wall-to-wall horse décor, full themed cocktails (see: the Maple Old Fashion and Run for the Rosé), and a sea of women in hats that could have their own Instagram handles.
Vibes: Immaculate. Staff: Overwhelmed. Me: Thriving Anyway.
Let me set the scene: the place was absolutely buzzing. Hats brushing shoulders. Men in suspenders pretending they know horse stats. Champagne flutes (okay, maybe not flutes, more on that in a second) clinking between cheers. It was the kind of energy that feels like the Kentucky Derby collided with a bachelorette party in the best possible way.
That said, the bar was not prepared for this level of enthusiasm. The drink line moved about as fast as a horse on its third mint julep. So, instead of testing the bartender’s ability to craft a Vodka Spire under pressure, I went with a mimosa in a wine glass. Classic. Reliable. Effervescent. Like me at 8 PM in sneakers instead of heels.
Speaking of which—I had officially retired my NYFW-adjacent Derby outfit post-Willow Creek. Gone was the glam. In its place? Comfy clothes and a carefree attitude (see photo above for a visual of “Chic But Practical Taylor”). And let me tell you, I didn’t miss the outfit—or the pinching shoes—for a second.
Balloon Animal of the Night
Elaine’s didn’t skimp on the decor. I’m talking horse balloons around every corner—each one more tempting than the last. Naturally, I claimed one as my own and proudly paraded it through town like a trophy. It brought joy, attention, and more than one “Where’d you get that?!” from strangers. Tragically, the wind had its own plans, and my majestic steed floated away into the Cape May night sky. RIP.
Final Thoughts from a Derby Day Convert
Was the drink wait long? Sure. Was my mimosa in a proper flute? Nope. But you know what? The energy, the music, the hats, and the pure fun of being surrounded by friends made every second worth it.
It wasn’t about what was in my glass—it was about who I was clinking glasses with. And that, my friends, is the real winner’s circle.
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