15th Annual Montauk Music Festival | May 14-17, 2026

There is a specific weekend every May when Montauk stops being a place you're anticipating and starts being a place you're actually living in. For me, that weekend is the Montauk Music Festival -- and this year marks the 15th annual, presented by the Montauk Sun.

Over 400 performances. 100 acts. 40 satellite venues spread across town. Music spilling out of every bar, every patio, every corner you turn. It's the weekend the whole town feels alive in a way that's different from the height of summer -- looser, warmer, more communal. Everyone is genuinely happy to be there.

There's something happening on Park Place this week, and I think you're going to love it.

On Thursday, May 14, Walter Hagen is opening a pop-up shop right in the heart of East Hampton Village at 34 Park Place — and the timing couldn't feel more fitting. With the 126th U.S. Open Championship returning to Shinnecock Hills this summer, golf is having a real moment out here, and this store is leaning into it beautifully.

My friend has been saying it for years: Hampton Bays has a different vibe. Less scene, more vacation. Less about being seen, more about actually relaxing. And she's completely right.

If the Hamptons ever starts to feel like a performance, Hampton Bays is the antidote. And Rumba is exactly where you go to feel that shift.

There's a new shop in Amagansett that I think is going to become a staple out here, and I mean that in the truest sense of the word.

Jamagansett is a jam and bake shop born right here on the East End, built around local farmers and the flavors they grow. It's small, it's specific, and it's exactly the kind of place that reminds you why shopping local out here feels different than anywhere else.