Published by The League
The League launched its 2026 Hamptons summer programming with a curated weekend in Montauk, bringing together invited members and creators for VIP experiences at Surf Lodge and Montauk Yacht Club—including a HIIT Pilates class with Madison Appel and Lululemon, a “Singles for Doubles” tennis clinic, and a Wimbledon Finals watch party. It’s the first of three Hamptons weekends this summer, with more to come in the following weeks and again at the end of August.
What Happened This Weekend
The League kicked off its Hamptons summer programming with an intimate, curated escape to Montauk designed to bring ambitious singles together beyond the app. Ten members and creators joined for a weekend built around premium hospitality, wellness, and real-world connection: VIP tables and dinners at Surf Lodge, and activity-driven programming at Montauk Yacht Club.
The weekend blended high-energy social moments with intentional opportunities to connect. Friday and Saturday nights, the group came together at Surf Lodge, with Brunello performing Friday and Lil Yachty and DJ Cassian taking over Saturday. Mornings shifted the pace toward wellness and community.
The Weekend, Day by Day
Friday set the tone with a night at Surf Lodge, live music from Brunello, and the first round of introductions among the group.
Saturday opened with a HIIT Pilates class overlooking the water, led by Madison Appel in partnership with lululemon, followed by breakfast. That evening, the energy shifted back to Surf Lodge for a set from Lil Yachty and DJ Cassian.
Sunday brought the group to Montauk Yacht Club for “Doubles for Singles,” a tennis clinic with Madison Appel, followed by lunch and a Wimbledon Finals watch party. Another 30 singles turned out for the day’s programming.
Why The League Hosts Events Like This
The League’s approach to modern dating has always centered on intentionality over volume—fewer, better introductions instead of endless swiping. IRL events extend that same philosophy off the app. Shared movement, shared meals, and shared moments create a lower-pressure way for singles to meet, one where chemistry has room to show up naturally instead of being manufactured over a screen.
By creating shared experiences rooted in movement, conversation, and fun, the weekend fostered meaningful connections not only among invited members but across a broader community of singles throughout the weekend.
What’s Next
This was the first of three Hamptons weekends The League is hosting this summer. The community will reconvene in Montauk again in a few weeks, with a final weekend planned for the end of August.
FAQ
What is The League’s Hamptons programming? It’s a series of three curated summer weekends in the Hamptons, hosted by The League, combining premium social events (like nights at Surf Lodge) with wellness and activity-based programming (like Pilates and tennis clinics) designed to help ambitious singles meet in real life.
Where did the first Hamptons weekend take place? In Montauk, with events at Surf Lodge and Montauk Yacht Club.
Who performed at the Montauk weekend? Brunello performed Friday night, and Lil Yachty and DJ Cassian performed Saturday night, both at Surf Lodge.
How many people attended? Ten members and creators joined the full curated weekend, while broader community events—like the Saturday Pilates class and Sunday tennis clinic—each drew 30 singles.
What kind of activities were included? A HIIT Pilates class with Madison Appel and lululemon, a “Doubles for Singles” tennis clinic with Madison Appel, breakfast and lunch gatherings, a Wimbledon Finals watch party, and evening events at Surf Lodge.
Is this a one-time event? No. This was the first of three Hamptons weekends The League is hosting this summer, with additional weekends coming in the following weeks and at the end of August.
The League is built for people who approach dating this way — seriously, honestly, and with a real sense of what they’re looking for. Learn more about how The League works.