Chloe Caillet & Kaytranada at The Surf Lodge
When: Saturday, May 24th, 2025
Doors Open at 4pm
Where: The Surf Lodge, 183 Edgemere St, Montauk, NY
Kick off Memorial Day Weekend at the iconic Surf Lodge!
known for great bites, great drinks, and even better live music.
SlowFires NYC x Ruschmeyers Pizza Pop-Up
When: Fri, May 23rd- Sat, May 24th, 2025
4pm – 9pm
Where: Ruschmeyers, 161 2nd House Rd, Montauk, NY
A pizza pop-up like no other from Chef Justin Smillie and the SlowFires team, the team will be serving up wood-fired pizzas with slow-fermented dough and seasonal toppings like ramps, black truffles and more!
Dolce Vita Pop-Up in Southampton
When: Fri, May 23rd- Sun, May 25th, 2025
11am – 3pm
Where: Dolce Vita, 95 Main Street, Southampton, NY
Beloved footwear brand Dolce Vita is partnering with Down the Street on a Summer Art Series, featuring three distinct monthly art drops each launched with a store event weekend where guests can view the newest collection, shop, and enjoy seasonal perks.

Lands’ End x Round Swamp Farm
When: Fri, May 23rd- Sat, May 24th, 2025
8:30am – 6pm
Where: Round Swamp MTK – 71 S Elmwood Ave, Montauk, NY
Round Swamp BH- 97 School Street, Bridgehampton, NY
From May 23-24, customers who visit Round Swamp Farm’s Amagansett or Montauk locations can receive this custom tote with any purchase over $200 (limited one tote per customer).
Hello Brooklyn
at The Stephen Talkhouse
When: Saturday, May 24th, 2025
10:30pm
Where: The Stephen Talkhouse, 161 Main St, Amagansett, NY
It’s not a true weekend in the Hamptons without hitting up the Stephen Talkhouse!
Known for their live entertainment, grab a Talkhouse Encore and jam out to Hello Brooklyn!
Levain Bakery X John’s Drive-In
When: Beginning May 23rd, 2025
8am – 5pm
Where: Levain Bakery, 354 Montauk Hwy Wainscott, NY
For a limited time, the iconic bakery is teaming up with John’s Drive-In!
Levain’s thick, gooey cookies with delicious scoops for a next-level summer treat.
Silent Disco Dance Party in the Garden
When: Sunday, May 25th, 2025
8pm – 11pm
Where: Guild Hall, 158 Main St, East Hampton, NY
DJ’s Mister Lama (Carlos Lama), ZiggaSun (Almond Zigmund), and Sits-a-Lot (Amy Kirwin) are back to spin your favorite tunes from disco to funk, 80s and 90s hip-hop and rap, and pop hits from all decades!
NOTD at The Clubhouse Hamptons
When: Saturday, May 24th, 2025
9pm – 2am
Where: The Clubhouse Hamptons, 174 Daniels Hole Rd, East Hampton, NY
NOTD live at the Clubhouse Hamptons, presented by Rose Gold.

Kites for Kids Benefit at Main Beach
When: Saturday, May 24th, 2025
2pm – 5pm
Where: Main Beach, 101 Ocean Ave, East Hampton, NY
Buy a kite –Deck it out with stickers, ribbons, glitter, and markers at the kite decorating station –Let it fly!
All proceeds will benefit the Eleanor Whitmore Early Childhood Center.
Jon Divello at Kidd Squid
When: Sunday, May 25th, 2025
5pm – 7pm
Where: Kidd Squid, 11 Spring St, Sag Harbor, NY
Enjoy the weekend with a fresh IPA and live music at a local hotspot, Kidd Squid.
They’re constantly whipping up new brews, and stock non-alcoholic options too.
Garden Club of East Hampton’s Garden Party
When: Friday, May 23rd, 2025
6pm – 8pm
Where: Mulford Farm, 10 James Lane, East Hampton, NY
The festive party features an extensive Silent Auction, which includes everything from vacation rentals to art, books, and luxury items donated by local retailers. Delicious hors d’oeuvres and beverages will be served.

Jenni Kayne’s Hamptons Kickoff
Join Jenni Kayne as they celebrate the unofficial start of summer with a weekend full of fun, drinks, and in-store festivities.
RSVP Required
Amagansett Store – Friday, May 23
10 Amagansett Square Drive, Amagansett, NY
2pm-5pm
• Oyster Bliss shucked oysters
• LALO Tequila Bar & Nomadica Wine
• Custom embroidery
• Florals by Topiaire I While Supplies Last
• A pop-up farmers market experience
RSVP: [email protected]
Amagansett Store – Sunday, May 25
10 Amagansett Square Drive, Amagansett, NY
• Yoga class with 11938 Fitness Inc I 9am – 10am
• Pet portraits by Rachel Hearn I 11am – 3pm
• NATUROPATHICA mini massages I 10am – 12pm
RSVP: [email protected]
Southampton Store – Saturday, May 24
2pm – 5pm
2 Main St Unit B, Southampton, NY 11968
• Mini lobster rolls & crudité from Bostwick’s
• LALO Tequila Bar & Nomadica Wine
• Live saxophone music
• Floral bundles by Topiaire I While Supplies Last
RSVP: [email protected]
Southampton Store – Sunday, May 25
2 Main St Unit B, Southampton, NY 11968
• Yoga Sculpt class with Wave Wellness I 9am – 10am
• Mini facials by Shou Sugi Ban House I 10am – 1pm
RSVP: [email protected]
Southampton Artists Association 2025 Memorial Day Art Exhibit
When: Thurs, May 22nd – June 1st, 2025
MON-THURS 12-4 FRI 12-6 SAT 10-6 SUN
Where: Southampton Cultural Center, 25 Pond Lane, Southampton, NY
Check out local artists’ work—various creations in different artistic mediums!