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Spark Hamptons: Top Weekend Event Picks – What to Do Across the East End | May 14–17, 2026
From live music and comedy to art openings, film nights, and author conversations, here’s what’s happening across the Hamptons this week.
LIVE MUSIC + PERFORMANCE
Montauk Music Festival + Zebra Concert
Thursday, May 14 | 6:15–11:30 p.m.
Cost: Varies
Venue: Westlake Fish House, Montauk
In its 15th year, Montauk’s Music Festival turns up the music scene volume with a great energy, waterfront vibes, and live performances anchored by local 70s band favorite Zebra + a meet ‘n greet on Saturday.
Nancy Atlas with Jeremy Elliot Opening
Friday, May 15 | 7:30 p.m.
Cost: $50
Venue: The Stephen Talkhouse, Amagansett
A Hamptons music institution, Nancy Atlas delivers her signature East End rock-and-roll energy in a high-powered live set.
Jimmy Buffett Day
Saturday, May 16 | All day
Cost: No cover
Venue: The Clubhouse, East Hampton
Island time returns to the Hamptons for the third annual Jimmy Buffett Day celebration, featuring live sounds from The Big Revival Band, raffles benefiting Animal Rescue Fund of the Hamptons, food, drinks, and plenty of laid-back tropical vibes.
Jazz Night: “From Havana to Rio”
Friday, May 15 | Doors 6:30 p.m.
Cost: $20
Venue: Sag Harbor Masonic Temple
An intimate evening of Latin jazz and world-class musicianship inside one of Sag Harbor’s most atmospheric hidden gems.
Sticks & Stones Comedy Presents Vanessa Hollingshead
Saturday, May 16 | 8–9:30 p.m.
Cost: $35–$70
Venue: Southampton Cultural Center
Fearless, fast, and wildly funny, comedy veteran Vanessa Hollingshead headlines a sharp night of stand-up with feature comic Michele Fox.
Spring Varietal
Friday, May 15 | 6:30–8 p.m.
Saturday, May 16 | 2–3:30 p.m.
Cost: $17.50–$50
Venue: Guild Hall, East Hampton
East End youth performers showcase dance, theater, and musical talent in OFVS’s spring recital, featuring students across multiple age groups and disciplines.
ART + FILM
Late Night Studio Art Club
Wednesday, May 13 | 9 p.m.
Cost: Free
Venue: Ashawagh Hall, East Hampton
An open creative session for artists and makers of all levels. Bring your own supplies and join a relaxed, late-night community studio environment.
Film Night: Pasos, Directed by Bonny Melendez
Thursday, May 14 | 6 p.m.
Cost: Free
Venue: Ma’s House, Southampton
A lyrical experimental short exploring movement, memory, and cultural inheritance through the lens of traditional Peruvian Marinera dance.
Screening: Women Laughing — Women Cartoonists of The New Yorker
Friday, May 15 | 6–7:30 p.m.
Cost: $25
Venue: The Church, Sag Harbor
A witty, timely documentary spotlighting the women cartoonists who helped shape The New Yorker, followed by a live discussion and Q&A with filmmakers and contributors.
East End Women Group Exhibition
Saturday, May 16 | Noon–4 p.m. | Reception 4-6 p.m.
Cost: Free
Venue: Clinton Academy, East Hampton
A dynamic group exhibition curated by Karyn Mannix featuring 14 East End women artists working across mediums, with an opening reception from 4–6 p.m. Thru May 30.
Sip & Paint: Wisteria Vines With Lois Bender
Saturday, May 16 | 2–4 p.m.
Cost: $65
Venue: The Baker House 1650, East Hampton
Wine, watercolor, and spring garden inspiration come together for a relaxed, guided painting session in a historic East Hampton setting.
AUTHOR TALKS + CONVERSATIONS
Jeffrey Banks in Conversation With David Alpern
Friday, May 15 | 6–7 p.m.
Cost: Free
Venue: Rogers Memorial Library, Southampton
Fashion designer Jeffrey Banks reflects on his career and creative journey in a lively conversation spanning design, culture, and iconic figures in fashion history.
Author Talk & Book Signing: Dr. Elisa Port, Breast Advice – in Conversation with Christina Cuomo
Saturday, May 16 | 6–7:30 p.m.
Cost: Free
Venue: East Hampton Library
A leading breast surgeon offers essential, accessible guidance on breast health, from prevention and screening to treatment and emotional resilience. With Purist Magazine editor Christina Cuomo.
FAMILY + COMMUNITY
18th Annual Family Festival
May 14–17
Cost: $36.32–$46.72
Venue: Southampton Elks Lodge
A beloved community carnival featuring rides, games, food, and family entertainment, supporting local programs for youth, veterans, and community services.
Dog Social at The Shine Studio
Saturday, May 16 | 10 a.m.–2 p.m.
Cost: $40 per family
Venue: The Shine Studio
A playful, dog-friendly gathering with crafts for kids, snacks, and social time — benefiting Animal Rescue Fund of the Hamptons.
SPARK PICKS
If you only do a few things this weekend, we especially like: Montauk Music Festival, Women Cartoonists of the New Yorker at The Church, Vanessa Hollingshead at Sticks ‘n Stones Comedy Club and Jimmy Buffet Day at The Clubhouse.