Long Island's South Shore, curated weekly
This weekend in Sayville (August 13 to 15): Sayville International Film Festival at Sayville Theater (Thursday); Ferragosto on the Farm at Loughlin Vineyard (Saturday 12:00PM); Shakespeare in the Park: A Midsummer Night's Dream at Long Island Maritime Museum (Thursday 6:00PM), plus 3 more picks below.
Events for the weekend of August 13 to 15, 2026
Every week we read through everything happening across the South Shore and keep only what is actually worth your time. Here is what is on in Sayville this weekend.
This Weekend's Top Picks in Sayville: Sayville International Film Festival at Sayville Theater (Thursday).
The inaugural SIFF brings four days of independent cinema, filmmaker Q&As, and a red-carpet awards night to Main Street: screenings at the Sayville Theater, closing gala at CM Performing Arts Center; single-block tickets $15, full pass $125.
For Families in Sayville this weekend: Ferragosto on the Farm at Loughlin Vineyard (Saturday 12:00PM); Shakespeare in the Park: A Midsummer Night's Dream at Long Island Maritime Museum (Thursday 6:00PM).
An Italian late-summer festival on the vineyard lawn: watermelon dishes and spritzes, lawn games, and live music by Evan & James 2-5 PM; the vineyard's own invite says bring family and friends.
Islip Arts Council and Studio Theatre of Long Island's fully costumed free outdoor Midsummer on the maritime museum grounds, a warm summer-evening pick for all ages.
Date Night & Nightlife in Sayville this weekend: Vine & Vegetable: Just Peachy at Loughlin Vineyard (Friday 12:00PM).
A peach-season vineyard afternoon: a one-day menu by Chef Sal of Orchard Street, fresh Great South Bay oysters from Tall Mutha Shucka, and music by Paris Ray 4:30-7:30 PM.
Free & Affordable in Sayville this weekend: Kevin Hart (Live Music) at The Cull House (Thursday 6:00PM).
Waterfront live music at Sayville's seafood spot.
Also Happening This Weekend in Sayville: Trivia Night at the Vineyard Hosted by Tango Time at Loughlin Vineyard (Thursday 6:00PM).
A relaxed vineyard trivia night with wine and friendly competition.
This is the short version. The full South Shore Digest, with the five things actually worth your weekend and a first-person take on a local spot we visited that week, lands in your inbox every Thursday. It is free, and it is the easiest way to never miss a good night out on the South Shore.
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