Long Island's South Shore, curated weekly
This weekend in Sayville (October 15 to 18): Oktoberfest in the Vines at Loughlin Vineyard (Sunday 12:00PM); Haunted Teen Central at Sayville Library (Thursday 5:30PM); Deanna Hudson at The Cull House (Thursday 5:00PM), plus 6 more picks below.
Events for the weekend of October 15 to 18, 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: Oktoberfest in the Vines at Loughlin Vineyard (Sunday 12:00PM).
Loughlin Vineyard holds Oktoberfest in the vines from noon to 6, with live German music from Smorgasband from 1 to 4, a German-inspired menu from Orchard Street and German beers alongside the estate wines. The vineyard recommends reservations and will take a limited number of walk-ins.
For Families in Sayville this weekend: Haunted Teen Central at Sayville Library (Thursday 5:30PM).
The library's teen department turns its rooms into a haunted house with ghosts, aliens and zombies, in two versions: a Not Scary walk-through (Thursday and Friday 5:30 to 6:30, Saturday 2 to 4 and 5:30 to 6:30) and a Scary one with live performers (7 to 8 each night). Bring one nonperishable item per person for the library's Little Free Food Pantry or Pet Pantry.
Free & Affordable in Sayville this weekend: Deanna Hudson at The Cull House (Thursday 5:00PM).
Deanna Hudson plays The Cull House in Sayville, 5 to 8.
Around the Community in Sayville this weekend: Bayport-Blue Point Chamber of Commerce 2026 Community Expo; Islip Apple Festival Scarecrow Contest + Taste of Apple Culinary Contest at Sayville.
The Bayport-Blue Point Chamber sets up its Community Expo at Bayport Flower Houses on October 21, 4 to 8 PM, a chance to meet local businesses around kids activities, food trucks, a fire safety demo, live entertainment and a gift basket raffle.
The Town of Islip Apple Festival runs two contests at the Islip Grange, open to all ages. Scarecrows come in with the entry form Friday Oct 23 between 9 AM and 3 PM or Saturday Oct 24 from 8 to 9:30 AM, while homemade pies, cakes, breads, jams and cookies for the Taste of Apple Culinary Contest are due at the Grange by 10:30 AM on Oct 24; call 631-224-5430 for info.
Also Happening This Weekend in Sayville: Trivia Night at the Vineyard Hosted by Tango Time at Loughlin Vineyard (Thursday 6:00PM); Vine & Vegetable #004: How 'Bout Them Apples at Loughlin Vineyard (Friday 12:00PM); Sayville Falls Fall Concert Series: Renee D'Angelo at Sayville Falls Beer Garden (Friday 5:30PM).
A vineyard trivia night in Sayville.
A seasonal apple-themed food-and-wine afternoon at the vineyard.
An outdoor beer-garden concert, 5:30 to 8:30, on a wet-forecast Friday with no rain plan posted. [IG-ONLY: re-open at Gate 1].
A beer-garden concert in Sayville. [IG-ONLY: re-open at Gate 1].
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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