Long Island's South Shore, curated weekly

Things to Do in Sayville This Weekend

This weekend in Sayville (October 1 to 4): Cassidy Lee at The Cull House (Thursday 5:00PM); Sayville Falls Fall Concert Series: Deanna Hudson at Sayville Falls Beer Garden (Friday 5:30PM); Sunday Sounds with High Note and Orchard Street at Loughlin Vineyard (Sunday 12:00PM), plus 6 more picks below.

Events for the weekend of October 1 to 4, 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.

Free & Affordable

Free & Affordable in Sayville this weekend: Cassidy Lee at The Cull House (Thursday 5:00PM); Sayville Falls Fall Concert Series: Deanna Hudson at Sayville Falls Beer Garden (Friday 5:30PM); Sunday Sounds with High Note and Orchard Street at Loughlin Vineyard (Sunday 12:00PM).

Cassidy Lee

Thursday, October 1, 5:00PM  |  The Cull House, Sayville

Waterfront live music at Sayville's seafood spot, 5 to 8.

Sayville Falls Fall Concert Series: Deanna Hudson

Friday, October 2, 5:30PM  |  Sayville Falls Beer Garden

The beer garden's fall concert series continues Friday evening, 5:30 to 8:30.

Sunday Sounds with High Note and Orchard Street

Sunday, October 4, 12:00PM  |  Loughlin Vineyard, Sayville

Live music and Orchard Street food among the vines, noon to 6.

Around the Community

Around the Community in Sayville this weekend: Bayport-Blue Point SEED Welcome Back Fundraiser; Sayville Library Haunted Teen Central Donation Call.

Bayport-Blue Point SEED Welcome Back Fundraiser

Bayport

Register by Friday for a free raffle ticket to the SEED Foundation's Welcome Back fundraiser, held at People's Pub in Bayport the following Thursday evening.

Sayville Library Haunted Teen Central Donation Call

Sayville

The library's teen haunted house, coming in mid-October, is collecting a tricycle, vintage luggage, a nightstand, white towels and sheets, and lacy curtains in clean, good condition; contact the Sayville Library to drop off.

Also Happening This Weekend

Also Happening This Weekend in Sayville: Friday Fall Feast featuring Orchard Street and Johnny Kroo at Loughlin Vineyard (Friday 12:00PM); Sayville Falls Fall Concert Series: Joseph Powers at Sayville Falls Beer Garden (Saturday 5:30PM); Saturday Sounds with Paris Ray, Oysters by Tall Mutha Shucka and Food by Orchard Street at Loughlin Vineyard (Saturday 12:00PM).

Friday Fall Feast featuring Orchard Street and Johnny Kroo

Friday, October 2, 12:00PM  |  Loughlin Vineyard, Sayville

Wine, live music and Orchard Street food, noon to 8.

Sayville Falls Fall Concert Series: Joseph Powers

Saturday, October 3, 5:30PM  |  Sayville Falls Beer Garden

Saturday-evening set in the beer garden's fall series.

Saturday Sounds with Paris Ray, Oysters by Tall Mutha Shucka and Food by Orchard Street

Saturday, October 3, 12:00PM  |  Loughlin Vineyard, Sayville

Live music, oysters and Orchard Street food among the vines.

Trivia Night at the Vineyard Hosted by Tango Time

Thursday, October 1, 6:00PM  |  Loughlin Vineyard, Sayville

Team trivia at the vineyard.