Long Island's South Shore, curated weekly

Things to Do in Islip This Weekend

This weekend in Islip (October 8 to 11): Annual Oktoberfest at the Snapper Inn (Sunday 1:00PM); Spookley the Square Pumpkin, the Musical at CM Performing Arts Center (Saturday 10:00AM); Live Music by Dudes Acoustic at Oakdale Brew House (Friday 7:00PM), plus 4 more picks below.

Events for the weekend of October 8 to 11, 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 Islip this weekend.

This Weekend's Top Picks

This Weekend's Top Picks in Islip: Annual Oktoberfest at the Snapper Inn (Sunday 1:00PM).

Annual Oktoberfest at the Snapper Inn

Sunday, October 11, 1:00PM  |  Snapper Inn, Oakdale  |  $

The Snapper Inn's annual Oktoberfest on the Connetquot River, 1 to 5: German food, music and a beer garden on the water.

For Families

For Families in Islip this weekend: Spookley the Square Pumpkin, the Musical at CM Performing Arts Center (Saturday 10:00AM).

Spookley the Square Pumpkin, the Musical

Saturday, October 10, 10:00AM  |  CM Performing Arts Center, Oakdale  |  $$

Opening weekend of CMPAC's children's musical about a pumpkin who learns that being different makes him special, rated G, about an hour and 25 minutes with intermission. Sunday's 11 AM show is a sensory-sensitive performance.

Free & Affordable

Free & Affordable in Islip this weekend: Live Music by Dudes Acoustic at Oakdale Brew House (Friday 7:00PM).

Live Music by Dudes Acoustic

Friday, October 9, 7:00PM  |  Oakdale Brew House

Dudes Acoustic plays the Oakdale Brew House on Friday, 7 to 10.

Also Happening This Weekend

Also Happening This Weekend in Islip: Blind Taste Test at Islip Public Library (Thursday 6:00PM); Halloween Paint Night at Islip Public Library (Thursday 6:30PM); Books & Brews at Oakdale Brew House (Saturday 12:00PM).

Blind Taste Test

Thursday, October 8, 6:00PM  |  Islip Public Library  |  Free

A playful blind-tasting game night at the Islip Library.

Halloween Paint Night

Thursday, October 8, 6:30PM  |  Islip Public Library  |  Free

A spooky-themed guided paint night at the Islip Library.

Books & Brews

Saturday, October 10, 12:00PM  |  Oakdale Brew House  |  Free

A relaxed book-club gathering over craft beer at the Oakdale brewhouse.

Klezmer Concert (Oakdale)

Sunday, October 11, 2:00PM  |  B'Nai Israel Reform Temple, Oakdale

The Islip Arts Council presents a klezmer concert with David Gluck at B'Nai Israel Reform Temple, suggested donation at the door. [Link](.