Fun Things to Do on the North Fork, October 22–27, 2021

Enjoy roller skating in Greenport on the North Fork
Enjoy roller skating in Greenport!

The North Fork continues to be the East End’s greatest hub of activity this fall! Plan your week of fun things to do with live shows, outdoor events, art shows and more, October 22–27, 2021.


Zac Brown Tribute Band at Jamesport Farm Brewery
Friday, October 22, 1 p.m.

Fans of a little bit of “Chicken Fried” won’t want to miss their chance to hear this tribute band while sampling some excellent local craft beer. For a $5 admission fee, you can enjoy live music in the shaded beer garden and order drinks and tasty snacks off their lively American menu.
5873 Sound Avenue, Riverhead. 844-532-2337,

Ladies Night Wingo
Friday, October 22, 6:30 p.m.

Do you love bingo almost as much as you love wine? Round up the ladies and pay a visit to Terra Vite winery, where you’ll enjoy 15% off glasses and bottles while you play.
250 Manor Lane, Jamesport. 631-722-3416,

Acoustic Soul at Osprey’s Dominion
Saturday, October 23, 1 p.m.

No reservations are required for your chance to enjoy live classic rock hits while sipping on some of Long Island’s favorite bottles. Enjoy tables and umbrellas on the lawn and an upbeat vibe.
44075 Main Road, Peconic. 631-765-6188,

Erin Chase at Pindar Vineyards
Saturday, October 23, 1 p.m.

Enjoy live music under the pavilion with singer-songwriter Erin Chase. The winery is known for its young, lively atmosphere and a large selection of cheeses and crackers.
37645 Main Road, Peconic. 631-734-6200,

Freddy Monday at Clovis Point
Saturday, October 23, 1 p.m.

Don’t miss this singer-songwriter and multi-instrumentalist at one of North Fork’s favorite wineries. Clovis Point is known for its garden-like setting and excellent wines.
1935 NY-25, Laurel. 631-722-4222,

Dori Jo Guttierez at Jason’s Vineyard
Saturday, October 23, 1:30 p.m.

Don’t miss this native Long Islander performing live by the vines at Jason’s Vineyard. The venue is known for its well-priced tastings and quaint atmosphere.
1785 Main Road, Jamesport. 631-238-5801,

Adults 21+ Roller Skating in Greenport
Wednesday, October 26, 6 p.m.

Don’t skip your chance to show off your “wheelie” good skills Wednesday nights at the Greenport American Legion. You can rent a pair of skates, included in the $10 admission price, or purchase your own in the Pro Shop.
121 Third Street, Greenport.

Beading Group
Thursday, October 28, 12 p.m.

Do you love to craft? Don’t miss your chance to pop by and join this informal beading jewelry-making group. Registration is required and you should bring your own materials.
27550 Main Road, Cutchogue. 631-734-6364,

Borghese Vineyard's beautiful outdoor space, Photo: Allissa Goodale, ©Borghese Vineyard
General manager Evie Kahn overseeing Borghese Vineyard’s beautiful outdoor space, Photo: Allissa Goodale, ©Borghese Vineyard


Create a Jar for Fall
Saturday, October 23, 11 a.m.

Enjoy an afternoon at Downs Farm Preserve while you create a fairy jar for fall. The cost is $8 per person and children are welcome. Bring a blanket and snacks, but the event will be moved inside if the weather is inclement.
23800 Main Road, Cutchogue. 631-765-6450,

Saturday Tours at Borghese Vineyard
Saturday, October 23, 11 a.m., 1:30 p.m., or 3:30 p.m.

Call ahead to reserve a vineyard tour for a maximum of six people. Get your private tour of the vines, wine cellar and barrel hall. While you’re there, enjoy the highly-acclaimed wine selection and low-key vibe.
17150 Main Road, Cutchogue. 631-734-5111,

Bug Light Cruise & Tour
Saturday, October 23, 5 p.m.

Be sure to sign up ahead of time for this two-hour cruise and tour of the only lighthouse in the area that allows visitors. The tour itself is narrated by the great-grandson of the former keeper of the lighthouse.
103 Third Street, Greenport. 631-477-2100,

Classic Wine Country Tour
Saturday & Sunday, October 23 & 24, 10 a.m.

Enjoy a relaxing tour of the North Fork’s bucolic scenery with your friends and family. Packages include options like privileged access to vineyards, visits to local farm stands and wine tastings.
13200 Main Road, Mattituck. 631-871-1666,

Shelter Island 5K Virtual Race for Breast Cancer
Now through October 24

Don’t miss your last weekend to raise money for a good cause. Walkers and runners can register for $30 each and enter their times and photos through October 24. Meanwhile, enter for your chance to win gift cards to East End favorites such as Mimi Page Jewelry and Bostwick’s Restaurant.

[email protected], 631-774-9499,

Pumpkin Picking at Stakey’s Pumpkin Farm
Open Through October 30

Weekday fun includes pumpkin picking, hayrides and the corn maze, while weekend festivities add roasted corn, the snack shack, arm and hand painting, and more. The farm is open Monday through Friday, noon–5 p.m.; Saturday and Sunday,
9 a.m.–5 p.m.
270 West Lane, Aquebogue. 631-722-3467,

The title page from an antique book of the plays of Shakespeare
Dive into Shakespeare at an eye-opening virtual event this week.Getty Images


Shakespeare in Community Online
Saturday, October 23, 12:30 p.m.

Don’t miss your chance to discuss Shakespeare’s The Merry Wives of Windsor through Zoom. You can register online ahead of time through the Shelter Island Public Library.
37 North Ferry Road, Shelter Island. 631-749-0042,

Chair & Restorative Yoga
Monday, October 25, 10 a.m.

You won’t want to skip this hybrid event that can help you to reduce stress, increase flexibility and even lose weight. Register ahead of time for the Zoom info and bring your yoga mat and towel to your living room.
53705 Main Road, Southold. 631-765-2077,

It Came from the Sewers with Thomas Hynes
Wednesday, October 27, 6:30 p.m.

Thomas Hynes will be discussing his book about the tales of alligators in the New York City sewers and the real-life events that inspired the legend. Register ahead of time for the Zoom info.
13900 Main Road, Mattituck. 631-298-4134,

Art by Rasa Valiene at William Ris Gallery
Art by Rasa Valiene at William Ris GalleryCourtesy William Ris Gallery


Isadora, Rasa & Will with Ceramics by Bobbie & Bob Dalpiaz
Saturday, October 23, 4–7 p.m.

Don’t miss the opening reception and first glimpse at the paintings of artists Isadora Capraro, Rasa Valiene and Will Ryan. They represent different regions of the world and celebrate their interpretations of the universe. While you’re there, check out the sculptures of earthen work artisans Bobbie and Bob Dalpiaz. The exhibition runs through November 23.
1291 Main Road, Jamesport. 609-408-5203,

This Land Is Your Land
On view through October 30

Don’t miss your last week to view this collection of photos and paintings of historic Shelter Island. QR codes will be available to provide you with more information about each property, including how and when you can access them.
16 South Ferry Road, Shelter Island. 631-749-0025,

Fictional Narratives
On view through November 7

Explore themes like nostalgia, surrealism and transformation while you enjoy the still-lifes and photos by three thoughtful artists. Richard Aardsma, Laura Dodson and Marisa S. White have extensive experience creating and teaching about
25425 Main Road, Cutchogue. 631-723-8545,

Find more exciting Hamptons, North Fork and family events happening this weekend and beyond (or list your own event) at

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