Top 10 East End Outdoor Events This Week: October 16–22, 2020

Three cute little puppy dogs dressed in Halloween costumes sitting in a field at night
Tails will wag at this year’s spooky Wag-O-Ween party, Photo: 123RF

There’s a great deal to do and see on the East End this week, with several exhilarating outdoor events you don’t want to miss. This week’s top happenings include a TV pilot drive-in festival, a Halloween party for our furry companions and more!

North Fork TV Festival
Saturday, October 17, 5:30 p.m.

The annual festival comes to Castello di Borghese Vineyard with exclusive drive-in pilot screenings, creator conversations, an award ceremony honoring Jeremy Sisto, bites and drinks from local eateries and wineries, live music and more. 17150 County Road 48, Cutchogue.

Forest to Salt Marsh Walk
Sunday, October 18, 10:30 a.m.

Join South Fork Natural History Museum Education & Outreach Coordinator Melanie Meade for a 1.5-mile walk along a Greenport trail that winds through shrublands and an old oak forest, ending with stunning views of the Long Island Sound. Register for meeting place. 631-537-9735,

RG|NY Harvest Weekend
Sunday, October 18, 11 a.m.–4 p.m.

Guests will receive their own “harvest gear” as winemaker Lilia Perez guides them through an exclusive look into winemaking process. Tickets are $85 and include lunch from Lombardi’s Love Lane Market and a bottle of 2018 Scielo Roseì. 6025 Sound Avenue, Northville.

Sunday, October 18, 1 p.m.

Southampton Animal Shelter Foundation’s Spooktacular is “bark” again with a Doggie Costume Parade and a Howloween Photo Booth. Email [email protected] to register. 102 Old Riverhead Road West, Hampton Bays,

Gather Outdoor Screening
Sunday, October 18, 6 p.m.

This documentary follows the stories of natives on the frontlines of a growing movement to reconnect with spiritual and cultural identities that were devastated by genocide. Tickets to the Southampton Arts Center screening are $15 but free to members of the Shinnecock Nation. 25 Jobs Lane, Southampton.

CTREE Fall Open House
October 19–22, 5 p.m.

Celebrate a decade of serving the special needs community of the East End by watching therapeutic riding lessons and meeting the CTREE horses. 93 Merchants Path, Sagaponack. 631-779-2835,

Shelter Island 5K Run/Walk
October 17–26.

Virtual participants can walk or run any 5K and submit times through October 26. All race proceeds support the North Fork Breast Health Coalition, the Coalition for Women’s Cancers at Stony Brook Southampton Hospital and Lucia’s Angels.

Private Guided Wine Country Tour
Monday–Friday, 10 a.m.–3 p.m.

Long Island Bike Tours take your group of up to six people on an intimate and private tour experience through the bucolic North Fork.

Book Sale on the Bricks
Saturdays through October 30, 11 a.m.–2 p.m.

Books in boxes will be rolled outside Cutchogue New Suffolk Free Library on to the bricks for your perusal, delight, delectation and purchase. 27550 Main Road, Cutchogue. 631-734-6360,

The Maize at Fairview Farm
Now through November 8, 10 a.m.–6 p.m.

Fairview Farm at Mecox’s popular corn maze returns for its 20th year with an all-new design, featuring an easy route and a much more challenge path through eight acres of winding paths through 10-feet-tall corn. 19 Horsemill Lane, Bridgehampton. 631-537-6154,

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

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