Sign up for our Newsletter

(Photo by Jeremy Garretson)

The first full month of autumn is upon us. From frights to fall fun, here are some of the things we are most excited to do this October. 

Skate into Art

In this showcase of art and high-flying performances, the second annual Sound & Skate Festival returns to Greenport on Saturday, Oct. 7 at the Greenport Skate Park on Moores Lane. From 11 a.m. to 6 p.m., you can watch skating and BMX bike demonstrations, see a live painting showcase, munch on local snacks, shop over 50 vendors and support the local skating culture. Come celebrate the community while shedding light on the necessary fundraising efforts to build a safer and more enticing park for all ages and skate disciplines. This is a free festival and updates can be found here.

Run Through the Vines

Enjoy Pindar Vineyards as you never have before with this scenic autumn footrace scheduled for Sunday, October 1. Run through 300 acres of vines during the most beautiful time of the year. This family-friendly event, which kicks off at 9 a.m., includes a 5K walk/run for $45 an 8K race for $50, and a post-run party featuring live music, the Royal Elite BBQ food truck and plenty of wine. Proceeds will support the NY Cancer Foundation. Advance registration is required online.

Help with the Harvest

On Sunday, Oct. 15, experience winemaking right from the beginning during RGNY’s annual Help Us Harvest event. From 11 a.m. to 2 p.m., the vineyard will offer the unique firsthand experience of harvesting grapes from this year’s crop and teach you how to clip and sort grapes as you learn about the winemaking process. Tickets for this event are $90 per adult and include a glass of sparkling wine upon arrival, a tranquil lunch, two more glasses of wine and educational sessions with both RGNY’s winemaker and viticulturist while they harvest and sort grapes alongside you. You can purchase tickets in advance here

Celebrate Spooky Season in Downtown Riverhead

 October is the most wonderful time of the year for Downtown Riverhead, where the streets are decked out with goblins and ghouls and lampposts are wrapped with fall-themed and Halloween decor. On Saturday, Oct. 21, dress the whole family in costume to join the local community for a day of spooktacular surprises. Coffin races, trick or treating for the kids and a Halloween parade are all on this year’s schedule. Head to their website for more information. 

Halloween Hijinks at the Aquarium

All October long, The Long Island Aquarium offers numerous fun-filled events for the whole family. Every Friday and Saturday starting Oct. 6 through the 28, explore the Aquarium’s Haunted Tree House, a not-so-scary immersive experience where you can walk through five levels of Halloween fun. $25 per person and $20 for members. Then, on Saturday, Oct. 28, celebrate the holiday with Bats, Barnacles & Broomsticks – a Halloween Party.  All “buoys” and “ghouls” in costume will get 50% off aquarium admission ($45.99 for adults, $32.99 for seniors, children 3-12 $31.99 and children 2 and under are free) with a paying adult. Find more information here

Cheers to the Almighty Oyster

Oyster Fest returns to Greenport Harbor Brewing Co. on Sunday, Oct. 8. From noon to 6 p.m., head to their Greenport Village location to shuck local oysters and taste their Unhinged Oyster Stout on tap (a collaboration with Little Creek Oysters). Live funky, fun music by New Life Crisis will be performed from 1:30 to 5:00 p.m. Find more info here

Wine by the Vines

Celebrate 50 years of Long Island Wine with Southold Historical Museum and Pellegrini Vineyards in Cutchogue. On Thursday, Oct. 19 from noon to 3 p.m. taste fine wine and delectable food. Enjoy an autumn afternoon with family, friends, and neighbors while supporting The Southold Historical Museum. New to Wine by the Vines this year is North Fork Bingo – which will feature questions about Long Island’s wine history. Come test your knowledge and win big. Tickets are $60 per person and include Bingo. Find more information and purchase in advance here

Watch the Game with Friends 

Every Sunday beginning Oct. 1, Corey Creek Tap Room will host Gameday Sundays, From noon to 5 p.m., guests can enjoy football while noshing on local pretzels and sipping on their small-batch wines. There will also be live music and fresh oysters from Harvest Moon Shellfish Co. A glass of Dogs Day Riesling Shandy and a locally baked pretzel from New Light Breadworks will be available for $10. 

Boo-tastic Barn Dance

Celebrate Halloween with a classic country barn dance. On Saturday, Oct. 28 at 7:30 p.m. suit up in your cowboy boots or your best costume and head to Spirits Promise in Riverhead to dance the night away. There will be a prize for the best costume. BYO snacks and drinks. Tickets, are $15 per person and can be purchased here.  

Snuggle up with some S’mores

As the days grow chillier, cozy up around a personal bonfire for an evening of marshmallow roasting and port sipping at North Fork Table & Inn. Available every Wednesday through Sunday beginning September 27, this s’mores kit for two will be available for purchase for $60. The kit will include locally sourced ginger snap cookies, marshmallows, and chocolate, along with your choice of port or house-made hot chocolate. Reservations are encouraged and can be made here