FRIDAY
Greenport Express Halloween Spooktacular | Greenport Express Miniature Railroad, Moore’s Lane, Greenport
Take a spooky train ride where ghosts, goblins and glowing pumpkins come alive along the tracks from 4-9 p.m. Tickets are $10 per ride, or $9 for guests wearing costumes on Oct. 30 only. Tickets are available on the day of the event only. For details, look here.
Shelter Island Annual Parade and Trunk or Treat | Duvall Street, Shelter Island
Gather in the parking lot next to the public tennis courts on Duvall Street for the Parent Teacher Student Association’s annual Trunk or Treat extravaganza from 4-7 p.m. To sign up to be a grown-up, four-wheeled candy corraller, contact Barbara Marshall at 631-599-8957.
SATURDAY
Greenport Village Halloween Parade & Celebration | Mitchell Park, 115 Front Street, Greenport, 631-477-2200
The annual Greenport Village Halloween Parade heads from Floyd Memorial Library to Mitchell Park; celebrate from 11:30 a.m.-5 p.m. with sweet treats and scary fun, including free carousel rides for kids under 12, spooky storytime and a showing of Hocus Pocus at the North Fork Arts Center. To learn more, look here.
Nightfaire on Sound Ave. Halloween Market | Jamesport Farm Brewery, 5873 Sound Ave., Riverhead, 631-779-2133
Browse a Halloween marketplace filled with handcrafted art, candles, jewelry, crystals and more from 11 a.m.-4 p.m. Explore the mystical with a tarot reading from tarot reader Peter while DJ Phil keeps the Halloween vibes going. Grab a bite from the food truck and sip on hauntingly good brews. For additional information, go here.
Paws & Pours Halloween Party | Bridge Lane Wine, 35 Cox Neck Road, Mattituck, 631-298-1942
Give Halloween a four-legged twist at Bridge Lane Wine’s Paws & Pours costume party from 2-5 p.m. Dogs are encouraged to arrive in their Halloween best, and owners of costumed pups receive a complimentary glass of wine. Expect a relaxed afternoon of socializing and photo opportunities. Dogs must be well-behaved and kept on a leash. For more details, click here.
Halloween Bash | Greenport Harbor Brewing Co., 42155 Main Road, Peconic, 631-477-1100
Celebrate Halloween from 7-11 p.m. with music, beer on tap, local wines, cocktails and food bites. Guests can also show off their Halloween looks in the costume contest, with categories for best individual, duo and group costumes. To learn more, go here.
SUNDAY
Halloween Candy and Wine Pairing | Clovis Point Vineyard & Winery, 1935 Main Road, Jamesport, 631-722-4222
Enjoy a special Halloween candy and wine pairing from 11 a.m.-6 p.m. featuring 2025 chardonnay paired with candy corn, 2024 sauvignon blanc paired with Skittles, 2022 cabernet franc paired with Snickers and 2021 merlot paired with peanut butter cups. This event is also on Oct. 31. Tickets are $35 per tasting. Call 631-722-4222 to reserve or email [email protected].
Lantern Walk | Orient Beach State Park, 40000 Main Road, Orient
Mark the end of Daylight Saving Time with a lantern walk hosted by the Friends of Orient Beach State Park from 4-5:30 p.m. Led by environmental educator Jen Murray, the walk begins in the main parking lot near the restrooms. Lanterns, hot chocolate and snacks will be provided. The event is free, donations are welcome and no vehicle parking fee is in effect. Recommended for children ages 6 and older, who must be accompanied by an adult. For more information, go here.
