The Sag Harbor Chamber of Commerce has held its annual Halloween Pumpkin Trail for more than 40 years. The first village to offer an opportunity for children to “trick-or-treat” at local businesses, Sag Harbor’s Pumpkin Trail idea soon spread to other villages and areas on the East End. The Pumpkin Trail has become a Sag Harbor tradition everyone looks forward to, with youngsters invited every Halloween to make Sag Harbor’s business district a stop on their trick-or-treat trail.
All children dressed in Halloween costumes can look for Chamber member businesses with a Sag Harbor Chamber Pumpkin Trail sign in their window — an invitation to stop by for some treats — no tricks required!
When Halloween falls on a weekday, the Pumpkin Trail runs from 3 to 5 p.m. When it falls on a weekend, the hours are 1:30 to 3:30 p.m.
If you are a member and Main Street business owner, let us know if you’d like to participate. Just send us an email at president@sagharborchamber.com, and we’ll make sure you get signage for your window.
SUNDAY, OCTOBER 26 – SUNDAY, NOVEMBER 2
Sunday, October 26th, 2025 | 2 PM – 4 PM Kids Spooky Creativity Lab at The Church
Friday, October 31st, 2025 | 4PM – 6PM
Red Carpet Dance Party with Scary-oke at Bay Street Theater
Saturday, November 1st or Sunday, November 2nd, 2025 | 11:00 AM
A matinee screening of Monster House at The Sag Harbor Cinema w/free popcorn
PLUS a 25% discount at Cluckman’s and 10% off at Page
TICKETS: SPOOKYPALOOZA PASS: $30 per person; includes all 3 activities and food discounts Over a $20 Savings!
Available through Sag Harbor Cinema
Tickets to individual events at The Church and Bay Street Theater
will only be available on the day of the event at the door of the institution – capacity permitting. Individual Tickets will be $15 per person. A la carte tickets do not include restaurant discounts
All children must be accompanied by an adult
