The Sag Harbor Chamber of Commerce has one simple timing rule for its Halloween Pumpkin Trail. When Halloween falls on a weekday, the trail runs from 3 to 5 p.m. When it falls on a weekend, it runs from 1:30 to 3:30 p.m. This year Halloween is on Saturday, October 31, so the Chamber's weekend hours apply. The East End Getaway calendar lists the 2026 trail for October 31 at those weekend hours.
On a weekday Halloween, trick-or-treating on Main Street is something families fit in after school. On a Saturday it sits in the middle of the day, and the rest of the village's programming, from the farmers market to the library, the cinema and Bay Street Theater, falls in before or after it. Read in order, the weekend calendar runs as one continuous day.
The two hours everything else lines up around
The Pumpkin Trail has been running for more than 40 years. The Chamber describes Sag Harbor as the first village to invite children to trick-or-treat at local businesses, an idea that later spread to other villages and areas on the East End. The setup is simple. Children in costume look for Chamber member businesses with a Sag Harbor Chamber Pumpkin Trail sign in the window, and each sign means a stop for treats.
Bay Street Theater's "S'mores and Scares!" spooky story staged reading runs from 12:30 to 1:30 p.m. on October 31. According to the Spooky-Palooza listing, the hour includes campfire tales, red-carpet costume photos with the young performers, and a first goody bag of Halloween and campfire treats "before you head off to Trick or Treat down the Pumpkin Trail." The reading ends at 1:30 p.m., the same minute the trail opens. Tickets for the reading are $15 per person.
Saturday, hour by hour
| Time | What | Where |
|---|---|---|
| 9 a.m. to 1 p.m. | Final listed Saturday of the 2026 farmers market | Bay and Burke, in front of Breakwater Yacht Club |
| 11 a.m. to noon | Boo Bash for ages birth to 5, registration required | John Jermain Memorial Library; confirm format on the event page |
| 11 a.m. | Frankenweenie family matinee with complimentary popcorn | Sag Harbor Cinema |
| 12:30 to 1:30 p.m. | S'mores and Scares! staged reading | Bay Street Theater |
| 1:30 to 3:30 p.m. | Halloween Pumpkin Trail | Chamber member businesses with the trail sign |
| 6 p.m. | Frankenstein with a live guitar score by Gary Lucas | Sag Harbor Cinema |
| 8 p.m. | The Rocky Horror Picture Show | Bay Street Theater |
The morning is for the youngest costumes
The day starts at the water. The Sag Harbor Farmers Market lists its 2026 season as Saturdays from May 23 through October 31, 9 a.m. to 1 p.m., at Bay and Burke in front of Breakwater Yacht Club. That makes Halloween the last listed market Saturday of the year. The vendor roster includes Mecox Bay Dairy, Eel Town Oysters, Feathertop Farm, Newlight Breadworks, Stone's Throw Farm, Javier's Empanadas and South Fork Bakery, so the morning is the last chance to stock up from these vendors at the market before November. Like every listing in this post, the schedule can change, so check with the organizers before heading out.
While the market is still open, the John Jermain Memorial Library holds its Boo Bash, a costume dance party for children from birth to age 5, from 11 a.m. to noon. The listing names the Lower Level Program Room, but it also includes a note about online access, so check the format when you register. Registration is required and seats are limited. Also at 11 a.m., Sag Harbor Cinema shows Frankenweenie as a Kids and Families Matinee. The Spooky-Palooza listing adds complimentary popcorn with the screening.
So the morning gives three options for a family with small children, all wrapping up at about the time the S'mores and Scares crowd is gathering at Bay Street, and all done before the trail opens.
After dark, the schedule turns toward adults
After the trail closes at 3:30 p.m., the programming changes audience. At 6 p.m., Sag Harbor Cinema screens James Whale's 1931 Frankenstein while guitarist Gary Lucas performs a live solo score. The Spooky-Palooza page describes the performance as a mix of composed themes and "wild flights of improvisational sonic wizardry," played along with the film. The cinema's ticketing page lists $18.55 for adults, $15.50 for seniors 60 and over, $15.50 for people with disabilities, and $14 for youth 12 and under, plus a $2 fee per ticket.
At 8 p.m., Bay Street Theater screens The Rocky Horror Picture Show as an interactive night with costumes, a fully stocked bar and shouting at the screen, presented in tribute to the late Tim Curry. Tickets are $25.99 for one or $40.99 for two. Both evening screenings tie back to the morning. Frankenweenie is a family take on the Frankenstein story, and Frankenstein plays at the same cinema a few hours later. Families get the matinee version, and adults get the 1931 original with live music.
Friday opens the weekend, Sunday closes it
Saturday is the center of a three-day event. This is the third annual Spooky-Palooza, presented together by Sag Harbor Cinema, The Church and Bay Street Theater from Friday, October 30, through Sunday, November 1.
New this year, the three organizations are hosting a Spooky-Palooza Dance Party and Costume Contest at The Church, 48 Madison Street, on Friday from 6 to 9 p.m. Tickets are $90 each, or $75 per person for groups of two or more. The Church's event page lists complimentary food tables, a cash bar, a set from DJ Henry Eau, and a grand prize for the best costume. Each ticket holder also gets one complimentary spooky spritzer at Sag Harbor Cinema's Green Room, before or after the party. All proceeds go to The Church, Bay Street Theater and Sag Harbor Cinema. The community sponsors listed are Cluckman's, Page, Harbor Market, Lulu, Kidd Squid, Sen and Faraway.
Sunday is quieter. Frankenweenie plays again at 11 a.m. at the cinema for families who missed Saturday. From noon to 2 p.m., The Church hosts the Fall Fun Creativity Lab, with blank canvases, ceramic sugar skulls and fall coloring pages to take home. Tickets are $15 per person for all ages. The Church's description notes that "each year we witness the adults having just as much fun as the kiddos."
Weekend checklist:
- Friday, 6 to 9 p.m. Dance party and costume contest at The Church
- Saturday, 9 a.m. to 8 p.m. start times Market, library, cinema, Bay Street and the Pumpkin Trail, in that order
- Sunday, 11 a.m. to 2 p.m. Second Frankenweenie matinee, then the Creativity Lab
What Main Street looks like once the market is gone
After Halloween weekend, the market's Saturday mornings at Bay and Burke end for the season, and Main Street's year-round businesses carry more of the routine. One of the newest is at the head of the street. Cruust, a sandwich shop, opened July 14 at 2 Main Street, replacing Espresso da Asporto as a year-round business. General manager Bobby Deery told 27east the concept was created "with the local in mind," with sandwiches, pasta, salads and coffee on the menu and a plan to keep serving locals through the winter.
Next door, The Corner at 1 Main Street is still closed. Spark Hamptons reported on October 15 that the original restaurant operators had withdrawn and the property owners are looking for a new operator for a year-round restaurant. No replacement or opening date has been announced.
The same organizations behind Spooky-Palooza also have November on the calendar. Bay Street Theater stages Harper Lee's To Kill a Mockingbird from November 9 through 29 as part of its Literature Live! series. The Church's sixth annual Holiday Makers Market returns to 48 Madison Street on Saturday, November 28, and Sunday, November 29, from 11 a.m. to 4 p.m. each day. It will have more than 20 makers and a new Creativity Lab, with admission of $5 per day and free entry for children under 12.
I love weekends like this one, when Sag Harbor puts its whole calendar on the street at once. If you'd like to talk about the village beyond Halloween, from which corners stay busy all winter to what's changing on Main Street, Dawn Watson is always glad to compare notes. Connect with Dawn to start your Hamptons search.
