Sag Harbor's Halloween this year runs for 16 days, from October 17 to November 1. Five local institutions run it. The Whaling Museum, the Masonic Lodge, the Chamber of Commerce, Bay Street Theater and Sag Harbor Cinema each take a different part of the month, often with a partner, and several of their events lead straight into the next one. One monster ties the schedule together. Mary Shelley's creature gets read aloud on a Saturday at noon. The next afternoon he's on screen at the Lodge, and a week later he's back at the Cinema with a live guitarist. The Hamptons International Film Festival is still showing films in the village through October 12. Once it ends, the village's own calendar takes over.
October 17: The Museum Goes First
The Sag Harbor Whaling and Historical Museum starts things off on Saturday, October 17, with its Haunted Walking Tour from 5:30 to 6:30 p.m. Annette Hinkle, a museum board member, leads it. The walk starts and ends at the museum and stops outside homes and businesses around Main Street. The museum describes it as a mix of local folklore and ghost stories passed along firsthand by residents and friends. Admission is $25. One adult is free with an individual membership, and two are free with a family membership.
The 2026 route hasn't been posted. On past tours, Hinkle has told stories tied to Murf's Backstreet Tavern, the Old Whalers' Church and the former home of Spalding Gray, as 27east has reported. This year's stops may differ. Either way, the tour stays within a few blocks of Main Street. It costs about the same as a dinner entrée and takes an hour, and it ends back at the museum's front door. The museum plays host again a week later.
October 24 and 25: The Book Before the Movies
The Frankenstein thread starts at the Whaling Museum on Saturday, October 24, at noon, with a community reading of part of Frankenstein; or, The Modern Prometheus. The Masonic Lodge, the Whaling Museum and Canio's Cultural Cafe are co-sponsoring it. Anyone who wants to read signs up in advance through the museum's online form. Copies of the novel are for sale through Canio's online bookshop.
The museum's announcement makes a simple point. Nearly everyone knows the monster from films, costumes, cookies and cocktails. Far fewer people have read the novel. Before the October screenings begin, the village gets an afternoon with the book itself, read by neighbors.
The films start the next day. On Sunday, October 25, at 12:30, the Masonic Lodge Auditorium runs a Frankenstein marathon. On the bill are the 1931 Frankenstein, Bride of Frankenstein from 1935, Mel Brooks's Young Frankenstein from 1974, "and more." It's the same 1931 James Whale film that Sag Harbor Cinema will screen six days later with a live score. Anyone who goes to both will see one film in two very different settings within a week, first in the Lodge auditorium and then in the Cinema.
October 25: The Parade Ends Where the Reading Began
That Sunday afternoon, the Main Street crowd heads back to the museum. The Ragamuffin Parade is the Sag Harbor Chamber of Commerce's open-invitation Halloween march. The Chamber's listing invites "children, adults and even pets." Marchers line up on Nassau Street near the laundromat and parade up Main Street to the Whaling Museum.
A carnival on the museum lawn is listed for 1:30 to 2:30 p.m. The Bridgehampton School Drama Club is hosting it, with games, activities and music. Published parade times don't quite match that window, so check the Chamber's page before you leave the house. The tradition goes back a long way. The East Hampton Star's "The Way It Was" column for October 30, 2025, looking back 25 years, records the parade as an annual event in 2000.
So in nine days the Whaling Museum hosts three different crowds: the walking tour on the 17th, the readers on the 24th and the parade on the 25th. Each event is run by different people. The museum's lawn and front steps hold the first half of the month together.
October 30 to November 1: Three Stages, One Party
The last weekend belongs to the village's three arts venues. The Third Annual Spooky-Palooza is a joint production of Sag Harbor Cinema, The Church and Bay Street Theater. The new event this year is the one that best shows how the weekend works. On Friday, October 30, from 6 to 9 p.m., The Church at 48 Madison Street hosts a Spooky-Palooza Dance Party and Costume Contest, with DJ Henry Eau, free food tables, a cash bar and a grand prize for best costume. Tickets are $90 each, or $75 per person for groups of two or more.
The party is held at The Church, and every ticket includes a free spooky spritzer at Sag Harbor Cinema's Green Room, before or after. All proceeds are split among The Church, Bay Street Theater and Sag Harbor Cinema. Harbor Market, Kidd Squid and Page are listed as community sponsors. One ticket supports three nonprofits and takes you to two of their buildings in a single evening.
On Sunday, November 1, The Church closes the weekend with a Fall Fun Creativity Lab from noon to 2 p.m. It's $15 per person and open to all ages.
October 31: The Day the Handoffs Get Tight
Halloween falls on a Saturday this year, and that sets the day's schedule. The Chamber runs its Pumpkin Trail on Main Street from 3 to 5 p.m. on weekdays and from 1:30 to 3:30 p.m. on weekends. This year trick-or-treating starts mid-afternoon, and the arts venues have built their schedules around it.
| Time | Event | Where | Ticket |
|---|---|---|---|
| 11 a.m. | Frankenweenie matinee, free popcorn | Sag Harbor Cinema | $18.50 adults, $13.50 children, $15.50 seniors, $10 members |
| 12:30 to 1:30 p.m. | S'mores and Scares, a staged reading of spooky stories | Bay Street Theater | $15 |
| 1:30 to 3:30 p.m. | Pumpkin Trail | Main Street businesses | Free |
| 6 p.m. | Frankenstein (1931), live guitar score by Gary Lucas | Sag Harbor Cinema | Through sagharborcinema.org, price not listed |
| 8 p.m. | The Rocky Horror Picture Show | Bay Street Theater | $25.99 for one, $40.99 for two |
Bay Street's S'mores and Scares ends just as the Pumpkin Trail begins, on purpose. After the campfire stories, children get the red-carpet treatment for costume photos with the young actors, receive a goody bag of Halloween and campfire treats, and are then sent off to trick-or-treat down the Pumpkin Trail. A Frankenweenie matinee repeats Sunday, November 1, at 11 a.m. for families who'd rather keep Saturday morning free.
The Pumpkin Trail is the oldest part of the day. The Chamber says it has run the trail for more than 40 years, and it calls Sag Harbor the first village to invite children to trick-or-treat at local businesses, an idea that later spread across the East End. The rule for kids is simple. Any child in costume can stop at a Chamber member business with a Pumpkin Trail sign in the window, and the Chamber promises "no tricks required!"
In the evening, the month's Frankenstein thread ends where it started, with the 1931 film. Sag Harbor Cinema screens James Whale's Frankenstein at 6 p.m. with a live solo-guitar score by Gary Lucas. The Cinema's page links to tickets but doesn't list a price. A week earlier, the same film played at the Masonic Lodge marathon. Here it comes with a live musician and closes out the Cinema's part of the weekend. Two hours later, The Rocky Horror Picture Show screens at Bay Street. The organizers say the weekend will "honor the late Tim Curry." Rocky Horror tickets are sold through Bay Street.
Booking Order, If You Want All of It
Some of these events are free and some need tickets, and the ticketed ones sell through four different box offices. A practical order:
- Register for the October 17 Haunted Walking Tour through the Whaling Museum.
- Sign up to read at the October 24 Frankenstein reading through the museum's form, if you'd like to read a passage yourself.
- Buy Friday dance party tickets from The Church. The group rate makes sense for any household of two or more.
- Get tickets for Frankenweenie and the Gary Lucas Frankenstein screening at sagharborcinema.org.
- Book S'mores and Scares and Rocky Horror through baystreet.org.
The parade and the Pumpkin Trail need no tickets, just a costume. Bay Street's ha ha hamptons comedy show, moved after the nor'easter, now plays October 11 at 8 p.m., the festival's second-to-last day. Once Halloween is over, Bay Street opens Aaron Sorkin's adaptation of To Kill a Mockingbird, directed by Stephen Hamilton, from November 9 to 29. The Whaling Museum's Annual Holiday Party follows on Saturday, December 5, from 5 to 7 p.m.
The Ragamuffin Parade lines up on Nassau Street, and the Pumpkin Trail runs from shop window to shop window along Main Street. In Sag Harbor, the houses within walking distance of both are some of the most personal addresses in the village. If you'd like to be walking to the Pumpkin Trail from your own front door next October, Jennifer Friedberg knows these blocks house by house. Schedule a private consultation.
