Sag Harbor's Halloween season comes down to two afternoons. The village's annual Ragamuffin Parade steps off on Sunday, October 25 at 1 p.m., and the Pumpkin Trail sends costumed children trick-or-treating through the business district on Saturday, October 31, from 1:30 to 3:30 p.m.

Both are Sag Harbor Chamber of Commerce traditions, and both run in daylight in the walkable center of the village.

Nassau Street to the Whaling Museum

Parade participants line up on Nassau Street, near the laundromat, and march along Main Street to the Sag Harbor Whaling and Historical Museum. The parade is open to everyone: children, adults and pets, with costumes encouraged for all three.

The finish line doubles as a party. The Whaling Museum hosts its Ragamuffin Parade Carnival on the museum grounds from 1:30 to 2:30 p.m., picking up as marchers arrive off Main Street.

A museum weekend on either side

The carnival caps a Halloween stretch at the museum. On Friday, October 23 at 5:30 p.m., the museum runs a haunted walking tour through the village, with registration required through its events page. On Saturday, October 24 from noon to 4 p.m., it hosts a community reading of a portion of Frankenstein, Mary Shelley's novel, open to listeners and readers.

The Pumpkin Trail on Halloween

On Halloween itself, the chamber's Pumpkin Trail takes over the shopping streets. From 1:30 to 3:30 p.m., children in costume trick-or-treat at participating chamber member stores, identified by Sag Harbor Pumpkin Trail signs in their windows. The format keeps the afternoon simple: find a sign, collect a treat, move down Main Street to the next one.

The two events land one week apart: the parade and carnival on the 25th, the trail on the 31st.

If you go

The Ragamuffin Parade lines up on Nassau Street on Sunday, October 25 at 1 p.m. and ends at the Whaling Museum on Main Street, where the carnival runs 1:30 to 2:30 p.m. The Pumpkin Trail runs Saturday, October 31 from 1:30 to 3:30 p.m. at participating stores displaying the trail sign. Registration for the haunted walking tour is on the Whaling Museum's events page.

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