Nantucket Fall Events & Calendar 2026
Fall is one of our favorite times of year on Nantucket. The summer crowds thin out, but the island doesn't simply shut down. October brings scalloping, art, cranberry season and Halloween, while November transitions into some of Nantucket's best-loved holiday traditions.
If you're planning a fall visit, here are the dates we'd put on the calendar.
October 2026 — Cranberries, Art & Halloween
October 9–11 — Wet Paint Weekend. The Artists Association of Nantucket's fall art weekend is one of the island's annual October traditions. It's a wonderful weekend to explore Nantucket's art scene while enjoying the quieter side of the island. Events -
October 16 & 21 — Cranberry Harvest Walks. The Nantucket Conservation Foundation is hosting guided walks through historic Milestone Cranberry Bog from 8:30–10:30 a.m. Visitors can see the harvest and learn about Nantucket's cranberry-growing history. Nantucket Conservation Fund
October 25 — Fall Festival & Batacular Bike Race. One of our favorite family events of the season takes place at Milestone Cranberry Bog from 10 a.m.–2 p.m. Expect hayrides, children's games, live music, food trucks and Nantucket cranberries. The accompanying bike race travels through the Middle Moors, with 8.4- and 16.8-mile options. Nantucket Conservation Foundation
October 28 — Trails & Treats. The Linda Loring Nature Foundation hosts an afternoon of Halloween- and nature-themed activities along its trails from 3–5 p.m. Events -
October 30–31 — Halloween Weekend. Halloween is surprisingly fun on Nantucket. The Whaling Museum hosts a spooky walk-through and trick-or-treating on October 30. On Halloween itself, downtown comes alive with the annual Halloween Parade at 3:15 p.m., followed by Halloween in the Courtyard at the Nantucket Atheneum and other activities. Nantucket Dreamland is also showing free Halloween movies throughout the day. Events -
November 2026 — Nantucket Noel Begins
Beginning November 1, the island transitions into Nantucket Noel, the Chamber of Commerce's holiday season celebration that runs through December 31.
Downtown gradually fills with Christmas trees and decorations, shops prepare for the holidays, and the Chamber's Red Ticket shopping program begins November 1. Nantucket Island Chamber of Commerce
November 23 — Festival of Wreaths Preview Party. The Nantucket Historical Association kicks off one of the island's prettiest holiday traditions with its preview party at the Whaling Museum from 5–7 p.m. Events -
November 24–28 — Festival of Wreaths. The Whaling Museum fills with imaginative wreaths created by island residents, businesses, schools and organizations. It's a great event to catch if you're spending Thanksgiving week on Nantucket. Nantucket Island Chamber of Commerce
November 26 — Thanksgiving on Nantucket & Turkey Plunge. Thanksgiving morning brings the Nantucket Atheneum's annual Cold Turkey Plunge—2026 marks its 25th year—with participants braving the water to support the Weezie Library for Children. Around Town, restaurants, shops and holiday activities make Thanksgiving weekend the unofficial beginning of the Christmas season. Nantucket Island Chamber of Commerce
November 27 — Tree Lighting & Community Caroling. This is one of the events we'd especially recommend. At 4 p.m. on the day after Thanksgiving, more than 150 Christmas trees illuminate downtown Nantucket while the community gathers for music and caroling. Main Street is closed from noon until 6 p.m. Nantucket Island Chamber of Commerce
And Don't Miss Christmas Stroll
Technically it's December, but no Nantucket fall calendar would feel complete without mentioning it.
December 4–6 — 52nd Nantucket Christmas Stroll
For more than five decades, Christmas Stroll has been one of Nantucket's signature weekends.
Santa arrives by Coast Guard vessel at noon Saturday before making his way up Main Street by fire truck. Downtown fills with Victorian carolers, holiday entertainment, decorated storefronts, crafts and the Christmas Stroll Marketplace. The Marketplace runs Saturday, December 5, from 10 a.m.–3 p.m. Nantucket Island Chamber of Commerce
Robert & Daryl's Fall Favorites
If we had friends coming to Nantucket for only one fall weekend, we'd probably choose October 23–25 for the quieter fall experience and the Fall Festival, or Thanksgiving weekend for the transition into the holidays.
October is Nantucket at its most relaxed—cranberries, scalloping, long beach walks and cooler days. Thanksgiving weekend is completely different: Town begins to glow for Christmas and you get a preview of the atmosphere that makes Christmas Stroll so special.
That's part of what we love about living here. Nantucket doesn't stop being Nantucket when summer ends. In many ways, that's when you get to know the island best.
For day-by-day listings, the Nantucket Events Calendar is worth bookmarking, as events and schedules continue to be added.
Robert & Daryl Westbrook
Westbrook Real Estate, Siasconset, Nantucket, Massachusetts
Nantucket is our home. Real estate is our family business.
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