Guests ask us at the front desk what's happening around the island all fall. This guide covers the events that come back every year. Each one lists this year's dates alongside next year's. The 2027 dates are our best guess from past years, so check with the organizers before you go. For more, see the Chincoteague Chamber of Commerce events calendar.
October
Farmers & Artisans Market. The Cultural Alliance's Saturday market at the Community Center for the Arts on Church Street, with the Kitchen Gallery open at the same time.
2026: Saturdays through October 31, 9am to 1pm
2027 (tentative): Saturdays through October 30Assateague Lighthouse climbing. The lighthouse on the refuge opens for climbing on select fall Saturdays.
2026: Saturday, October 24, from 10am
2027 (tentative): TBARefuge fee-free day for Theodore Roosevelt's birthday. The U.S. Fish and Wildlife Service waives the refuge entrance fee.
2026: Tuesday, October 27
2027 (tentative): Wednesday, October 27Weaving and Wine. A beginner weaving class at the Cultural Alliance. Register ahead.
2026: Wednesday, October 28, 6:30 to 8:30pm
2027 (tentative): Not scheduledStory Swap. An open storytelling night at the Cultural Alliance on the last Friday of the month. Admission is free. October's theme is ghost stories.
2026: Friday, October 30. Doors open at 6:30, stories start at 7
2027 (tentative): Friday, October 29Halloween at the farmers market. Kids trick-or-treat at the vendor booths and decorate pumpkins, and there's a costume parade with prizes.
2026: Saturday, October 31, 9am to 1pm. Parade at 11
2027 (tentative): Saturday, October 30Trick or Treat Main Street. Shops along Main Street hand out candy, and the island library gives away free children's books.
2026: Saturday, October 31, in the evening
2027 (tentative): Sunday, October 31, in the evening
Walking or biking into the refuge is free every day; fee-free days cover the vehicle pass. Chincoteague National Wildlife Refuge
November
Fall dinner theatre. The Chincoteague Island Theatre Company stages a dinner theatre show at the Cultural Alliance. In 2026 it's Bad Apples. Tickets are sold online only.
2026: November 7, 8, 13 and 14
2027 (tentative): TBARefuge fee-free day for Veterans Day. The U.S. Fish and Wildlife Service waives the refuge entrance fee.
2026: Wednesday, November 11
2027 (tentative): Thursday, November 11Paint a Cardinal on Slate. A painting class with Cheryl Taylor at the Cultural Alliance.
2026: Sunday, November 15, 2 to 5pm
2027 (tentative): Not scheduledIsland Concert Stage. A fall concert at the Cultural Alliance. In 2026 it's Trio Niche playing classical music on violin, cello and pianoforte.
2026: Saturday, November 21. Doors open at 6:30. $15, or $5 under 18
2027 (tentative): TBAChristmas Craft Fair. A two-day craft fair at the Chincoteague Center on the weekend before Thanksgiving.
2026: Saturday and Sunday, November 21 and 22
2027 (tentative): Saturday and Sunday, November 20 and 21Waterfowl Weekend. The refuge opens the Wildlife Loop to cars from 9am to dusk over Thanksgiving weekend. On certain afternoons you can also drive the Service Road, which is closed to private vehicles the rest of the year.
2026: Thanksgiving weekend. Service Road drive Saturday and Sunday, November 28 and 29: enter through the Wildlife Loop between noon and 2pm and leave by 4
2027 (tentative): Thanksgiving weekend, November 25 to 28. Service Road days TBAHolly Day Market. The Cultural Alliance's holiday market on the Saturday after Thanksgiving, with free Kid Art on the porch for ages 2 to 10.
2026: Saturday, November 28, 9am to 1pm
2027 (tentative): Saturday, November 27Christmas tree lighting. The island lights its Christmas tree on the Saturday after Thanksgiving.
2026: Saturday, November 28
2027 (tentative): Saturday, November 27Small Business Saturday. Shop small downtown, and stop by the Rookery, our gift shop, for its annual Shop Small Saturday sale.
2026: Saturday, November 28
2027 (tentative): Saturday, November 27It's a Wonderful Life. The Island Theatre shows it on the Saturday after Thanksgiving.
2026: Saturday, November 28
2027 (tentative): Saturday, November 27
Our Thanksgiving weekend itinerary covers meals and the rest of the weekend.
December
Homes for the Holidays tour. A tour of island homes decorated for the season, on parade day.
2026: Saturday, December 5, 10am to 3pm. Tickets are available at Hollyhocks on Main St.
2027 (tentative): Saturday, December 4Old-Fashioned Christmas Parade. The parade comes down Main Street on the evening of the first Saturday in December.
2026: Saturday, December 5, 6pm. Theme: "A Star-Spangled Christmas," for America's 250th anniversary. Weather date Friday, December 11
2027 (tentative): Saturday, December 4, 6pmHoliday Cookie Sale. The Cultural Alliance sells a beautiful, impressive assortment of homemade holiday cookies. Bring your own boxes and simplify your holiday baking.
2026: Saturday, December 19, 11am to 1pm
2027 (tentative): TBA
The Chincoteague Chamber of Commerce puts on the parade. Parade details
Plan Your Stay
Most of these events land on a Saturday, and weekends here typically book up through the fall. If you can, add a night or two on either side. Weeknights are quieter here, the rates are lower, and you'll likely have the pool to yourself.
For 2026, our Two + Tuesday special runs through November 26: book three nights that include a Tuesday, and the Tuesday is half price. From November 29, our "Stay Two, Get One Free" winter special takes over. Christmas Parade weekend qualifies for that special!