Vineyard Haven's Halloween is a schedule. It starts at the Mansion House at 4 p.m. on Saturday, moves down Main Street past the businesses still open, and ends on William Street once the porch lights come on. Over about two hours the town goes from shopkeepers handing out candy to neighbors handing it out. The season does the same thing on a longer clock. Through October, summer storefronts have been closing for the year, and the people who stay are taking over what is left.
This year Halloween lands on a Saturday, so the haunted house on State Road runs Friday and Saturday nights and the parade has a full weekend afternoon. Here is how the weekend fits together.
Friday and Saturday on State Road
The weekend starts outside downtown. Martha's Vineyard Screenprinting has turned its headquarters at 426 State Road into a haunted house every year since 2019, with the money going to the Tisbury Fire Department. The MV Times Tisbury column lists it for Oct. 30 and 31 this year, with an early session for kids with the lights on and a scarier one later in the evening.
The shop hasn't posted this year's hours and prices yet. Last year the Vineyard Gazette reported kid-friendly frights from 4 to 5:30 p.m. and adult hours from 5 to 10 p.m. Admission was $5 for children 10 and under and $10 for adults. That same year the MV Times listing gave different session times, so check the shop's events page before you go. The events page is also looking for volunteers this year, and they must be 18 or older.
Organizer Chris Maciel told the Gazette last fall what he enjoys most about it.
"Our favorite part is having everyone running and screaming out of here. It's so rewarding to hear people get scared. They're either laughing, screaming or crying."
If last year's hours hold, the kids' session overlaps with Saturday's parade. That makes Friday the easier night for families who want to do both.
4 p.m. at the Mansion House
The Vineyard Gazette's calendar listing says it was created in 2010 by Bella, Bob Lee and Carol Loud, and its star is a monkey puppet named Arakataka. Anyone can join, in costume or not. The organizers invite people to bring a favorite puppet or make one, and the listing says the parade is "weather permitting." In this year's Tisbury column, Bella leads the march down Main Street with "her larger-than-life handmade puppets."
The column gives a 4 p.m. start at the Mansion House. The MV Times event listing puts it somewhere between 3:45 and 4:15 p.m. and says final times still need to be confirmed locally. Getting to the Mansion House a little before 4 covers both.
The handoff, hour by hour
The rest of Saturday runs in a set order. Times without a 2026 source come from last year's pattern.
| Time | Where | What happens |
|---|---|---|
| About 4 p.m. | Mansion House, Main Street | The puppet parade lines up and starts down Main Street |
| After the parade | Downtown businesses, then 35 Main St. | Trick-or-treating at shops that are open, then Visit Vineyard Haven's TisScary Halloween Happenings with music and a costume contest |
| 4:30 to 6 p.m. | M.V. Museum, 151 Lagoon Pond Road | Halloween on the Hill, with treats, crafts and games |
| 5:30 p.m. in 2025 | William Street | Trick-or-treating at homes, with parts of Spring and William streets closed to cars until about 9 p.m. last year |
The first hour depends on the storefronts. The MV Times listing describes trick-or-treating "at participating local downtown businesses." TisScary picks up after the parade at 35 Main St. The costume contest has moved around over the years. In 2024, Visit Vineyard Haven held it at Linden Tree Park next to the Capawock Theater, before 5:30 p.m.
Elaine Barse, president of the Vineyard Haven Business Association board, told the Vineyard Gazette last year that the costumes are what she always points out.
"People make them so much fun. It makes it a nice little Fall thing to look forward to."
Once it gets dark, the crowd moves to William Street, which the Gazette calls "the place to be for trick or treating on Halloween." Last year it got going at 5:30 p.m. If the same parts of Spring and William streets close to cars until about 9 p.m. this year, plan to park farther out or walk in.
For young children or anyone who wants something quieter, Halloween on the Hill at the Martha's Vineyard Museum runs from 4:30 to 6 p.m. at 151 Lagoon Pond Road. It has candy and non-candy treats, seasonal crafts, popcorn, games and a quiet sensory space. Admission is free, and donations are welcome.
Which storefronts are still open
The shop hour of the parade only works where a business has its lights on, and by late October fewer of them do. The MV Times Tisbury column listed Fish MV, Grace Church's Friday lobster rolls and Lani Beach Club as closed for the season in mid-September. On Oct. 21 the column added El Barco.
One of those closed spaces has other tenants for the holidays. Martha's Vineyard Made is running a pop-up inside Lani Beach Club with 14 local artists, according to the Oct. 14 Tisbury column. It's open Friday through Sunday in October, with longer hours starting after Thanksgiving, and it stays through New Year's Eve. The space sits between Nochi and Bunch of Grapes, and Lani plans to reopen as usual in spring 2027. Halloween falls on a Saturday this year, so the pop-up should be open on parade day.
A few other events in town this week:
- Thursday, Oct. 29. S&S Kitchenette hosts another "Esoteric Evening" from 4 to 8 p.m., with drinks, bites and tarot.
- Through Nov. 15. The Workshop Gallery's group show "The Museum of Unnatural History" stays up into November.
- Any afternoon this week. The Tisbury columnist recommends leaf-peeping walks along William Street and West Spring Street. For a longer walk, try Oak Grove Cemetery, which the column says has "truly blazing colors."
The off-season gets to work
After the costumes, the town's attention goes to the jobs that are easier with the harbor empty. On Oct. 23, the MV Times reported that the Tisbury Harbor Department had finished a $66,000 extension of the Lake Street dinghy docks to ease summer crowding. Martha's Vineyard Shipyard delivered three new sections of dock float to Lake Street Landing. John Packer of R.M. Packer Co. used his barge to drive in three pilings that were reused from the Owen Park Pier reconstruction.
Lake Tashmoo has more than 350 moorings, many of them in the Lake Street mooring field. Boaters there depend on the dinghy dock and beach strip to store their dinghies. Tashmoo boaters Lynne Fraker and Paul Munafo and mooring installer Ray Gale proposed the project in 2023. It took four years and three harbormasters to finish: John Crocker, Gary Kovack and now Michael Gately. Crocker put it this way in the harbor department's release.
"This project took several years to complete, but it's an example of what can be accomplished when the whole boating community works together."
Gately said it was the second long-planned pier project the town has finished in 2026, after Owen Park Pier. Next summer, Tashmoo boaters coming ashore at Lake Street will have room for more dinghies.
Neighbors are also helping neighbors through the winter. MV Connect, a program of Healthy Aging M.V., is looking for volunteer drivers for the off-season to take people without other transportation to their appointments. The Oct. 14 Tisbury column says to call Diane at 508-560-4514 to get started.
Our team at Donnelly + Co. works on the island year-round, and the months after Halloween are when we have time for slower conversations. If you're thinking about what a Vineyard Haven winter would mean for your home, whether that's a rental after the summer ends or a question about next spring, contact us. We're happy to talk it through over coffee on Main Street.
