Carved pumpkins and stocked candy bowls can only mean one thing — let Halloweekend on the Island begin! There are plenty of options, and our one and only tip: Let’s all be adults and have a costume or two ready.
Friday, Oct. 28
Discover “creatures of the night” at Felix Neck from 5 to 7 pm on Friday night, with a host of activities that promise not to frighten. Kick off with a hayride at 5:15 pm, take a self-guided night walk, create animal masks, roast marshmallows by the fire, and take a walk through the “Trunk or Treat” hosted by the Oak Bluffs PTO. Admission is $15 per car for members, and $20 per car for nonmembers.
Saturday, Oct. 29
All weekend until Halloween, the Great Pumpkin Hunt will be on in Vineyard Haven. Find the hidden purple pumpkins at over 30 participating stores around Vineyard Haven and get entered into the grand prize drawing at 4:30 on Monday, Oct. 31, at Bunch of Grapes.
The Oak Bluffs library is hosting a Halloween party for kids of all ages from 10 to 11:30 am. Arrive in costume, walk through the haunted tunnel, enjoy festive snacks, and get in on the spooky games.
The haunting continues in downtown Edgartown for their annual Halloween celebration from 11 am until 3 pm. Get ready for costume contests, dance parties, and of course, all the candy imaginable.
If you’re up-Island check out the Halloween Party at the Aquinnah library, starting at 1 pm. More tricks, treats, and opportunities to have that costume recognized.
At 4 o’clock, make your way over to Circuit Avenue in Oak Bluffs for everybody’s favorite Halloween tradition: trick-or-treating. Kids, adults, and pets, put on your costumes and meet at the information booth next to the Flying Horses. Parade up the street and keep an eye out for stores with pumpkins in the window— those are the candy jackpots. There will also be a haunted house out front of Linda Jean’s between 4 and 6 pm.
The after-dark festivities begin at 5 pm at the FARM Institute, where the Yard will host a “Haunted Barn.” Join for ghost stories and hayrides through the fields. Walk through the farm to see “Silo,” a new dance piece by the Yard with artist educators Leah Crosby and Danielle Doell. Cider around the fire will be available.
Pay homage to the French Carnivale days of old, with a twist of voodoo at The Barn Bowl and Bistro’s Bizarre Carnivale from 8 pm until midnight. There will be prizes for the freakiest ensemble, and music by DJ Di and guests. The event is 21+ and tickets are $20 advance, $25 at the door.
Sunday, Oct. 30
Bring your carved pumpkin to Main Street, Vineyard Haven anytime between 12 and 4 pm for a chance to win this year’s pumpkin carving contest. The judging begins at 5 pm, and cash prizes will be awarded to the spookiest, funniest and most original pumpkins. Participants are encouraged to leave their pumpkins on display in town.
Monday, Oct. 31
If by Monday you still haven’t had enough, a day-of Halloween party begins at 3:30 pm at the West Tisbury library. Come in costume, hop on a hayride, make crafts, and munch on some spooky snacks.
Join friends in Vineyard Haven for a haunted Halloween trick-or-treat celebration at the Tisbury Town Hall. Come before or after the Main Street parade from 3:30 to 5:30 pm.
The Vineyard Haven Main Street costume parade begins at 4 pm.
Kids in third grade and up looking to get scared by a good old fashioned ghost story can head to the Edgartown Public Library from 3:35 to 4:45 pm.
The Vineyard Haven Public Library will also hold special evening hours on Halloween. They’ll be open until 8 pm for a break from trick-or-treating, to enjoy cider and candy with friends at the library.
The West Tisbury Parks and Recreation department will host a party from 6-8 pm at the Ag Hall. There will be games, prizes, refreshments, and a spooky hayride.
The P.A. Club wraps up the Island-wide celebrations at 8 pm with its annual Halloween celebration, complete with live music by Serendipity.
A reminder to Oak Bluffs residents that Vineyard Avenue will be closed on Halloween.
We hope everyone has fun, stays safe, and does it big for the spookiest weekend of the year.
