Edgartown, Vineyard Haven, and Oak Bluffs are doing a bang-up job helping folks of all ages celebrate the Halloween season.
Kick things off early with a holiday-themed craft, decorating a tote perfect for trick-or-treating at the Vineyard Haven library on Thursday, Oct. 24, from 3:30 pm to 5 pm. The next day, in Oak Bluffs, the Red Cat holds its second Halloween Drag Show. Doors open at 9:30 pm for an evening of drag, cabaret, dancing, spooky cocktails, and more. (Admission includes two drink tickets, a welcome Jell-O shot, goody bags, and costume contest entry.)
Oak Bluffs will also be hopping on Saturday, Oct. 26. There will be a kids’ costume parade and contest at Island Outfitters at 1:45 pm. From noon to 3 pm, you can get your pooch involved in the dog costume contest at the Canine Co., as well as decorate pumpkins at the Dockside Inn. At 3 pm, there is Trunk or Treat with the Oak Bluffs Elementary School at Washington Park. From 3 to 5 pm, Enchanted Chocolates will host an open house with tarot card readings. Also on Oct. 26, the Strand Theater has a lineup of spooky movies, starting with “Monsters, Inc.” at noon, “The Corpse Bride” at 3 pm, and “Rocky Horror Picture Show” at 7 pm. On the same day, Edgartown celebrates the Barnyard Boo from 10:30 to noon at the FARM Institute, and an Edgartown Yacht Club Halloween Cocktail Party from 6 to 8 pm.
Edgartown’s Happy Haunting will be held on Sunday, Oct. 27, from 10 am to 1 pm, featuring little ghosts and goblins trick-or-treating from business to business.
Vineyard Haven starts celebrating on Wednesday, Oct. 30, at M.V. Screenprinting, which transforms into a house of horror. From 4 to 5 pm, enjoy kid-friendly spooks for the whole family. From 6:30 to 11 pm, the lights go out, and only the bravest may enter. (Admission is $5 for kids and $7 for adults, with proceeds benefiting the Tisbury Fire Department.)
The town of Vineyard Haven also pulls out all the stops on Halloween itself, Oct. 31. From noon to 5 pm, there is Bark and Boo at the Chamber of Commerce, where you can swing by with your kids and pups for photo ops and treats. (A portion of proceeds will go to the M.V. Animal Shelter.) Stop in for the final holiday craft and a spooky movie at the Vineyard Haven library from 3:30 to 5 pm, as well as trick-or-treating and hot cider from 5 to 8 pm. The big Halloween Parade, trick-or-treating, and costume contest starts at the Mansion House at 4 pm, winding its way down Main Street, stopping at participating businesses and the homes along historic William Street.
M.V. Museum is also celebrating on Oct. 31 with a free Halloween on the Hill, from 4:30 to 6:30 pm, with a delightful evening of trick-or-treating, engaging arts and crafts, delicious snacks, lawn games, and a hands-on history children’s exhibit in the courtyard. And the final hurrah on Oct. 31 is an adults-only celebration with costumes, prizes, food, and drinks at Vineyard Haven’s S&S Kitchenette Halloween Party, from 8 to 10 pm.
So, put those last-minute touches on your costume and gather your trick-or-treat tote for a week of fun around the Island.