Did you know that Martha's Vineyard is full of Halloween activities? And not just for the little ghosts and goblins. With Halloween on a Friday night, we have a full week of frightfully good fun for you to enjoy! We've got your go to guide (with a couple fun Fall finds as well) - A Hauntingly Good Time: Halloween on Martha's Vineyard.
Let's start with the weekend before Halloween. Get ready for Edgartown Haunting, Halloween in Oak Bluffs, a zombie crawl, spooky mysteries and more!
Saturday, October, 25th
Halloween in Oak Bluffs - All Treats, No Tricks for Kids of Every Age!
Trick or Treating: Visit downtown businesses for Halloween treats, 1pm - 4pm. Keep an eye out for spooky shop owners!
Flying Horses Halloween Party: Enjoy the magic of the country's oldest carousel. Costume party contest at 2:30pm, free popcorn, 1pm - 4pm.
Halloween Costume Parade: From Washington Park to the Flying Horses Carousel, line up at 2pm.
Trunk or Treat: Head to Washington Park for pumpkin decorating, horse drawn carriage rides, face painting, trick or treating and more! A fundraiser for the Oak Bluffs School, 3pm - 5pm
5th Annual Harvest Festival - The Ag Hall
Enjoy all the classics - pumpkin carving, farm animals, hay maze, crafts for kids, demos for adults, local bites (Reunion Pizza, Full Moon Food Co, Little Rock Farm, You Enjoy My Vegan) a pie eating contest, live music, a Halloween Costume Swap and more, 10am - 2pm. Click here for a complete list of events.
Harvest Style Pop-Up at the PA Club - Fall Finds From Local Artists
Enjoy local artists and food from Mo's Vendors include Sugar and Stone Chocolates, Relovdecor, Gilly B, Sara Barrington, Ivry Belle Jewelry and more. Be sure to come hungry. Mo's will have some tasty specials and desserts, 11am - 3pm. Picture courtesy of Sugar and Stone Chocolates.
Ponies & Pumpkins
Bring the whole family for a festive fall morning at Misty Meadows! Enjoy pumpkin decorating, kids’ games, face painting, delicious baked goods, cider, and, of course, the Misty Meadows ponies. It’s a perfect way to celebrate the season with fun, food, and furry friends for all ages, 10am - 12pm. Picture courtesy of Misty Meadows
Sunday, October 26th
Edgartown's Happy Haunting - The town’s historic downtown transforms into a picture-perfect Halloween scene
The Halloween festivities continue in Edgartown, where little ghosts, goblins, and ghouls can make their way from shop to shop collecting treats and enjoying the festive downtown spirit. Businesses throughout historic Edgartown open their doors for safe, family-friendly trick-or-treating — and the fun goes on rain or shine! So bundle up and get ready for a hauntingly good time by the harbor, beginning at 10am. Be sure to grab lunch at the Wharf, Rockfish, Town MV or Bad Martha Farmer's Brewery where you will find ghoulishly good Fall food and drinks.
Tuesday, October 28th
Spirits at Spirits at Hotel Le Grange
This Halloween season, enter a place out of time at The Grange Hall in West Tisbury . Step inside Hotel Le Grangé, a faded seaside hotel steeped in a century-old atmosphere. The evening begins in the grand main hall, where music, libations, sweet indulgences, and curious company await. As night deepens, guests ascend to the top floor, where Island actors summon restless spirits through a haunting ghost story — one that lingers long after the final whisper fades.
The hotel lobby and bar open 45 minutes before the ticketed performance, inviting guests to arrive early, savor a drink, and soak in the eerie elegance of the setting. Come early, stay late, and lose yourself in the magic of Hotel Le Grangé. October 28th - October 31st, at The Grange Hall. Get your terrifying tickets here.
Wednesday, October 29th
The Witching Paddle Hour
This annual event is truly a special MV Halloween experience. Join Island Spirit Kayak and a cast of witches at the Oak Bluffs Harbor Launch on East Chop Drive. Bring your own paddle board or kayak and hat, cape and get ready to paddle around OB Harbor together. This is quite the sight - all sorts of witches paddling in the water laughing and cackling. The event is from 5pm to 6pm, weather dependent. Pictures courtesy of Island Spirit Kayak. To learn more, visit Island Spirit Kayak.
Thursday, October 30th
A Most Cold Bloody Butchery at the Martha's Vineyard Museum
Revisit one of Martha’s Vineyard’s most chilling mysteries — the unsolved axe murder of grocer William Cook Luce, slain at his downtown Holmes Hole (now Vineyard Haven) store on the night before Christmas Eve, 1863.
Join the MVM Chris Baer leads a captivating investigation into the century-old crime. Together, we’ll revisit the evidence, explore the three leading theories about the killer’s identity, and uncover what this haunting case reveals about the darker side of island life in the 1860s, 5pm at the Museum. Get your tickets here.
Annual Halloween Zombie Crawl
Zombie Up (or any costume!) and meet at Healey/Post Office Square and from there this spooktacular crowd will moan, grumble, snarl, hiss, growl, and grunt our way through the bars of Oak Bluffs — spreading spooky cheer (and maybe a little fear) all night long. Enjoy music at The Ritz, pumpkin beer and fun drinks at restaurants and more. The Fun starts at 7pm. Picture courtesy of AnicaBanica Photography.
Haunted House - MV Screenprinting Co.
Haunted House, an annual, community-driven Halloween tradition on Martha’s Vineyard — transforming a MV "Scream"printing into a terrifying haunted experience filled with scare actors, eerie effects, and spine-tingling surprises. The night begins with Kid-Friendly Spooks, perfect for families and younger visitors, before the lights go out for the truly brave during Lights Out Horror. Best of all, every scream supports a good cause, with proceeds benefiting the Tisbury Fire Department. Thursday, October 30th & Friday, October 31st. Kid Friendly, 4pm - 5:30pm, Lights-Out Horror, 7pm - 10pm. $10 per adult, $5 per child (10 and under).
HALLOWEEN
Howl-A-Ween Bark & Boo Bash
Paws up for one of the cutest Halloween traditions— the Howl-a-Ween Bark & Boo Bash at the MV Chamber of Commerce in Vineyard Haven! This spook-tacular celebration welcomes kids, families, and furry friends for an afternoon of festive fun. Pups can strut their stuff in the Costume Contest, pose for professional photos with Marilyn Roos Photography at the Pet Photo Stop & Repeat, and enjoy treats at the Trick-or-Treat Stations — with goodies for both dogs and their humans. Even better, a portion of the proceeds benefits the Martha’s Vineyard Animal Shelter, so every wag and woof supports a great cause, 12pm - 5pm at the Chamber. Featured here is Leah Fraumeni's new adorable pup,
Vineyard Haven Halloween
Trick or Treating in Vineyard Haven
After school, Main Street in Vineyard Haven comes alive with the sights and sounds of Halloween! Kids (and kids at heart) are invited to don their best costumes, grab their friends, and head downtown for trick-or-treating at local businesses. Don’t forget to stop by the DJ and costume contest next to the Capawock Theater, keeping the fun going with music, dancing, and prizes until 5:30 PM. It’s a classic Vineyard Halloween tradition — festive, family-friendly, and full of sweet treats. VHN Halloween parade picture courtesy of AnicaBanica Photography.
Vineyard Haven Puppet Parade
The Vineyard Haven Halloween Puppet Parade has been bringing smiles and spooky cheer to Main Street since 2010. Created by Bella, Bob Lee, and Carol Loud — and starring the mischievous monkey puppet Arakataka — this annual event invites everyone to join the fun. Gather in front of the Mansion House at 4 PM, where puppets big and small come to life in a colorful Halloween procession. Whether you arrive in costume or simply bring your favorite puppet (or one you’ve made yourself!), all are welcome to celebrate this playful and creative Vineyard Halloween tradition.
Halloween on the Hill
Families can enjoy a night of festive fun at the Halloween at the Museum celebration! Trick-or-treat through the exhibits with both candy and non-candy options, play games, make seasonal crafts, and snack on popcorn as you explore. A quiet sensory space ensures that every child can enjoy the festivities comfortably. Bring your candy bucket, come in costume, and experience Halloween magic throughout the Museum. All ages are welcome, 4:30pm - 6pm.
Trick or Treating
Islanders know just where to go for the best trick-or-treating on Halloween night. Favorite spots include Vineyard Avenue in Oak Bluffs — where the street is closed to traffic for safe, family-friendly fun — and William Street in Vineyard Haven, along with neighborhoods all across the Island. Wherever you choose to celebrate Halloween, we hope it’s a ghoulishly good time filled with treats, laughter, and community spirit. I live on Vineyard Avenue myself, and it’s one of my favorite nights of the year, I love Halloween — so if you’re out and about, stop by and say hi!
The Ritz Halloween Costume Contest
Get ready for a night of spooky fun and non-stop entertainment at The Ritz Halloween Costume Contest & Late Night Party! Come dressed in your most creative costumes and compete for $500 in prizes while enjoying live music from Agreeable Men. After the contest, the party continues with DJ Skrt spinning late-night tracks to keep everyone dancing. Whether you’re there for the costumes, the music, or just a fun Halloween vibe, this is one event you won’t want to miss.
Habitat for Humanity Dance Party
Get ready to dance the night away for a great cause at the Habitat for Humanity Dance Party! Join us at the PA Club for an evening filled with live music from Serendipity, a silent auction, and fun contests with prizes for the best mask, make-up, and costumes. Doors open at 7 PM — bring your friends, show off your creativity, and help support a wonderful cause while enjoying a night of music, dancing, and community spirit.
Saturday, November 1st
The Best Parade
Get ready — the Up-Is Land Band, Martha’s Vineyard’s very own second line parade band, is back and bringing their infectious energy to Oak Bluffs! Joined by special guest performers, they’ll fill the streets with music, rhythm, and a whole lot of Halloween spirit. Slip into your favorite costume and join the fun — expect dancing in the streets, spontaneous parades, and a bit of good old-fashioned shenanigans as the island celebrates Halloween, New Orleans–style! The event starts at The Strand Theatre, 7pm - 8pm.
Can you believe how many Halloween events are happening on Martha’s Vineyard? It truly is a Halloween wonderland — from parades and puppet shows to haunted houses and costume contests, there’s something for every ghost, goblin, and ghoul.
While Halloweening all around the Island, don't forget to check out all the Martha's Vineyard Charter School Scarecrows. Each year, families and students create scarecrows based on literary characters. Businesses sponsor the scarecrows which are on display throughout the towns October 25th - November 5th (at the latest). Come check out Point B's! This is one of our favorite Halloween traditions on the Island.
Did we miss an event? Email guinevere@pointbrealty.com and we’ll happily add it! After all, the more Halloween happenings, the better.