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A wet lane under the trees in fall, yellow leaves still on the branches and plenty more on the ground. The island’s color peaks in the Halloween week, two or three weeks after the mainland’s.
Halloween on Martha's Vineyard 2026, town by town: Edgartown's Happy Haunting on Sunday, October 25, Halloween in Oak Bluffs on Saturday, October 31, the museum's Halloween on the Hill, the library events, haunted Edgartown walks and Circuit Arts' revue at the Grange, plus how the Vineyard Haven puppet parade ran in past years (2026 date not announced yet).
Halloween on Martha’s Vineyard is a small-town holiday that runs for a week. In 2026 Halloween falls on a Saturday, and the Oak Bluffs Association has set Halloween in OB for the day itself, Saturday, October 31. Also posted for the 31st: Halloween on the Hill at the Martha’s Vineyard Museum, the West Tisbury library’s party, and evening hours with cider and candy at the Vineyard Haven library. In the days before come the Vineyard Preservation Trust’s haunted walking tour in Edgartown (October 22) and Circuit Arts’ Halloween revue at the Grange Hall (October 27 to 31). Also confirmed now: Edgartown’s Happy Haunting on Sunday, October 25. Vineyard Haven’s puppet parade is set for Saturday, October 31 at 4 PM, by the organizers’ save-the-date flyer. Martha’s Vineyard Screenprinting has now posted its haunted house for October 30 and 31. Not announced for 2026 yet: William Street trick-or-treating and the Ag Hall and Chilmark fire department parties. Confirmed events below carry their 2026 date; the rest are described as they ran in 2024 or 2025, with the year named.
The Strand Theatre on Oak Bluffs Avenue, which has shown spooky films during Halloween in OB in past years. Circuit Avenue, where the shop-to-shop trick-or-treating has been, starts around the corner.
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Confirmed for 2026: the Vineyard Preservation Trust’s Haunted Historic Edgartown Walking Tour with Seamus Rattigan, Thursday, October 22, 7 to 8:30 PM from the Carnegie on North Water Street, $30 a person, a benefit for the Trust. His regular Haunted Edgartown walk (90 minutes, $30, PG-13) runs Saturdays through October 31, usually at 7:30 PM, with 5:30 PM twilight walks on October 10, 17 and 31 for families who want to be home before dark. Confirmed for 2026: Happy Haunting, the Board of Trade’s shop-to-shop trick-or-treating downtown, on Sunday, October 25, 10 AM to 1 PM, rain or shine.
Confirmed for 2026: the Vineyard Haven Public Library at 200 Main Street stays open 5 to 8 PM on Saturday the 31st, with cider and candy from the Friends of the Library for families taking a break from trick-or-treating. The puppet parade is set for 4 PM on the 31st, by the organizers’ save-the-date flyer. Confirmed for 2026: the haunted house at Martha’s Vineyard Screenprinting, 426 State Road, on Friday and Saturday, October 30 and 31, with kid-friendly spooks from 4 to 5:30 PM and lights-out horror from 7 to 10 PM, $10 for adults and $5 for children 10 and under, the proceeds going to the Tisbury Fire Department. William Street isn’t announced for 2026 yet. In 2025 the parade left the Mansion House at 4 PM, William Street got going at 5:30 with parts of Spring and William Streets closed until about 9. The Chamber of Commerce’s Bark and Boo for kids and dogs ran noon to 5 PM at its Beach Street office on Halloween 2025.
Confirmed for 2026: Halloween on the Hill at the Martha’s Vineyard Museum, 151 Lagoon Pond Road in Vineyard Haven, Saturday, October 31, 4:30 to 6 PM, free with donations welcome: trick-or-treating, popcorn, games, seasonal crafts and a quiet sensory space, with costumes and candy buckets encouraged. For grown-ups, the museum’s talk on Thursday, October 29 (5 to 6 PM, registration on its events page) is Tales from the Grave, island historian Chris Baer on the Vineyard’s lost and unmarked burial places. Parking up the hill was very limited in 2025, so walking or biking up is the easy way.
Confirmed for 2026: Halloween in Oak Bluffs on Saturday, October 31, set by the Oak Bluffs Association and on the town calendar; the hours and program are not posted yet. In 2024, when it was held the Saturday before Halloween, it ran trick-or-treating at participating businesses from noon to 3, a costume parade from the Island Theatre at 2 with the contest winners named in Healy Square, movies at the Strand, a dog costume contest and mini-pumpkin decorating, and the Best Fest Parade with the Upis Land Band filled Circuit Avenue that evening. In 2025 Vineyard Avenue was closed to cars from 4 to 8 PM on Halloween night for the door-to-door crowd, and the Ritz threw a costume party with $500 in prizes. For grown-ups on the 31st, confirmed for 2026: a costume dance party for Habitat for Humanity at the Portuguese-American Club, 137 Vineyard Avenue, from 7 to 10 PM, with music by Serendipity, prizes for the best mask, makeup and costume, a silent auction and a raffle for two nights at the Charles Hotel in Boston. There is a suggested donation and a cash bar.
Confirmed for 2026: the West Tisbury library’s Halloween party on Saturday the 31st, 2 to 4 PM, free, with costumes, a hayride, games, spooky refreshments and trick-or-treating at the Field Gallery; How To Be A Witch, a read-aloud with potion making for ages 4 and up, at the same library on Thursday the 29th, 3:30 to 4:30; and Circuit Arts’ Halloween show, Spirits and Spirits: Vivienne Vale’s Vaudeville Revue, at the Grange Hall from October 27 to 31, $25 general admission, at 7:30 PM Tuesday to Friday and twice on Halloween itself, at 6 and 8:30 PM. Earlier, on Saturday, October 17 from noon to 1:30, the island libraries’ costume swap at the West Tisbury library lets families take home a gently used costume, with or without one to trade in. Not announced for 2026 yet: the Ag Hall party (in 2025 from 6 PM, with pizza, games and hayrides through the cemetery after dark) and the Chilmark Fire Department’s party at the Chilmark Community Center (5 to 5:45 PM on Halloween night in 2025).
Main Street in Edgartown under the trees, flags out and the shops open. On Sunday, October 25 these sidewalks fill with costumes from ten in the morning, the shopkeepers handing out the candy.
Halloween decorations on the shelves of the Chicken Alley Thrift Shop in October: skull candles, a skeleton paper lantern, a grim reaper candy bowl and garlands of fall leaves.
The week falls in the off-season, so the ferry has room, rooms are 40 to 60 percent below August, and the leaves are in full color. The Steamship Authority is on its fall timetable through October 22 and its winter one from the 23rd, so every boat lands at Vineyard Haven, roughly every 75 minutes, and a car is a flat $127 each way in October and $79 from November 1; a walk-on ticket is $11, and the fare-free bus reaches Vineyard Haven, Oak Bluffs and Edgartown. Vineyard Haven’s Main Street and library are a few blocks from the terminal, the museum is up the hill on Lagoon Pond Road, Oak Bluffs is a bus ride or a bike path away, and Edgartown is a bus ride too. Our ferry guide has the timetable, the fall guide the closures, and this weekend on the island will carry the confirmed times as the towns post them.
Edgartown Town Hall on Main Street in November, the garlands already up. Within days of Halloween the pumpkins come down and the holiday lights go up.
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The towns tend to post their Halloween programs in mid-October. Oak Bluffs held its celebration on the Saturday before Halloween in 2024 and 2025; for 2026 the association has picked Saturday, October 31 itself. The town, library and organizer pages, and this one, carry the final times in the last two weeks of October.
In 2025 Vineyard Haven closed parts of Spring and William Streets in the evening until about 9 PM, and Oak Bluffs closed Vineyard Avenue from 4 to 8; the 2026 closures are not posted yet. If you are staying on either street, parking before four has been the easy move.
Sunset is about 5:40 in the last week of October, and the door-to-door hours are after dark, on side streets. Reflective tape and a flashlight are the island parents’ rule.
The Chamber of Commerce’s Bark and Boo in Vineyard Haven has been the dog event (the 2026 date is not posted yet), and Halloween in OB has had a dog costume contest; the parades and trick-or-treat streets are crowded and loud, and plenty of families leave the dog at the house.
The clocks change on November 1 and sunset drops to 4:40. If Halloween is the trip, the Sunday is worth adding: the island is quiet and cheaper, and the October guide and the Christmas in Edgartown guide cover what comes before and after.
Step 1 · WhenMonth PickerTwelve months compared on NOAA numbers, crowds, prices and what is open. 
Step 2 · DaysDay-by-Day Trip PlannerMorning, afternoon and evening sketched for every day, events dropped in, emailed to you. 
Step 3 · CostTrip Cost CalculatorFerry, beds with the rooms tax, meals, getting around and activities in one price range. Our own footage from Vineyard Haven.
Halloween itself is Saturday, October 31, 2026, and that is the day the Oak Bluffs Association has set for Halloween in OB. Also confirmed for the 31st: Halloween on the Hill at the Martha’s Vineyard Museum (4:30 to 6 PM), the West Tisbury library party (2 to 4 PM) and evening hours with cider and candy at the Vineyard Haven library (5 to 8 PM). Before that come the haunted Edgartown walking tour on October 22 and Circuit Arts’ Halloween revue at the Grange Hall, October 27 to 31. Edgartown’s Happy Haunting is on Sunday, October 25, 10 AM to 1 PM. Vineyard Haven’s puppet parade is set for 4 PM on Halloween; the Ag Hall and Chilmark parties are not announced for 2026 yet.
By long tradition, William Street in Vineyard Haven. In 2025 the puppet parade left the Mansion House at 4 PM, William Street trick-or-treating started at 5:30, and parts of Spring and William Streets were closed to cars until about nine. In 2026 the parade is again at 4 PM on the 31st; the street details are not posted yet. Oak Bluffs is the other big one: shop-to-shop trick-or-treating during Halloween in OB (set for October 31 this year) and, in 2025, Vineyard Avenue closed to cars from 4 to 8 PM on Halloween night for the door-to-door crowd.
Yes: Martha’s Vineyard Screenprinting at 426 State Road in Vineyard Haven has been running a haunted house since 2019, benefiting the Tisbury Fire Department. For 2026 it runs Friday and Saturday, October 30 and 31: kid-friendly spooks from 4 to 5:30 PM, then lights-out horror from 7 to 10 PM, $10 for adults and $5 for children 10 and under. For a different kind of fright, the Haunted Edgartown ghost walks are confirmed through October 31.
Yes: the island is in peak color, rooms are 40 to 60 percent below August, the ferry has room and the towns put on a week of free events. It is the off-season, so plan meals around the year-round restaurants and check what is open.
Most of them. Confirmed free for 2026: Halloween on the Hill (donations welcome), the West Tisbury library party and the Vineyard Haven library’s Halloween evening. The street trick-or-treating, the parades and Happy Haunting have been free in past years. Ticketed: the haunted Edgartown walks ($30) and Circuit Arts’ revue at the Grange Hall ($25); the haunted house charges $5 to $10, and the Ritz costume party was a bar night for adults.
The 2026 events were checked on October 2 and again on October 6, 2026 on the organizers’ own pages: the Oak Bluffs Association and the Oak Bluffs town calendar, the Martha’s Vineyard Museum, the Vineyard Preservation Trust, Haunted Edgartown, Circuit Arts, and the West Tisbury and Vineyard Haven libraries. Visit Edgartown, Visit Vineyard Haven, the Chamber of Commerce, the Agricultural Society and The FARM Institute had not posted 2026 Halloween dates yet. The haunted house details are from Martha’s Vineyard Screenprinting’s 2026 poster on its own site, checked October 13. The PA Club dance party is from the event flyer posted by Galaxy Gallery on Instagram, checked October 13. Past-year details are from the Vineyard Gazette’s Halloween coverage of October 2024 and October 2025, its 2024 calendar listing for Halloween in Oak Bluffs and the Martha’s Vineyard Times. Ferry fares and dates are the Steamship Authority’s 2026 schedule. We update this page as the towns post.
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The Chappy Ferry costs $5/person round-trip and $17 for a car with driver. Cards work at the Edgartown-side kiosk; bring cash for the boat itself.
Martha's Vineyard in December 2026: First Friday on December 4, Light Up Oak Bluffs on December 5, Christmas in Edgartown December 10 to 13, 4:15 sunsets, one ferry into Vineyard Haven, and what stays open through Christmas.
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New Year's Eve on Martha's Vineyard: the $150 dinner over the lit harbor, the two-seating table in Edgartown, live music at the Ritz, the family First Night at the Playhouse, where the lights are, what runs on the holiday (the ferry does, the reservation office does not), what is open on New Year's Day, and the empty January that begins the week you leave. 2026–2027 dates.
Columbus Day (Indigenous Peoples' Day) weekend on Martha's Vineyard: the last weekend of the seasonal island. The Artisans Fall Festival at the Grange Hall, the Derby weigh-ins, the last Ocean Park concert, what closes on the Monday (Island Queen, Seastreak, the Chappy gatehouses, the carousel), what stays open, the half-price rooms, and a Friday-to-Tuesday plan.
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