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Flags in a crowd in Edgartown. The town’s Memorial Day observance is a students’ parade down Main Street, with a bouquet laid at the memorial outside the courthouse.
Memorial Day weekend on Martha's Vineyard, explained: the Friday March to the Sea at Owen Park, the Monday parade in Vineyard Haven, the Artisans Festival at the Grange Hall, the first Island Queen and Gay Head Light climbs, what is still closed, the prices, and a three-day plan for May 29 to 31, 2027.
Memorial Day weekend is the day the island switches on. The Steamship boats have just started landing in Oak Bluffs, the Island Queen makes its first Falmouth run on the Friday, the last wave of seasonal restaurants unlocks its doors, the Gay Head Light opens for climbing, and the towns hold their Memorial Day observances, with schoolchildren walking to the harbor to throw flowers into the water. It is also the cheapest weekend of the season to be here, with the ocean still too cold to swim and the lifeguards a month away. In 2027 the weekend runs Saturday, May 29 to Monday, May 31. This is what runs, what doesn't yet, and how the three days usually go.
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The island’s Memorial Day begins on the Friday, at lunchtime, in Vineyard Haven. Around 300 Tisbury School students leave the school at 12:15 PM and walk down Spring Street and Main Street to Owen Park, each carrying a flower. At the pier the band plays, the anthem is sung, Taps is played, and the students throw their flowers into the harbor one at a time, each one for a service member a family lost, while the crowd on the lawn goes silent. The ceremony takes about 45 minutes; the microphone is in the bandstand, so the crowd faces that way. In 2026 the Chilmark, Edgartown and Oak Bluffs schools held their own marches to the water the same day, and Edgartown’s students paraded down Main Street after a bouquet was laid at the memorial outside the courthouse. If you are on the island that Friday, it is worth seeing. The crowd stands back and keeps quiet during the flowers, and the children have the pier.
The pier at Owen Park in Vineyard Haven, where the Tisbury School march ends and the flowers go into the harbor.
Know Before You Go
The season’s first big makers’ market, Saturday and Sunday of the weekend, 10 AM to 4 PM at the Grange Hall in West Tisbury. Free. More than a hundred island artists and makers.
The Martha’s Vineyard Garden Club sells island-grown plants at the Old Mill in West Tisbury over the weekend. The good perennials tend to go in the first hour.
Mytoi on Chappaquiddick is at its best in late May, $10 in season. Polly Hill Arboretum’s visitor center opens for the weekend; the grounds have been open all along.
The Gay Head Light’s first climbs of the year. The Chappaquiddick ferry goes onto summer hours the Thursday before the holiday, so the Chappy side is reachable all evening.
The Flying Horses in Oak Bluffs opens on weekends in spring before its summer schedule, about $5 a ride, the oldest platform carousel in the country.
A community dance in 2025 on the wide plank floor of an old timber hall. Over Memorial Day weekend the Vineyard Artisans Festival sets up its tables in the Grange Hall in West Tisbury.
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The parade is on the Monday morning, and it is a small-town one. It steps off at 10:30 AM from American Legion Post 257 at 47 Martin Road in Vineyard Haven and walks to the Avenue of Flags at Oak Grove Cemetery, where the ceremony is held among the graves with veterans from nearly every branch. In 2026 rain and fog moved it indoors to the Tisbury School gym; the speaker was the county’s veterans services officer, and more than 20 veterans stood for the roll. It is a small ceremony and the reason for the weekend, and visitors are welcome to stand with the town.
An American flag on a yardarm mast under a gray sky. On Memorial Day the flag flies at half-staff through the morning.
Know Before You Go
53 to 55 degrees: lovely for a walk, very cold for a swim. The water passes 65 in July.
None until late June at the big beaches. Owen Park and State Beach are the calm choices for children this weekend.
Many beach dog limits are already on by Memorial Day: State Beach and Norton Point since April 1, Oak Bluffs town beaches (daytime) since May 15, and they run into September. Lobsterville and Fuller Street stay open to leashed dogs all summer.
The West Tisbury market opens the first Saturday of June (June 6 in 2026), not this weekend. The Grange Hall festival is the market that weekend.
Highs are usually in the 60s and a cold wind off the water can undo a sunny forecast; in 2026 rain and fog moved the parade indoors. A warm layer and a rain plan help.
The stair inside the Gay Head Light. The tower opened for climbing on Memorial Day weekend 2026, its first full season since the 2024–25 lantern restoration.
We would come over on foot on the Friday morning boat, be at Owen Park by 12:30, and sleep in Vineyard Haven or Oak Bluffs so the bus does the rest. Saturday, take the bus up-island for the Grange Hall festival and the plant sale, then on to Aquinnah for the first lighthouse climb of the year and the cliffs at sunset. Sunday, Chappaquiddick: the ferry is on summer hours, Mytoi is at its greenest, and the beach at Wasque is empty. Monday, the parade at 10:30, a late lunch, and the afternoon boat home. Our May guide has the prices and openings week by week, the spring guide covers April, and the June guide is what happens next.
A garden in full green under a blue sky, a tall drooping evergreen above a stone path.
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 and Oak Bluffs.
Yes, for everything but swimming. Nearly every seasonal business is open, the rooms are far below August rates, the bus is free, and the crowds are a fraction of July’s. The ocean is 53 to 55 degrees and there are no lifeguards until late June.
Yes. The parade steps off at 10:30 AM on the Monday from American Legion Post 257 on Martin Road in Vineyard Haven and walks to Oak Grove Cemetery for the ceremony. On the Friday before, the Tisbury School’s March to the Sea ends at Owen Park with students throwing flowers into the harbor.
Saturday, May 29 to Monday, May 31, 2027. The Tisbury School march is on Friday, May 28, if it follows its usual pattern; check the school and the town calendars in May.
For a car, yes, and holiday weekend slots sell out months ahead at $168 each way. Walk-on passengers never need one: $11 each way on the Steamship, or $20 on the Island Queen from Falmouth, which starts that Friday.
Almost everything: the seasonal restaurants, the Aquinnah shops, the Gay Head Light, the Chappy ferry on summer hours, the Flying Horses, Mytoi and Polly Hill. Not yet: lifeguards, the West Tisbury Farmers Market and the East Chop Light sunset tours, all of which start in June.
The March to the Sea details are from the Tisbury School’s 2026 notice and the Martha’s Vineyard Times and Vineyard Gazette reports of May 22 and May 25, 2026; the parade route and time are from the American Legion Post 257 listing. Ferry fares and start dates are the operators’ published 2026 schedules; lodging figures are from our where-to-stay research; restaurant openings from the businesses’ own 2026 announcements. The 2027 dates are the calendar. Check the events calendar before you travel; island dates move.
Island tip of the day Shopping No. 31 of 86 New tip at midnight, island time
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.
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).
The Hamptons or Martha's Vineyard? A New York scene two to three hours away by Jitney or train, with ocean beaches behind a $750 season permit, against a six-town island reached by an hour's flight or a day's train and boat, where thirteen beaches are free to all, the bus is free and the nights are quiet. Getting there, beaches, beds, towns, nightlife, children and cost, honestly.
Newport or Martha's Vineyard? A drivable Gilded Age city with the Breakers ($32), the free 3.5-mile Cliff Walk, festival weekends at Fort Adams and a late harbor front, against a six-town island reached by an $11 ferry with twenty beaches, a free bus and quiet nights. Getting there, sights, beds, nights, children, weddings, and doing both from Rhode Island.
Block Island vs Martha's Vineyard, honestly: a 9.7-square-mile island with one village and a $12 year-round ferry from Point Judith against 96 square miles, six towns and an $11 boat from Woods Hole. Size, ferries (the car fare gap is huge), beds, beaches, the week versus the weekend, and which one fits your trip from Rhode Island.
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.
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