Island Events Calendar
From the Ag Fair and Illumination Night to Christmas in Edgartown, these are the island’s signature events — with a one-click link to check availability at the Inn for each one. Oak Bluffs events are a short walk from your door.
Fall & Holidays 2026
- Oct242026Book These Dates
Living Local Harvest Festival
Island farmers, food makers and artisans fill the Ag Hall for a free celebration of the fall harvest.
Event details: MV Agricultural Society ↗ - Oct312026Book These Dates
Halloween in Oak Bluffs
Costumes, trick-or-treating on Circuit Avenue and a town-wide party just steps from the Inn.
Event details: Oak Bluffs Association ↗ - Nov72026Book These Dates
Barn Raisers Ball
The Ag Society’s annual barn dance at the Ag Hall, held the first Saturday of November.
Event details: MV Agricultural Society ↗ - Nov26–282026Book These Dates
Thanksgiving Weekend on the Vineyard
Oak Bluffs Turkey Trot (Thu), the Vineyard Artisans Thanksgiving Festival at the Ag Hall (Fri–Sat) and the Chowder Cup in Edgartown (Sat).
Event details: Visit Edgartown ↗ - Dec52026Book These Dates
Light Up Oak Bluffs
Tree lighting, carolers and holiday shopping around Healey Square and Ocean Park. Vineyard Haven’s ‘Tis the Season First Friday is the night before.
Event details: Oak Bluffs Association ↗ - Dec10–132026Book These Dates
Christmas in Edgartown (45th)
Four days of lighthouse lighting, the Saturday parade, Teddy Bear Suite, house tours and shopping strolls.
Event details: christmasinedgartown.com ↗ - Dec312026Book These Dates
New Year’s Eve
Ring in 2027 with dinners and live music in Oak Bluffs, Edgartown and Vineyard Haven.
Event details: MV Chamber of Commerce ↗
Spring 2027
- Mar62027Book These Dates
Martha’s Vineyard 20 Miler & Amity Island Relay
The island’s winter classic road race and relay — a great excuse for an off-season weekend.
Event details: MV Chamber of Commerce ↗ - Mar–Apr31–42027Book These Dates
Martha’s Vineyard Film Festival (27th)
Circuit Arts’ five-day festival of independent film, filmmaker talks and community meals.
Event details: tmvff.org ↗ - May28–312027Book These Dates
Memorial Day Weekend
The unofficial start of the season — beaches, the Vineyard Artisans Memorial Day Festival and the first farmers markets.
Event details: MV Chamber of Commerce ↗
Summer 2027
- Jun102027Book These Dates
A Taste of the Vineyard: Gourmet Stroll
The Vineyard Trust’s signature evening of island chefs, wine and music on the lawn of the Dr. Daniel Fisher House. Typically the second Thursday of June.
Event details: Vineyard Trust ↗ - Jun122027Book These Dates
Pride on Island Parade
The island’s Pride parade runs from the ferry terminal to Ocean Park, right past the Inn’s neighborhood.
Event details: MV Chamber of Commerce ↗ - Jun192027Book These Dates
Oak Bluffs HarborFest
Music, food vendors and family fun along Oak Bluffs Harbor, coinciding with Juneteenth celebrations.
Event details: Oak Bluffs Association ↗ - Jul3–42027Book These Dates
Edgartown Fourth of July Parade & Fireworks
The 5 pm parade down Main Street followed by fireworks over Edgartown Harbor at dusk.
Event details: Visit Edgartown ↗ - Jul82027Book These Dates
Tisbury Street Fair
Main Street closes for the town’s birthday block party — food, crafts and live music.
Event details: MV Chamber of Commerce ↗ - Jul17–182027Book These Dates
Feast of the Holy Ghost
The Portuguese-American Club’s beloved summer feast with free sopa, music and a Sunday procession.
Event details: MV Chamber of Commerce ↗ - Jul25–312027Book These Dates
Legacy Week on the Vineyard (HBCU Week)
A week of alumni gatherings, panels, concerts and the Gospel House Brunch celebrating HBCU legacy on the Vineyard.
Event details: legacyweekonthevineyard.com ↗ - Aug6–142027Book These Dates
Martha’s Vineyard African American Film Festival (25th)
Nine days of premieres, panels and parties at the MV Performing Arts Center. 2027 dates to be announced; typically the first two weeks of August.
Event details: mvaaff.com ↗ - Aug7–82027Book These Dates
Possible Dreams Auction
MV Community Services’ celebrity-studded benefit auction at Allen Farm. 2027 date to be announced; typically the first or second weekend of August.
Event details: MV Community Services ↗ - Aug12–152027Book These Dates
Martha’s Vineyard Agricultural Fair (165th)
Four days of livestock, rides, the woodsmen’s contest, fair food and fiddle music at the fairgrounds.
Event details: MV Agricultural Society ↗ - Aug182027Book These Dates
Grand Illumination Night
Thousands of paper lanterns light the Campground cottages after a Tabernacle sing-along. Held the Wednesday after the Ag Fair; 2027 date pending MVCMA announcement.
Event details: MVCMA ↗ - Aug20–212027Book These Dates
Oak Bluffs Fireworks
The summer-ending fireworks over Ocean Park return in 2027 after the 2026 weather cancellation. Date pending town announcement; typically the Friday after Illumination Night.
Event details: Oak Bluffs Association ↗ - Sep3–62027Book These Dates
Labor Day Weekend
Last big beach weekend of the season, with the Vineyard Artisans Labor Day Festival at the Ag Hall.
Event details: MV Chamber of Commerce ↗
Fall & Holidays 2027
- Sep–Oct12–162027Book These Dates
MV Striped Bass & Bluefish Derby (82nd)
Five weeks of surf and boat fishing with nightly weigh-ins on Dock Street in Edgartown. 2027 dates pending; typically mid-September to mid-October.
Event details: mvderby.com ↗ - Sep182027Book These Dates
Tivoli Day
Circuit Avenue’s end-of-summer street fair with vendors, music and the Tivoli Day road race.
Event details: Oak Bluffs Association ↗ - Oct232027Book These Dates
Living Local Harvest Festival
The Ag Society’s free fall harvest celebration. Typically the fourth Saturday of October.
Event details: MV Agricultural Society ↗ - Oct312027Book These Dates
Halloween in Oak Bluffs
Costumes and trick-or-treating on Circuit Avenue.
Event details: Oak Bluffs Association ↗ - Nov62027Book These Dates
Barn Raisers Ball
The Ag Society’s annual barn dance, held the first Saturday of November.
Event details: MV Agricultural Society ↗ - Nov25–272027Book These Dates
Thanksgiving Weekend on the Vineyard
Oak Bluffs Turkey Trot, the Vineyard Artisans Thanksgiving Festival and Edgartown’s Chowder Cup.
Event details: Visit Edgartown ↗ - Dec42027Book These Dates
Light Up Oak Bluffs
Tree lighting and holiday festivities around Healey Square and Ocean Park. Typically the first Saturday of December.
Event details: Oak Bluffs Association ↗ - Dec9–122027Book These Dates
Christmas in Edgartown (46th)
Lighthouse lighting, Saturday parade and holiday strolls. 2027 dates pending; typically the second weekend of December.
Event details: christmasinedgartown.com ↗
Event dates are published by each organizer and can change. Booking links pre-fill the event dates in our reservation system — adjust your arrival and departure before you check availability. Questions about planning your stay around an event? Call us at 508-693-2002.