1985:
- Bass were excluded from the Martha’s Vineyard Striped Bass and Bluefish Derby (continued for seven years).
- Cable TV came to the Vineyard.

1986
- Martha’s Vineyard Land Bank Commission was created.

1987
- Wampanoag Tribe gained federal recognition.

1988
- Tisbury didn’t renew moped rental licenses for businesses in Vineyard Haven; Oak Bluffs renewed theirs without public discussion.

1990
- After 110 years in business, the Tilton Lumber Company closed.

1991
- Hurricane Bob hit on August 19.
- First of five state championships for Vineyard football in time line (1991, 1992, 1997, 1999, 2003).

1992
- Edgartown celebrated its 350th anniversary, marking the settlement of the Island by the Mayhews, and West Tisbury celebrated its centennial.

1993
- President Clinton and family’s first of many vacations.

1994
- Princess Diana vacationed here.
- Agricultural Hall in West Tisbury was raised in November, and the Ag Fair moved from the Grange Hall.

1995
- Lots of construction: at the high school,  Oak Bluffs School, West Tisbury School, and the Steamship Authority’s terminal  in Vineyard Haven.

1996
- January blizzard dumped twenty inches of snow and there was a record sixty-one inches of rainfall.

1997
- Taxpayers said no to an Oak Bluffs golf course.
- Polly Hill Arboretum opened.

1998
- Habitat for Humanity purchased its first parcel of land.
- Gay Head officially became Aquinnah.

1999
- JFK Jr.’s airplane crashed off the south shore.

2000
- Tularemia outbreak with fourteen cases confirmed and one death.

2001
- Destroyed by fire: the Tisbury Inn and the Corbin-Norton house on Ocean Park.

2002
- High school added  Portuguese to its course offerings.

2003
- Blinker became a four-way stop at Barnes Road and Edgartown–Vineyard Haven Road.
- Skatepark opened next to the ice arena.

2004
- Red-footed falcon showed up in Katama – first spotting in western hemisphere.

2005
- Jawsfest marked the thirtieth anniversary of the movie.

2006
- Martha’s Vineyard Hospital became affiliated with Massachusetts General and the Martha’s Vineyard Commission approved plans for a new building.

2007
- Breach at Norton Point made Chappaquiddick an island in April.
- Islander made its final run and the Island Home went into service.

2008
- Moujabber garage, built without an appropriate permit in 2003, was torn down in Oak Bluffs.

2009
- Obamas vacationed at Blue Heron Farm.