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Local Oak Bluffs, MA Events & Happenings

  Things to do in Oak Bluffs, MA  

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Full Martha's Vineyard Island Bus Tour
Our Full Island Bus Tour travels through all six Martha's Vineyard towns and takes approximately two and a half hours, including a 30 minute stop at the majestic Aquinnah cliffs. Sit back, relax, and see what makes Martha’s Vineyard one of the most beloved summer destinations in one of our signature buses. A MV Sightseeing bus tour is the perfect introduction to Martha’s Vineyard, while enjoying a leisurely, comfortable ride. Learn local history, and insider information from our knowledgeable bus drivers. Tours leave daily at 9:30am, 10:30am, 11am, 12pm, 1pm, 2:30pm, and 3:30pm, seven days a week through October 14th. See ticket information for details. For questions call 508-693-1555.

When: Sep 17, 2019 9:30AM in Oak Bluffs, MA
Johnny Hoy and the Bluefish
Wednesday night at the Ritz all year long!

When: Sep 18, 2019 8pm in Oak Bluffs, MA
4th Annual Martha's Vineyard Craft Beer Festival
Join us for the 4th Annual Martha's Vineyard Craft Beer Festival. The festival will feature a variety breweries ranging from Island produced to the west coast and abroad.

When: Sep 21, 2019 12:30PM to Sep 21, 2019 7pm in Oak Bluffs, MA
Martha's Vineyard Island Trolley Tour
Our Trolley Tour travels through four Martha's Vineyard towns (Oak Bluffs, Vineyard Haven, Edgartown & West Tisbury) and takes approximately two and a half hours, including a one hour stop in downtown Edgartown. Our air conditioned vintage trolleys are a great way to explore Martha's Vineyard in style. Step aboard and step back in time, and see what makes Martha’s Vineyard one of the most beloved summer destinations.  A MV Sightseeing trolley tour is the perfect introduction to Martha’s Vineyard, while enjoying a leisurely, comfortable ride. Learn local history and insider information from our knowledgeable bus drivers. Tours leave daily at 11am and 2:30pm, seven days a week, through October 14th. See ticket information for details. For questions call 508-693-1555.

When: Oct 13, 2019 9:30AM in Oak Bluffs, MA
Martha's Vineyard Island Trolley Tour
Our Trolley Tour travels through four Martha's Vineyard towns (Oak Bluffs, Vineyard Haven, Edgartown & West Tisbury) and takes approximately two and a half hours, including a one hour stop in downtown Edgartown. Our air conditioned vintage trolleys are a great way to explore Martha's Vineyard in style. Step aboard and step back in time, and see what makes Martha’s Vineyard one of the most beloved summer destinations.  A MV Sightseeing trolley tour is the perfect introduction to Martha’s Vineyard, while enjoying a leisurely, comfortable ride. Learn local history and insider information from our knowledgeable bus drivers. Tours leave daily at 11am and 2:30pm, seven days a week, through October 14th. See ticket information for details. For questions call 508-693-1555.

When: Oct 14, 2019 9:30AM in Oak Bluffs, MA
La Bella Vita – An Italian-themed Dinner and Cocktail Pairing
Join Jonathan Pogash, creator and owner of The Cocktail Guru, and editor of the world famous "Mr. Boston Bartenders' Guide 75th Anniversary Edition", and Hal Ryerson, Chef/Owner of Sweet Life Cafe, for a multi-course dinner and cocktail pairing. If you like Italian ingredients, and “La Bella Vita”, then this dinner is for you. Jonathan will guide you through iconic Italian spirits, Amaris, and Aperitivi, paired exceptionally well with some of Hal’s specialty dishes at Sweet Life.

When: Oct 24, 2019 6pm in Oak Bluffs, MA
Donkey & Goat Wine Dinner
Join us for an engaging dinner featuring the natural, fashionable wines of Donkey & Goat Winery, presented by owners, Jared and Tracey Brandt. These wines will be thoughtfully paired with a 5-course dinner, prepared by Sweet Life Café’s Hal Ryerson, showcasing the best in what Mart[...]

(508) 696-0200

When: Oct 25, 2019 7pm in Oak Bluffs, MA
Cost: $150
Gordon Lightfoot
When: Jul 18, 2020 8pm in Oak Bluffs, MA
The 18th Run&Shoot Filmworks Martha's Vineyard African American Film Festival
The Run&Shoot Filmworks Martha's Vineyard African American Film Festival also known as"The Summer's Finest Film Festival" is now entering its 18th year on Martha's Vineyard.  They have screened and promoted some of the most outstanding and emerging Feature, Documentary and Short films produced by and starring African Americans from across the world.  All screenings and events take place at Martha's Vineyard Performing Arts Center (MVPAC) located adjacent to Martha's Vineyard Regional High School at 100 Edgartown-Vineyard Haven Road - THERE ARE NO REFUNDS

When: Aug 7, 2020 11am in Oak Bluffs, MA