Don't miss out on the best live jazz experiences in the area!

Our Summer Events Calendar

Explore our curated list of jazz events happening from June 9 – August 30

Our Featured Event...

A Different Kinda Entertainment

Experience an unforgettable evening celebrating the timeless music and romantic legacy of Luther Vandross. Vandross on the Vineyard features acclaimed vocalist Darnell Alexander, whose smooth, soulful sound brings new life to the songs that defined generations.

Presented by Alldat Jazz! Live Jazz Experiences, this special Sunday Evening Jazzy Jam Showcase combines powerful vocals, live musicianship, elegant island energy, and the intimate atmosphere of the historic Strand Theatre in Oak Bluffs.

Join us for a 5:00 PM Happy Hour before the showcase begins at 6:00 PM. Whether you are a lifelong Luther Vandross fan or simply love exceptional live music, this will be one of Martha’s Vineyard’s most memorable nights of the summer.

Sunday, August 9, 2026
Happy Hour: 5:00 PM
Showcase: 6:00–9:00 PM
The Strand Theatre
Oak Bluffs, Martha’s Vineyard

Live jazz. Iconic music. An unforgettable Vineyard experience.

Supporting Local Artists

Frank Wilkins is a renowned international pianist, music director, educator, and cultural icon whose expansive career spans continents, genres, and generations. He has performed with legendary artists including George Duke, Esperanza Spalding, Angela Bofill, Phyllis Hyman, and Tiger Okoshi, and has opened for iconic acts such as Sly and the Family Stone, The Whispers, Gladys Knight, The Manhattans, The Spinners, and Ray Charles.
His performance career includes premier venues and festivals such as Scullers Jazz Club, Ryles Jazz Club, House of Blues Boston, Newport Jazz Festival, Montreux Jazz Festival, and Toulon Jazz Festival. A founding musician of Boston’s annual John Coltrane Festival, Frank has shared his artistry globally, including in Qatar, France, Mexico, Switzerland, Holland, and West Africa.
A prolific artist, he has performed, arranged, and produced over 60 recordings. He is the founder of the WeJazzUp Trio and creator of the long-running Frank Wilkins Vocal Showcase at Slade’s Bar & Grill. A dedicated educator, Frank has served as an adjunct professor at Berklee College of Music, Tufts University, New England Institute of Art, Northeastern University, and Roxbury Community College. He is a graduate of Berklee College of Music and the Wisconsin Conservatory of Music

The Strand Theatre

The Strand Theatre is a beautifully restored, historic 210-seat vintage entertainment venue located at 11 Oak Bluffs Avenue in Oak Bluffs, MA 02557 on Martha’s Vineyard. Originally opened in 1915, the theater has been brought back to life under the operator care of Steve Capers, transforming from a traditional summer movie house into a multi-use community hub that hosts comedy shows, live music, film screenings, and private events.

Meet Darnel Alexander

Darnel Alexander is a Minneapolis-based R&B singer and fitness trainer who rose to prominence in the 1990s with the quartet 2nd Nature before achieving viral international fame as “The Voice of Luther” covering Luther Vandross. Currently, he balances a global solo performing career with releasing independent music and professional bodybuilding. For more information, search for Darnel Alexander’s official profiles.

Martha's Vineyard - The Lights Are Still On

Oak Bluffs, Massachusetts, is widely recognized as America’s premier African American summer mecca and cultural sanctuary. Located on the northeast shore of Martha’s Vineyard, the town evolved from a 19th-century religious campsite into a vibrant haven for Black wealth, creativity, and community. During the Jim Crow era, while most resort towns strictly segregated Black travelers, Oak Bluffs stood out as a welcoming enclave where African Americans could purchase property, build businesses, and vacation in safety

Vandross on the Vineyard - feat Darnel Alexander

Experience an unforgettable evening celebrating the timeless music and romantic legacy of Luther Vandross. Vandross on the Vineyard features acclaimed vocalist Darnell Alexander, whose smooth, soulful sound brings new life to the songs that defined generations.

Presented by Alldat Jazz! Live Jazz Experiences, this special Sunday Evening Jazzy Jam Showcase combines powerful vocals, live musicianship, elegant island energy, and the intimate atmosphere of the historic Strand Theatre in Oak Bluffs.

Join us for a 5:00 PM Happy Hour before the showcase begins at 6:00 PM. Whether you are a lifelong Luther Vandross fan or simply love exceptional live music, this will be one of Martha’s Vineyard’s most memorable nights of the summer.

Sunday, August 9 and Aug 30, 2026
Pre-Show Social Hour: 5:00 PM
Showcase: 6:00–9:00 PM
The Strand Theatre
Oak Bluffs, Martha’s Vineyard

Aug 9 and Aug 30 2026

STARTING AT $69

Jazz+

Jazz+ is a dynamic trio jazz band that seamlessly blends traditional jazz with smooth contemporary styles, offering a captivating musical experience. With a refined sound rooted in jazz standards and a modern flair, they cater to diverse audiences and occasions. Whether performing at intimate venues or lively events, Jazz+ delivers soulful performances that evoke both nostalgia and innovation.

The Saturday Supper Club is the monthly grown and sexy high energy event the triangle has been looking for! Live jazz, great food ( featuring a Mediterranean menu with grilled shish kabobs on August 10), artisan crafted drinks from our open bar, art, magic, and comedy. 

STARTING at $59

Jazz The Lake - Falls Lake

Pack your coolers and picnic baskets. You are about to experience a cruise with beautiful views and LIVE smooth jazz performed by local artists on a pontoon boat.


Bring your friends/family or come to meet new friends. Don’t forget your sunglasses, sundresses and seersucker shorts.

Celebrating a special occasion? Ask about our Romantic Cruises, and customized private cruises.

Weekly starting Sept 6

$99

JazzBiz Afterhours - Wake Forest

This is where work and play meet! Build your brand, strengthen your team, or meet new clients—while jazzin and toasting. After hours business and social networking for the modern day professional featuring live jazz!

Late Summer 2026

FREE

A Grown, Sexy, and Jazzy Prom

Feb 13, 2027 - Save the Date!

Don’t miss out on this amazing black tie affair