Jeffrey Osborne to headline Cottagers benefit concert in Oak Bluffs

The Cottagers will host a benefit concert with Jeffrey Osborne on July 30 at the Strand Theatre in Oak Bluffs as part of the nonprofit’s 70th anniversary celebration. Proceeds will support the restored Cottagers' Corner and ongoing community programs on Martha's Vineyard.

Why it matters: - The concert will help fund the Cottagers' Corner Restoration and Building Fund. - The event is tied to The Cottagers' 70th anniversary, a milestone for a nonprofit that has supported Martha's Vineyard for decades. - Ticket sales will also help sustain the organization’s charitable, educational and community service work.

What happened: - The Cottagers, Incorporated will host A Soulful Evening with Jeffrey Osborne on Thursday, July 30, 2026, at the Strand Theatre in downtown Oak Bluffs. - Truist Bank is presenting the benefit concert. - Doors open at 7:30 p.m. - The event is part of a series of signature programs marking The Cottagers' 70th anniversary.

The details: - Jeffrey Osborne is a Grammy-nominated singer and songwriter known for hits including On the Wings of Love, Stay with Me Tonight and You Should Be Mine (The Woo Woo Song). - Proceeds will benefit the Cottagers' Corner Restoration and Building Fund. - The fund supports the organization’s newly restored headquarters at 57 Pequot Avenue in Oak Bluffs. - The money will also support ongoing charitable, educational and community service initiatives on Martha's Vineyard. - The recently restored Cottagers' Corner is set to reopen this summer after a renovation meant to preserve its historic character and improve accessibility and year-round use. - VIP tickets and event information are available at the Cottagers' website and at the Strand Theatre box office. - The Strand Theatre is located at 11 Oak Bluffs Avenue in downtown Oak Bluffs.

Between the lines: - The fundraiser pairs a recognizable headliner with a preservation and community mission, which can broaden support beyond longtime members and donors. - The anniversary celebration also reinforces The Cottagers’ long-running role as a civic and cultural anchor in the Island community.

What's next: - The Cottagers' Corner is scheduled to reopen this summer. - The July 30 concert will serve as one of the organization’s key anniversary events. - Additional support from ticket buyers will help finance future service and outreach work.

The bottom line: - The Cottagers are using a major anniversary event to raise money, celebrate history and strengthen a restored community hub.