The Cottagers’ 39th Annual House Tour takes place Thursday, July 16 from 10 a.m. to 3 p.m., rain or shine. The self-guided tour begins at Cottagers’ Corner, located at 57 Pequot avenue in Oak Bluffs, where guests will check in and receive tour materials.

This year’s tour features five Oak Bluffs residences and the newly restored Cottagers’ Corner, the historic headquarters of The Cottagers.

60 Pennacook Avenue

60 Pennacook Avenue — Courtesy Cottagers'

While the original bungalow dates to 1936, the home was thoughtfully rebuilt in 2025 with careful attention to preserving its historic character and relationship to the surrounding neighborhood. But what makes the home uniquely special is the story owner Menonie Parker has woven into every detail.

Throughout the residence, visitors will discover design elements that celebrate Oak Bluffs’ rich African American heritage, including custom wallpaper depicting scenes from 19th-century Oak Bluffs and honoring generations of Black families who helped shape the community. Artwork by Black artists, quilt-inspired designs and treasured textiles reflect Parker’s passion for storytelling and cultural preservation. 42 Paddock Road Nestled within The Preserve, Michael Weir and Mirian Graddick-Weir’s elegant colonial-style residence was designed with gathering in mind. Since purchasing the property in 2020, the couple has transformed the home into an inviting retreat where family and friends naturally come together. A pool, spa, outdoor kitchen, cabana, fire pit, and expansive entertainment spaces encourage connection and celebration.

18 Narragansett Avenue

In the heart of historic Oak Bluffs stands The She Shed, a beloved Victorian cottage owned by Shelley Christiansen.

Purchased in 1984 by Christiansen and her mother, Sheppie Moore, the cottage has been the setting for decades of family memories. Following her mother’s death in 2023, Ms. Christiansen named the home in honor of the start of both their names and the deep bond they shared.   

9 Huntington Avenue. — Courtesy Cottagers

“The She Shed is a tribute to the life we created here,” she said. “Every room holds a memory.”

9 Huntington Avenue

For Tanya Holcomb and Richard Webber, their Highlands-area home serves as both a gathering place and a connection to one of Oak Bluffs’ most historic neighborhoods.

The seven-bedroom residence was designed to welcome family and friends while supporting today’s flexible work-and-travel lifestyle. Yet what Holcomb treasures most is the opportunity to become part of the continuing story of the Vineyard Highlands community.

83 Wing Road

Traci and Shane Sanders have created a home that embraces the relaxed rhythm of Vineyard life. Purchased in 2023 and extensively renovated soon after, the shingle-style residence combines coastal elegance with warmth and hospitality. For the Sanders family, Oak Bluffs offers the perfect blend of natural beauty, cultural richness, and community spirit.

Cottagers' Corner. — Courtesy Cottagers

Cottagers’ Corner, 57 Pequot Avenue

This year’s tour also features one of Oak Bluffs’ most cherished landmarks. Fresh from an extensive restoration, Cottagers’ Corner stands proudly renewed as both a historic building and a vibrant community resource.

Originally constructed in the 19th century as Oak Bluffs’ town hall and fire station, the building has served many purposes throughout its history. Since 1968, however, it has been the home of The Cottagers.

As The Cottagers celebrate a milestone anniversary, Cottagers’ Corner stands as a powerful symbol of the organization’s enduring commitment to service, education, culture, and community.

For tickets and more information visit thecottagersincofmv.org/annual-house-tour.