You may think you know the Vineyard, and then you take advantage of a special event like the Cottagers’ 35th Annual House Tour, and you realize there’s a whole world of discovery waiting for you. This year’s event, which takes place on Thursday, July 19 from 10 a.m. to 3 p.m., features six homes that give peeks of streets and homes you may not have known existed as well as some with grand historical significance.

26 Wayland avenue is also on the tour. — Jeanna Shepard

The Cottagers, which sponsors the tour, is a philanthropic organization consisting of 100 women of color who are property owners on Martha’s Vineyard. Their mission is to raise money for local charities and organizations through a variety of fundraising efforts. This year is their 62nd in operation.

The House Tour is always a sellout, so you are advised to buy your tickets early. Recipients of The Cottagers’ largess include Windemere Nursing and Rehabilitation Center, Oak Bluffs Police Department, Oak Bluffs Public Library, plus selected programs for women and nonprofit agencies.

Advance tickets may be purchased in Oak Bluffs at the Cousen Rose Gallery and C’est La Vie, both on Circuit avenue. Tickets may also be purchased on the day of the tour at Cottagers’ Corner on 57 Pequot avenue from 9 a.m. to 1 p.m. The cost is $35 per person. Visit for more information.

17 Thompson Avenue


17 Thompson avenue. — Jeanna Shepard

Thompson avenue is one of those tight little dirt roads that doesn’t see much activity unless it’s a property owner coming home. At number 17, you’ll find a neatly kept two-story, shingle-style house with a farmer’s porch and a countenance that echoes the Victorian era of Oak Bluffs homes.

The home is just a few streets over from famed Shearer Cottage. All three owners are graduates of Hampton University as were Charles and Henrietta Shearer and take great pride in their association with both the university and the Shearers.

6 Coral Avenue


6 Coral avenue. — Jeanna Shepard

Built in 2016, this shingle-style home brings some modernity to the Shearer Cottage area. Its open-concept design allows for residents and guests to flow from the kitchen to the dining room to the living room and to the outside. A finished basement provides even more room for entertaining.

Of special note is the extensive landscaping which features a privacy wall of trees along the back side of the property to allow space for a relaxing hammock and Adirondack chairs. Keep your eyes out for a beautiful retaining wall and hydrangeas planted along the front of the property.

29 Laurel Avenue


29 Laurel avenue. — Jeanna Shepard

You’ll recognize this 153-year-old gem by its distinctive Second Empire/Mansard roof and lovely side-yard embraced by blue hydrangeas and a white picket fence.

Its Vineyard pedigree is underscored by the Massachusetts Historical Commission which noted that “it may be one of the oldest houses standing in the Vineyard Highlands.” Add in the reference that it is also known as the TC Luce House, and the Island lineage is complete.

42 Nashawena Park


42 Nashawena Park. — Jeanna Shepard

The bronze plaque attached to the front of this seaside resort, shingle-style home proclaims that Sen. Edward Brooke purchased it in 1958 and named it the Island Club. He wanted to establish a Martha’s Vineyard club that black people could call their own.

Senator Brooke’s many accomplishments in public service helped make the home a must-stop on the Vineyard’s African American Heritage Trail. A swimming pool, warp-around covered porches, fireplaces and many architectural features make it a worthy stop on the Cottager Tour, too.

10 Pequot Avenue


A beautiful makeover in 2016 transformed this High Victorian-style home built in 1870 from a forgotten misfit into a modern oasis that still exudes a cottage vibe.

Porch living is very much the lifestyle here on its wrap-around porch where the family gathers and guests are entertained. The beach is just three houses away.