Kickemuit Cottage // 1869

Summer is here and I am missing my favorite place to explore, Oak Bluffs on Martha’s Vineyard. The town is sleepy most of the year, but in the Summer, the place explodes with summer residents and tourists, providing such a lively and diverse atmosphere. One of the most beautiful of the cottages in the Wesleyan Grove campground is the Kickemuit Cottage, built in 1869 for a family from Rhode Island. They so-named the cottage after the Kickemuit River which runs from Massachusetts through Warren, RI and spills out into the Mt. Hope Bay. The story goes that this double cottage was actually just a single peaked home until it was combined with another giving it the double-peaked appearance we see today. The cottage retains the turned posts, delicate gingerbread detailing, and the lancet windows and doors. Swoon!

Side note: If anyone has a cottage in Oak Bluffs that they’ll let me rent, I would love to be in touch!

Villa Rosa // 1875

This Victorian mansion in Oak Bluffs was built in 1875 as part of the Oak Bluffs Land and Wharf Development, a private off-shoot development inspired by the success of the Wesleyan Grove campground. The Stick style house was occupied by wealthy businessmen and their families from its completion to after WWII. The home was purchased by Joe Overton of Harlem, NY, likely the home’s first Black owner. Under Overton’s ownership, Martin Luther King Jr., Adam Clayton Powell Jr. and other civil rights leaders visited what has come to be known as the Summer White House for African Americans. Overton was New York’s first African American labor organizer and president of NAACP New York Chapter. The home served as an informal inn, which provided a safe night’s stay for African American elite visiting the island. There was a guestbook with the signature of nearly every major Civil Right’s organizer in it, even Fidel Castro stayed here once. The home is now owned by Valerie Mosley, who named it after her grandmother as Villa Rosa.

Hills-Claflin House // 1871

This grand home was built in 1871 for George Hills, one of the original investors in the Oak Bluffs Land & Wharf Company development, a development to the east of Wesleyan Grove. The home was designed by Samuel Freeman Pratt, a Boston carpenter turned premier architect of Oak Bluffs, who likely designed the home in his distinct Stick Style with intricate wood carvings and posts. In 1877, the home was purchased by Governor William Claflin after his time in office as a summer retreat from his home in Newton, MA. The governor was an ardent Methodist who was involved with liberal causes such as abolition and Native American and female enfranchisement. Within 10 years of his purchasing of the home, he modified and enlarged it with Colonial Revival motifs including the gambrel roof, Tuscan columned porch, and simplified dormers.

Sea View House // 1872-1892

Oak Bluffs got its start as a resort community when the Martha’s Vineyard Camp Meeting Association began constructing permanent summer cottages in 1860 in the area known as Wesleyan Grove. Due to this success, a couple wealthy men in Edgartown formed the Oak Bluffs Land and Wharf Company, who purchased land adjacent to the Grove, between the Campground and Nantucket Sound. The 75-acre parcel was laid out by Robert Morris Copeland, a Boston landscape architect, who created a system of curvilinear streets and parks, with house lots surrounding each park, in much the same manner as the Campground itself. A few parcels were established for places of worship, but the development wanted to appeal to other religions as the Methodists already had an entire development, from this the 1870 Union Chapel, designed by Samuel Freeman Pratt, was the first built. Another anchor of the development was to be a large luxury resort.

At the head of the Steamship Wharf, the Company built one of the most spacious and luxurious resort hotels of its time, the Sea View House. When it was completed in 1872, the Sea View House was the symbol of the Company’s success. The Sea View was built at a cost of $102,000 with a further cost of $30,000 in furnishings; five stories high on the waterside and four on the inland elevation, it measured 225 feet in length and 40 feet in depth. It contained 125 rooms, office, parlor, spacious dining salons and reception suites. Speaking tubes connected every room with the office; the whole hotel was lit by gas, and warmed by steam heat. The hotel was the first thing seen by new visitors disembarking from the steamers onto the island. The hotel was designed by the same architect as the Union Chapel, Samuel Freeman Pratt. He continued his use of the Stick style for the hotel with elaborate wood framing, trim and Victorian flair. Sadly, on September 24, 1892, the Sea View House caught fire and burned to the ground in less than 40 minutes after the alarm was sounded. The fire originated in the basement near the kitchen, and it was thought resulted from a stray spark getting into the cotton waste that was near the engine.