History of Hotelito Oso

At the heart of Circuit Avenue, tucked into the rhythm of downtown Oak Bluffs, the building now known as Oso has been quietly reinventing itself for more than 130 years. Long before boutique clothing, curated playlists, and summer crowds carrying iced coffees wandered through its doors, 33 Circuit Avenue was built for something much more essential: groceries, gossip, and community.

Constructed in 1894 by local businessman John Look, the building originally housed the Look & Washburn Co. Novelty Market — one of the many small independent grocery stores that once fed the island before the rise of national chains. Designed by architect Eli A. Lighton, the building carried a softened version of the whimsical “Carpenter Gothic” style that defines so much of Oak Bluffs. Decorative trim, textured shingles, and just enough flair to remind you that even practical buildings on Martha’s Vineyard were expected to have personality.

Back then, there were no shopping carts, fluorescent aisles, or self-checkout machines. Customers stood at the counter and handed their orders to a clerk, who gathered canned goods from shelves and scooped flour, sugar, or grain from barrels by hand. The building wasn’t just a store — it was a daily meeting place, a neighborhood newsroom, and probably the source of half the island rumors circulating at the time.

Over the decades, the building evolved alongside Oak Bluffs itself. It became Phillips Market under English immigrant Rueben Phillips, later operated as Central Market through much of the mid-20th century, and eventually transformed again when Stanley Brown purchased it in 1963 for the W.S. Brown Insurance Agency. Like many Vineyard buildings, it never stayed frozen in one identity for too long — it adapted, survived, and kept serving the street in whatever way the next generation needed.

Then came one of its most beloved chapters: Laughing Bear, the eclectic clothing store created by artist and designer Annie Schwenk. The building shifted from groceries and insurance policies to color, fabric, creativity, and style — a transformation that felt perfectly suited for Circuit Avenue’s evolving spirit.

In 2024, the building entered its newest era when Erin Tiernan purchased the property and reimagined the space as Oso — Spanish for “bear” — a respectful nod to Laughing Bear while pushing the story into a new generation. Today, Oso blends the old soul of Oak Bluffs with a sharper, more curated energy: part boutique, part conversation piece, part living artifact of downtown Martha’s Vineyard itself.

Because that’s the thing about great Vineyard buildings: they never really stop becoming.