As a child visiting Martha’s Vineyard every summer, Jason Brown, CEO of Boston-based Blue Flag Capital, got to know Edgartown, Massachusetts, quite well—but the 282-year-old Kelley House hotel was something of a mystery. That property, sitting prominently on the harbor, comprised nine disparate buildings that had seen better days, as well as the iconic Newes From America pub. But aside from the restaurant, Brown says, “I never knew what it was. It was something you walked by.”
It’s no surprise he jumped at the chance to renovate the hotel into Faraway Martha’s Vineyard, the second hotel in Blue Flag’s boho-chic Faraway collection. It joins Faraway Nantucket, which has a similar campus layout, urban-core vibe, and deep sense of local history.
The majority of the 58 guestrooms are spread across the Kelley House (with some housed in five additional buildings), joined by three F&B venues, including the outdoor sushi bar Pelican Club, the Snack Shack poolside bar, and Newes From America.
The transformation of the Kelley House into the Faraway Martha’s Vineyard began with Carly Simon. Brown recalls his boyhood summers listening to the singer, a year-round island resident, performing at the old whaling church or even on the street.
“The idea was, how do we take this very New England Georgian-style architecture of Edgartown, but bring in a muse that will give us freedom on the interiors to be a little more eclectic?” says Andrew Kline, associate principal at New York-based architecture and design firm Workshop/APD, which was charged with reinventing the hotel. “So we started with Carly.”
The architecture—wrapped in the location’s signature shingles—was largely left alone, with a few historically appropriate upgrades. Inside, Kline says, the design team imagined what Simon might bring into an old New England house: “[It would] be a little bit hipper, cooler,” he says. “We wanted to be true to the colors and tones of what a resort in Edgartown would be, with a base layer of elements inspired by the 1950s, ’60s, and ’70s.”
Vintage and modern decorative items mingle in public spaces, while guestrooms feature custom midcentury-inspired furniture and handwoven rugs—“like remnants you might take home from a flea market,” Kline says. “Something that feels like it has history.”
Throughout the interiors, the warm, sandy color scheme and mellow-rock roots are punctuated by floor-to-ceiling drapery that reveals bric-a-brac inside oversized cabinetry. Natural materials and greenery, such as vibrant custom floral pieces, add another layer, Kline says, “bringing in a mystical element, almost like a botanical siren luring you to stay for a long time.”
Brown describes the previous site as a disjointed collection of fenced-off houses around a large parking lot. Improving the guest experience and the hotel’s connection with the town required reallocating functions among the historic buildings, as well as significant upgrades to the outdoor spaces.
The main entrance was given a new façade, awning, and landscaping. Workshop/APD blew out the lobby, doubling its height and transforming what had been two guestrooms behind it into an inviting library that leads to a new central courtyard. The pool, which had awkwardly occupied a front corner of the property, was moved to the courtyard, where a cut-through path traverses the length of the grounds, inviting guests and neighbors to stroll the revitalized space. Lush greenery and soft grasses bring a bit of “up-island” wildness downtown.
“We wanted to center Edgartown—to make this a true [resort] that serves as a connectivity point to the rest of the island,” Brown says. “That was the opportunity, and we want to do our part in being good stewards over the longterm.”
This article originally appeared in HD’s April 2024 issue.