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  • Writer's pictureJenny Penland

Watch Hill, Rhode Island ‣ We had a marvelous time, ruining everything.

You can't get more "iconic New England" than Watch Hill - and yet, it has somehow remained blissfully off the beaten path. Sitting at the most-southwestern point in all of Rhode Island, Watch Hill became home to a handful of wealthy, victorian families in the late 19th and early 20th century, and has maintained its "old-money summer colony" for several generations since. Just an hour drive up the coast from Newport, the affluent coastal village has a family-oriented, yacht club feel. It's walkable and intimate... So intimate perhaps, that to an outsider, it almost seems as though you are the singular tourist on the beach.

As other traditional communities have grown in notoriety, this summer colony remains quaint, private and exclusive. The New York Times notes that "Watch Hill impresses visitors with a strong sense of discreetly used wealth—the rambling, old-fashioned, turreted and gingerbreaded Victorian summer houses with piazzas and softly rolling lawns have little in common with the overpowering castles of the very rich in Newport, a place rarely mentioned in Watch Hill even though it is barely 30 miles distant."

Watch Hill is located in Westerly, Rhode Island with a population of less than two hundred, and just two hotels - the Ocean House and the Watch Hill Inn. Both are historic sites, managed by the Ohm Collection and are in walking distance from one another. The Ocean House is New England opulence from floor to ceiling. It is the only Forbes Five-Star and AAA Five Diamond Hotel in Rhode Island, and only one of eleven triple five-star resorts,world wide. It's chic,minimalistic sister property, the Watch Hill Inn, has only twenty-one rooms and is brimming with historic charm. Both overlook the water and bluffs, and offer renown onsite dining.

Pictured off to the distance, the large, saltbox house behind Kennedy is owned by Taylor Swift - and the chain link fence guards her perimeter from the public beach (surprisingly, her driveway is adjacent to the public entrance). Known for Taylor's star-studded Fourth of July parties; the singer recently released a song about the home, its hosts, and all wild happenings that have occurred within its walls, entitled "The Last Great American Dynasty."

Distance from Local Attractions:

Watch Hill Beach: .1 miles

Atlantic Beach Park: 4 miles

Frosty Drew Nature and Observatory: 10 miles

Babcock-Smith House: 5 miles

Mystic Seaport: 16 miles

Narragansett Towers: 25 miles

Old Lighthouse Museum: 11 miles

Suggested Minimum Length of Stay: One night

Top Value: Winnapaug Inn

Top Moderate: Watch Hill Inn

Top High: The Ocean House

Top Bonvoy: Mystic Marriot


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