Tucked inside the quaint town of Westerly, Rhode Island is a charming coastal village spanning less than one square mile. Despite its small size, the village boasts plenty to offer, so much that its stunning landscape, history, delicious eats, historic architecture proved powerful enough to lure in billionaires like Taylor Swift and celebrities like Conan O’Brien—who’s set to host the Oscars, this weekend.
While locking in a permanent residence in this zip code comes with a high price tag, Amtrak tickets are as cheap as $8. Even if you’re on a budget, you can enjoy all the beauty this village, just 90 minutes from Boston, has to offer.
Traveling from Boston to Watch Hill, Rhode Island
Even carless, it’s easy to access some of New England’s coastal towns aboard the Amtrak Northeast Regional, such as the charming villages of Watch Hill and neighboring Mystic.
The train departs South Station several times a day, on the daily, and delivers you straight to the heart of Downtown Westerly, a larger town of which the village of Watch Hill coinhabits. A quick 7 minute car share, 20 minute bike, or car rental from Westerly takes you to the start of Watch Hill Road that travels all the way to the tip of the village, filled with several attractions..
Things to do in Watch Hill, Rhode Island
Taylor Swift brough plenty of media attention to Watch Hill when she purchased the former home of socialite, philanthropist and entrepreneur, Rebekah Harkness. Her song, “The Last Great American Dynasty” chronicles the story of Harkness and transition of the home ownership.
While the home is not accessible for obvious reasons, its large presence is impossible to miss when exploring nearby attractions, namely, East Beach and Watch Hill Lighthouse.
The sight for the lighthouse served as a beacon for incoming sailors since 1745, the town converted the structure from wood to granite in the 1800s.
Taylor’s “Holiday Home” is sandwiched between East Beach and the lighthouse, so Swifties will enjoy a peak of the facade. East Beach gains attention as one of New England’s most beautiful beaches, with gorgeous sands, clear waters, surf, and beautiful sunsets.
In Downtown Watch Hill you’ll encounter a plethora of dining and shopping options. Adjacent to the shops is a national landmark, the nation’s oldest continuously operating flying horse carousel. The merry-go-round dates back to 1867 and still offers rides to this day. It’s cited to create a unique “flying” sensation for those who ride.
Under 1 square mile and just over 500 acres, the entire village is on the smaller side, making it easy to explore the whole thing in one trip. But it’s so pretty, you’ll easily want to extend your stay!
Where to stay in Watch Hill
There’s really only one place to stay in Watch Hill: Ocean House. This notorious yellow estate, built in 1868, ranked among the world’s best waterfront hotels. Praised for its picturesque bay-view windows, over 5 concepts serving world-class cuisine , racquet sports, yachting, biking, on-site surf house, and events, Ocean House is reason enough to visit Watch Hill. The resort is one of New England’s most coveted stays. Guests also enjoy private beach access and cabanas with oceanside dining.
Despite owning a house next door, Taylor Swift is rumored to wed Travis Kelce at Ocean House this summer.
The golden stay isn’t without a price tag. Those seeking a budget-friendly alternative can explore local vacation rentals or a local inn. Bordered with Mystic, Connecticut, the neighboring Connecticut Village offers even more lodging options and is just a short distance from Watch Hill.
