It has a long and storied history, but chances are you may not have heard of Watch Hill until Taylor Swift put the Rhode Island town on the social media map. Her once-celebrated, now discontinued annual 4th of July party was extensively documented on Instagram and in the celebrity press, and suddenly, the picturesque town was introduced to America (via Instagram, of course) as the playground of the young, the blonde, and the insanely wealthy.

But Watch Hill doesn’t exactly pride itself on ostentatious displays of celebrity. And as Swift has adopted a lower profile these past few years, this Ocean State oasis has returned to its understated roots. It’s a tribute to the town’s resilience that it has remained so under-the-radar, and with that in mind, we’re casting the spotlight on Watch Hill for this edition of carless weekend getaways. Read on to find out why this southern Rhode Island spot should be on your New England travel bucket list.

Watch Hill coastline, Westerly, Rhode Island, USA.


You’ll start your trip by hopping on a Westerly-bound Amtrak train or a Providence-bound bus from New York or Boston, then taking a cab to your final destination once you’ve arrived at the station. Since Swift’s mansion, High Watch, is strictly off-limits, may we suggest some just-as-posh digs? A spot that even has a cricket lawn — not to mention room service. We’re talking, of course, about the Ocean House, the iconic hotel where guests are encouraged to live like characters in a Gatsby novel.

If the luxe Ocean House is a little out of your price range, we suggest the less-spendy Weekapaug Inn, which is run by the same owners. Or consult Airbnb, VRBO, and HomeAway to see if you can rent a cottage with friends for some of the most cost-efficient (not to mention picturesque) lodging available.


Unlike the bustling communities of previous destinations such as Montauk or Martha’s Vineyard (and the attendant endless waits for a dinner reservation), the pace in Watch Hill is decidedly slower. While the town offers relatively little in the way of nightlife or restaurants, it’s precisely that quaintness that gives it much of its appeal.

The Ocean House is the hub for much of the town’s social activity, and luxury-seekers should reserve one of the resort’s striped cabanas (and order a bottle of rosé) and pretend they’re in St. Tropez for the afternoon. The sight of waiters walking up and down the sandy beach delivering glasses of Champagne certainly feels more South of France than New England, and the rows of yellow lounge chairs facing the sea give off the blissful ambiance of a Gray Malin photograph.

Further down the coastline, East Beach is another destination for swimming and lounging. Visitors interested in bird-watching should check out the rugged beauty of Napatree Point Beach. The 1.5-mile walk to the end of the sandy peninsula is a journey through untouched nature that snakes out toward Little Narragansett Bay. History buffs will appreciate the Civil War ruins of Fort Mansfeld on Napatree Point. And if ruins aren’t your thing, visit the Flying Horse Carousel, the oldest in the country, dating back to 1876.

The walk to the Watch Hill Lighthouse is another picturesque excursion, as is renting a kayak from Watch Hill Outfitters to explore the rivers and ocean of Southwest Rhode Island. If you’re interested in an aerial perspective, HeliBlock Helicopter Tours offers excursions from the Westerly Airport to nearby locales like Fishers Island. If you’re feeling extra brave, you can elect to fly with the doors off.

Rainy days indoors call for coffee at Savoy Bookshop (once a former movie theater) and a visit to The United Theater in Westerly (which recently underwent an elaborate renovation).


Start your morning with a cold brew from Dave’s Coffee in nearby Charlestown or, if your previous night out requires some heartier sustenance, head over to St. Clair Annex (just remember, it’s cash only).

The Cooked Goose is a slightly more upscale option for breakfast and lunch, with delicious prepared foods as well as famously tasty breakfast sandwiches. You should expect a 45-minute wait on Saturday and Sunday mornings if you don’t wake up early, so if you’ve gotta have one, set an alarm.

Pick up sandwiches, salads, and Dells Frozen Lemonade (a Rhode Island specialty) at Ten Sandwiches before heading to the beach. This is a good spot for grabbing beer or wine as well.

Spend the afternoon at Matunuck Oyster Bar to enjoy great food, great views, and great shellfish in a beautiful place spot overlooking the water. If you’re up for a short (25 minutes or so) drive, check out the $5 happy hour on Tuesday through Friday at Bravo Bravo in Mystic, Connecticut (and, if you love Julia Roberts rom-coms, Mystic Pizza, as well).

For the best cloudy day activity of all, sign up for a tour and wine tasting at Langworthy Farm. Or head to Grey Sail Brewing in Westerly to learn all about the beer brewing process. Pick your poison and prepare to while away your afternoon in the most perfect (and educational) way possible.

The Olympia Tea Room is a must-visit for dinner. At this Watch Hill restaurant, the decor is as eclectic as the menu. Artwork painted by the owner’s wife adorns the bright pink walls, and the food is truly excellent. Order gin martinis before your meal, and celebrate with the restaurant’s signature dessert, the Avondale Swan: ice cream on a puff pastry with whipped cream feathers. Trust us, it’s delicious.

But why stop there? Return to the scene of the (breakfast) crime and walk to St. Clair Annex after dinner for the best ice cream on the East Coast.

What are your favorite beach towns in Rhode Island? Tag us in your go-to spots on Instagram @BritandCo.

(Photos via Getty)

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