Watch Hill: A Complete Guide

The exclusive-feeling seaside community of Watch Hill—one of five villages in the town of Westerly, Rhode Island—has retained its Victorian charm while asserting its place among New England's finest modern-day resort destinations. Music superstar Taylor Swift, who famously calls Watch Hill's Holiday House one of her many homes, has attracted attention to this secluded coastal village in the South County region just by her rare presence. But it is luminary investment manager Chuck Royce who has done the most to raise Watch Hill's profile. The passion and money he has poured into restoring hotel properties here—most notably the AAA Five-Diamond and Forbes Five-Star rated Ocean House—has made Watch Hill the place for elite vacationers and those who love the idea of spending a day or more in their midst.

Walk along soft-sand beaches, shop in boutiques, sip cocktails, feast on seafood, and watch the sunset and the lighthouse beam—however you plan your trip, you're in for a luxurious getaway.

Things to Do

First and foremost, Watch Hill is a beach town, with several options for swimming, sunbathing, sandcastle building, strolling, and savoring salty breezes. Gentle surf isn't the only reason the village appeals to families with children. A historic carousel—just for small riders—is the stuff of childhood memories. Saltwater sportfishing attracts visitors, too. And remember: You're at the gateway to the smallest state in the union, so Rhode Island's many other attractions are a short drive away.

While in Watch Hill, you'll want to:

• Spend Time at a Beach: There are three publicly accessible beaches to choose from in Watch Hill. Although Watch Hill Merry-Go-Round & Beach is small, often packed, and has an admission fee, the family-friendly spot is within walking distance of everything and features restroom facilities. East Beach is difficult to access and has no amenities, but it is clean, quiet, and picturesque. For surfers, it also boasts more vigorous, grown-up waves. Napatree Point Conservation Area is the most storied of Watch Hill's beaches. A curved tendril of sand, this barrier beach's homes were destroyed when the Great New England Hurricane of 1938 made landfall with little warning. Now, this "ghost town" of a beach is a contemplative place to walk, fish, birdwatch, bask in the sun, picnic, take photos, and watch sunsets.
• Treat Kids to the Carousel Ride of Their Lives: Only kids under age 12 can ride America's oldest surviving Flying Horse Carousel, with its horses suspended from chains and brass ring game (grasping one earns the rider another round on the carousel). Even though adults can't ride, you'll appreciate the artisanship of this mid-1860s classic, abandoned in Watch Hill by a traveling carnival in 1879. Each antique carousel horse was carved from a single piece of wood. Saddles are made of leather, while the tails and manes are crafted with real horsehair. The carousel operates during the summer season only.
• Visit the Watch Hill Lighthouse: Built of granite in 1856, the Watch Hill Lighthouse is a sight to see year-round. It's visible from Watch Hill Merry-Go-Round & Beach, and you can also walk down private Larkin Road to view and photograph the lighthouse up-close any day between 8 a.m. and sunset. From July 1 through the week after Labor Day, its museum is open on Tuesday, Wednesday, and Thursday afternoons from 1-3 p.m.

Explore more of the Ocean State with our guides to Rhode Island's best beaches and the best things to do in Rhode Island.

What to Eat and Drink

From basic beach eats to superb dining with an ocean view, you'll find Watch Hill fulfills diverse cravings. This is the Ocean State, and seafood is on many visitors' minds, but it's also the sort of place where allowing your kids to eat ice cream for lunch is just fine. St. Clair Annex, owned by the Nicholas family since 1887, is an affordable place to feed your crew breakfast, sandwiches, or old-timey ice cream fountain favorites like banana splits and root beer floats. The “famous not fancy” Olympia Tea Room, open seasonally, has a similarly long, century-plus history of serving up a classic, bistro-style menu. When you do want fancy, book one of Ocean House's sumptuous dining experiences. In addition to its on-site fine dining restaurant Coast, the hotel offers three outdoor dining options in the summertime including the Verandah Raw Bar. In the winter, you also have a fun opportunity to dine in the Gondola Village.

Where to Stay

The Ocean House grand hotel is perched on a hilltop, with the ocean and the village of Watch Hill below. Built in 1868, the luxury property deteriorated until it was finally shuttered in 2003. Bringing this Victorian gem back to life in 2010 required a painstaking rebuild, using many salvaged architectural features. It is a rare place that feels at once old and new, and it's a must-visit even if affording a night's stay is out of your reach. For a fraction of the cost, you can stay at the 12-room Watch Hill Harbour House in-season, but be aware that a two- or even three-night minimum stay may be required. Parking is included: a real perk in this town. Airbnb and VRBO both have listings in Watch Hill, and the Ocean House-managed Watch Hill Inn is lovely, too. For a B&B or chain hotel, you'll have to stay in another part of Westerly or across the Connecticut state line in Stonington or Mystic.

Best Time to Visit

Watch Hill's allure is at its peak during the summer season, from Memorial Day weekend through Labor Day weekend. Of course, summer is crowded, too, and parking can be hard to come by in this little village if you don't arrive early in the day. If the weather is warm, a visit during the shoulder seasons—early May or September through early October—can be ideal. In the wintertime, many shops and restaurants shut down, but Ocean House remains a destination for dining and overnight stays by the frosty shore. Plus, a walk on the beach during the winter months can be a tonic for the soul if you bundle up properly.

Getting There

Watch Hill is surrounded on three sides by water, and there is really only one way to get there: in a vehicle, driving toward this point of land on Route 1A from the east or west. You can get close to Watch Hill by flying to Westerly State Airport via a private or chartered plane, a Wings Air helicopter, or a New England Airlines scheduled flight from Block Island. However, you will still need to rent a car or summon a taxi or Uber. T.F. Green International Airport in Warwick, Rhode Island, is the nearest major airport. The closest train station is in Westerly and is served by Amtrak. RIPTA buses also deliver passengers to the Westerly railroad station.

Money-Saving Tips

• There is free parking in Watch Hill on Bay Street, near shops and restaurants, but available spots are claimed quickly.
• For retail therapy on a budget, visit some of Watch Hill's more affordable shops like Rochelle’s Boutique, Three Islands, Bay Breeze Interiors, and the Watch Hill General Store.
• When kids beg to ride on the Flying Horse Carousel, you can relent knowing it's just $1 to ride on an inside horse or $2 to gallop along the outside for a chance to grab the brass ring and earn a free ride.
• For an experience of Watch Hill on the cheap, pick up a light meal at Ten Sandwiches, then enjoy a hike and picnic on Napatree Point. Walk all the way to the end, then take one of the trails heading away from the shore, and you may stumble upon the ruins of Fort Mansfield.
• Walking onto the beach here is absolutely free!