Travel with a Local: Westerly, Rhode Island

Why should we visit your town/city?

There are only two places in the world named Westerly, and this is the one to see. Westerly, Rhode Island is—as my father would say—nothing short of paradise: “I’ve lived in Westerly for more than thirty years and I still haven’t gotten over it.” From the burgeoning historic downtown to the coastal villages of Watch Hill and Weekapaug, there is much to discover in this quintessentially New England small town.

While perhaps best known for its beaches, Westerly still makes waves miles inland. Inside the westernmost town in Rhode Island one can find art and antiques aplenty. Outside, one can easily access the Atlantic Ocean from Westerly’s many beaches or kayak down the Pawcatuck River, which marks the boundary between Rhode Island and Connecticut. If you prefer to walk or hike, there are plenty of parks and trails around town.

One of the most attractive assets of Westerly is the ease of traveling to and from by plane, train, automobile—or boat, for that matter! From the centrally-located train station you can catch a train northbound to Boston or southbound to New York or D.C. Westerly also has its own modest state airport, from which you can board a helicopter to Block Island. Or if sailing or ferrying is more your style, there are ports just down the road in South County or via New London, Connecticut.

Home to more than a dozen properties listed in the National Register of Historic Places, Westerly is replete with stories to tell. Be sure to see the Flying Horse Carousel—one of the oldest operating in the country—or swing into the Misquamicut Drive-In for a movie on the beach in the summer. For an indoor show, head downtown to the revitalized United Theatre, the Granite Theatre, the Knickerbocker, or see the Chorus of Westerly at Kent Hall—all located within a mile of each other! Be sure to leave time to take a shoreline walk to Napatree Point and the Watch Hill Lighthouse or a pit stop at the lookout in Weekapaug.

Where to stay?

The Ocean House is probably the most iconic stay in Westerly. This seaside resort is only one of fourteen in the world to be named a triple Forbes Five-Star property, with its fine dining and spa experiences also boasting five-star ratings. You’ll find it on the bluffs of East Beach in Watch Hill—a hop, skip, and jump from Taylor Swift’s infamous High House, which she bought back in 2013.

Other options include a series of idyllic inns, such as the Weekapaug Inn, Shelter Harbor Inn, and Margin Street Inn.

Where should we eat?

For breakfast or lunch, enjoy classic Irish cuisine at Kelley’s Deli, “get goosed” at the Cooked Goose, or browse a breakfast- and burger-centric menu along the Pawcatuck River at B & B Dockside. Seek out seafood down by the beach at Two Little Fish or Maria’s Seaside Cafe and you’re guaranteed to leave satisfied.

Indulge in gourmet pizzeria at Casa Della Luce, pies & subs at PizzaPlace in the heart of downtown Westerly, or homestyle Italian cuisine at Vetrano’s for hearty helpings. For brews only, seek out Grey Sail Brewing, or look for the seasonal Del’s lemonade truck in Dunn’s Corners for a true taste of Rhode Island in summer. Satisfy your sweet tooth with ice cream at St. Clair Annex (Watch Hill) or cross just over the border into Pawcatuck, Connecticut for Mel’s Downtown Creamery.

Which coffeehouses are the best and why (for coffee, for atmosphere, for both)?

Junk & Java offers an “eclectic blend of local friendship and espresso” and a slew of signature drinks for coffee aficionados and tea lovers alike. Downtown, discover the comfy coffeehouse lounge of Perks & Corks; order a coffee milk latte or legendary espresso martini.

Need something sweet? Hit up Knead Doughnuts along the way. The family-owned, French-focused Sift Bake Shop boasts some of the best baked goods to accompany a cappuccino. Although it is only open between Memorial Day and Labor Day in Watch Hill, you can find it open year-round in nearby Mystic or Niantic, Connecticut.

Though a beach town, Westerly is no town to coast through. Take your time to stroll seaside and through downtown. If you can swing it, visit in the summer, spring, or fall to attend some of the best events in Wilcox Park, like Summer Pops or Shakespeare in the Park. Come bask in optimal temperatures and revel in Rhode Island’s finest colors.

Whenever you arrive, Westerly awaits you!

Editor’s note: Travel with a Local gives the jet-setting (or road-tripping) woman inspiration for a quick weekend trip, or suggestions for when she’s just passing through a town for work. If you’d like to write about your town, review our Readers Write guidelines here.