Downtown Westerly, Rhode Island

Though Westerly is known for its abundance of shorelines, the beaches are just the beginning. Rhode Island’s southernmost town is also home to a thriving downtown scene brimming with local shops and trendy bars and restaurants. (Not to mention, a pop star with a certain ‘reputation’ was so enchanted by the area that she now calls it home.)

SHOP: A good book and a cup o’ Joe from Savoy Bookshop and Cafe; a beachy bracelet from the Compass Rose; some wall art from the Eagle’s Nest Gallery; a box of quality truffles from Hauser Chocolatier (closed Sundays); a pretty sundress from Christina’s Ltd.; the perfect pair of jeans from Woodmansee’s Gifts and Boutique and some all-natural skincare products from Herbwise Naturals. For more ways to shop like a local, check out ShopLocalRhodeIsland.com. 

EAT: Some cream puffs from Vesta Bakery; truffled eggs at the Cooked Goose; a hot and dirty martini at Perks and Corks; a Cabo San Lucas Taco at Amigos Taqueria y Tequila; a glass of Watch Hill White Wine at the Tapped Apple Cider and Winery (open Friday, Saturday and Sunday); or cherrystone clams from the raw bar at Bridge Restaurant.

DO: Wilcox Park features a beautiful landscape defined by an open meadow area with surrounding trees, a fish pond, monuments, and perennial gardens or visit Napatree Point Conservation Area for a hike. Finish off your fun-filled day by grabbing a carload of friends and family and enjoy an outdoor movie at the Misquamicut Drive-In (May-October). 

STAY: Your choice of accommodations in the area runs from high-end luxury, to eclectic, historic, and cozy. For world-class luxury, you can't beat Ocean House - one of only thirteen resorts in the world with a triple 5-star rating. Perched high on the bluffs of Watch Hill, boasting its own private beach and spa (and famous pop-star neighbor) the Ocean House hosts a variety of events year-round and classes at its Center for Wine and Culinary Arts. Ocean House's sister property, Weekapaug Inn sits on the shore overlooking Quonochontaug Pond is known for cozy luxury and nature-based programming.  Shelter Harbor Inn provides upscale amenities in a country-esque retreat by the shore, celebrating the best of New England beauty and traditions. Or enjoy classic contemporary beach-side accommodations in the heart of Misquamicut Beach at Hotel Maria (closed mid-September to the end of April). Margin Street Inn offers low-key casual elegance on the banks of the Pawcatuck River.