If I could live anywhere in New England, I’d pick Westerly. You’ve got a great downtown packed with quality restaurants (many from owners who’ve migrated from New York City), great access to beaches, and you’re only a couple of hours from both Manhattan and Boston.
Check In
If you don’t balk at spending $2k/night, book a room at Ocean House, the iconic yellow hotel on the water in the scenic Westerly neighborhood of Watch Hill. And yes, it’s next to the Taylor Swift house.
Other more economical options include the Watch Hill Inn right down the street from Ocean House or the Margin Street Inn in downtown Westerly.
Eat Like It’s an Olympic Sport
Cinder: Perched on the Connecticut River that divides Westerly, Rhode Island from Pawcatuck, Connecticut, Cinder is my fav Westerly spot to sit outside with margaritas and tacos.
B&B Dockside: A great brunch spot with outdoor seating and marina views.
High Hope Tavern: A downtown Westerly spot with a cool bar scene.
Nana’s: Homemade breads, pastries & pizza dough are the standouts at this all-day cafe.
The Cafe: Creative food and a fun, upscale vibe.
Drink Like a Local
Perks & Corks: Home to (what I think is) the world’s largest martini. Some are so big they only allow you to order one. Nights that begin, end or involve a trip to P&C usually end in blackouts, aka ‘getting perk’d.’
Grey Sail: Brewery in a historic home with a ton of outdoor space.
Ocean House: While I’ve never stayed over, I’ve been to this beachfront hotel (that sits next to Taylor’s house in Watch Hill) a couple of times and each time has been iconic. Whether it’s for a martini at the lobby bar or a summer lobster bake on the beach, Ocean House is worth a visit.
Where to Caffeinate
Junk ‘n Java: Coffee, espresso drinks and smoothies.
Stalk the Stylish Locals
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An aesthetic take on all things Rhode Island.
Excursion-Worthy
For my sister’s 40th bday, we did a scavenger hunt around Westerly so I can tell you all the weird things to see (Florence Nightengale’s cap at the Westerly Hospital, a giant Mr. Potato Head at the airport), but I’ll spare you and only share the worthy ones.
Mystic, Connecticut: A scenic former whaling village on the water with great restaurants & bars.
Block Island: Take a ferry from Point Judith or Newport, or a heli ride from Westerly to spend the day or a weekend.
Watch Hill: Home to Taylor Swift’s beach house, this tony Westerly neighborhood is packed with beautiful beaches and real estate porn.
Misquamicut: The yin to Watch Hill’s yang, this beachy Westerly neighborhood is where you go to see Pauly D guest DJ a set and Kyle from Summer House do a Loverboy promo. Both at Paddy’s Beach Club, of course.
Stonington Vineyards: Bring your pup and a picnic to enjoy on the vineyard grounds.
Mohegan Sun: Only 30 mins away, this casino hosts a number of concerts throughout the year, including major acts doing arena shows and one-hit wonders that perform for free on the casino floor.
Saltwater Farm Vineyard: Another scenic vineyard about 10 mins from Westerly.
