Watch Hill is an affluent community on Westerly’s southwest corner overlooking Block Island Sound. Anyone who has ever visited this village knows it provides a one-of-a-kind vacation experience you won’t soon forget.
From the second you arrive in Watch Hill, you’ll be blown away by the architecture. The reason is that most homes would be considered mansions, and some of them are absolutely breathtaking.
You’ll feel like you’re in rare company when booking a vacation rental in Watch Hill, and you’d be right because the community only has 141 full-time residents.
Despite the village’s small size, you’ll never run out of things to do on your holiday. Here’s a look at some ways you can spend your time while vacationing in Watch Hill.
Go to the Beach
When visiting Watch Hill in the summer, a stop at the beach is almost certainly in order. Fortunately, the village has multiple options, depending on the location of your vacation rental and your personal preferences.
Watch Hill Beach is your best bet if you want first-class amenities. It sits in downtown Watch Hill, where Larkin Road and Bay Street meet, so it’s close to dozens of dining and shopping options. It’s also the only beach in Watch Hill with nearby parking.
It’ll cost you $10 per adult and $5 per child to access Watch Hill Beach, and seasonal passes are available. This beach is also home to the iconic Watch Hill Merry-Go-Round.
For a more rustic oceanfront experience, East Beach is worth checking out. This long expanse of sand extends all the way to Maschaug Pond and is lined by some of the most impressive mansions you’ll see in the village, including Taylor Swift’s summer home.
You can access East Beach in numerous spots, such as Bluff Avenue, Everett Avenue, Niantic Avenue, and Manatuck Avenue, but keep in mind that none of these streets have parking, and some don’t permit drop-offs. As a result, your best bet is to walk to the beach from your vacation rental.
Finally, you can hit the beaches in the Napatree Point Conservation Area. This park sits just west of downtown Watch Hill and features hiking trails that will take you out to the ruins of Fort Mansfield, a former Army base.
You can venture off the trail, down the dunes, and to the water wherever you wish, or walk along the beach to Napatree Point. Either way, soft sand and scenic views are waiting for you.
Visit Some Restaurants
The dining scene in Watch Hill is noteworthy because of its quality, although the village doesn’t have many options.
St. Clair Annex is a popular breakfast spot right by the beach that also serves lunch and homemade ice cream.
Ten Sandwiches sits just up the street and features a morning menu with breakfast sandwiches, coffee, and smoothies and a nighttime menu with pizza, oysters, and snacks. It also has a full bar.
Watch Hill’s best-known eatery is the Olympia Tea Room, a local staple that’s been open for over 100 years. The menu includes seafood favorites like haddock, tuna, oysters, lobster rolls, clams, and shrimp, although you can also order cheeseburgers, pizza, spaghetti, steak, and chicken.
Of course, your vacation rental will also have a kitchen, so you don’t have to rely on local restaurants the entire time.
Check Out the Boutiques
Watch Hill has an upscale feel, and the village’s boutique retailers add to this atmosphere.
Local favorites include Coppola’s, Gabrielle’s Originals, Seaport Studios, and Rochelle’s, all of which offer the latest styles. Tami-Anns, JC’s of Watch Hill, Breezy’s, WH20, Three Islands, and Coco and Lala are also worth exploring.
Mama’s Gardens Skin Care and Lolo are top choices for cosmetics or beauty products, while Perfect Pineapple and Christina Stankard sell jewelry.
All of these shops sit within a two-block stretch of Bay Street, so you can spend the entire day exploring Watch Hill without having to travel far.
Your Watch Hill Vacation
Your vacation to Watch Hill can take many different forms, as you can hit the beach, visit some retailer, explore the dining scene, or relax at your vacation rental. This community is also a short distance from the lively village of Misquamicut, which is home to Misquamicut State Beach, Atlantic Beach Park, and some oceanfront bars and restaurants.
Downtown Westerly and Charlestown are also easily accessible from Watch Hill, and you can even take the Pawcatuck River Bridge into Connecticut by driving north for about ten minutes.
Because parking is so scarce in the community, booking a vacation rental in Watch Hill is advisable if you wish to use the village’s amenities during your time in South County. And not to worry, as the rest of this beautiful region is easily accessible from this amazing neighborhood.