Ever since a certain pop star helped put the quiet little Rhode Island summer enclave of Watch Hill on the map, it has “swiftly” risen up the nautical town charts. Nestled just between the borders of Connecticut and Rhode Island, the town of Watch Hill is the epitome of unpretentious sophistication – the main drag boasts a Lilly Pulitzer on one end, and a centuries old Merry Go Round on the other. With a gorgeous stretch of white sandy beaches, an iconic and historic hotel sitting high on a hill and a food scene to satisfy all the senses, this little town has become a big star in it’s own right. A stroll down the picturesque Bay Street offers a waterfront view that is quintessential New England.
Where to Shop
Browse the eclectic selection of local shops for coastal home decor and preppy staples such as Lilly Pulitzer and J.McLaughlin, but it’s Coco and Lala that features the most fun and true local color collection in their very instagramable storefront. A quick side note: one of our favorite Bay Street stores, Christinas LTD recently closed their Watch Hill location, but are still open just 5 miles down the road in Westerly. It’s definitely worth a stop on the way in or out of town!!
And no stroll down Bay Street is complete without a ride on the The Watch Hill Merry Go Round, which is said to be the only surviving flying horse carousel in the country and the oldest continuously operating carousel in the United States.
Where to Savor
When it’s time for lunch or dinner, you can keep things casual with burgers and seafood salads at the historic Olympia Tea Room or pop in to the fun and decorative Ten Sandwiches – a misnomer as they also serve delicious flatbreads and small plates. If you are looking for something a little more elegant, take a quick stroll up the hill to the Ocean House, where you can choose from 6 restaurants, each with their own unique menu and views of the Sound. Availability and seating can be an issue in the summer so plan ahead and make a reservation if you are on a schedule.
Indulge your sweet tooth with treats from the summer location of Sift Bakery, the popular Mystic, CT bakery and cafe from Adam Young, former head of pastry at the Ocean House and winner of the Food Network’s “Best Baker in America”. The macarons and the delicate and buttery croissants are worth a trip to either location. Get your ice cream fix at the the popular corner spot – St Claire Annex Ice Cream or go around the corner to pick out pounds of penny candies and treats at the always busy and bustling The Candy Box. You’ll leave any of these shops with a smile.
Where to Stay
Looming high above the town like a golden watchman is the luxurious and iconic Ocean House, a Relais and Châteaux property that dates back to the 1860s. A complete gut renovation in 2010 elevated the property to it’s current elegance; the resort boasts six restaurants, an indoor and outdoor pool, sauna, and a Forbes Five-Star award-winning spa. There is nothing quite like it on the East Coast. The first time I drove up to the property, it took my breath away; something that still happens every time I see it. The private beach is accessed by a gate so pretty you won’t mind not being able to get in. But the views and amenities do not come cheap; this is a splurge for sure, one that is sure to leave a mark on the memory as well as the wallet. But no fear; there are several other family friendly resorts located just minutes down the road in Misquamicut Beach, including Pleasant View Inn, The Hotel Maria and Breezeway Resort. All are located on or near the beach with private beach access.
Even if your trip doesn’t include an overnight stay, plan to stick around for sunset. While the town may not be as well known as it’s famous pop star resident, it certainly knows how to put it on it’s own spectacular show.