‘Cast Away, Dropping Anchor in: Westerly/Watch Hill, Rhode Island

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By Laura Winters, Hilary Jenison & Ally Donnelly

Often people are looking for destinations within a short drive of #02043, and a quick search of social media boards reveals a list of the usual, albeit lovely, destinations. We got together with Ally Donnelly from The Hingham 'Cast and decided we wanted to check out a few lesser-known destinations to add to the list of must-see places to visit close to home. Thus, our new travel series “‘Cast Away: Dropping Anchor In ?” was born. For our first adventure, we set off for Westerly, Rhode Island, and Watch Hill's historic district.  

Join us as we take you through our adventure below and listen to this week's episode of The Hingham 'Cast to hear firsthand encounters and interviews with people we met along the way.  We'll share tips for where to stay, what to eat and things to do in the area as well as insider tips from locals! 

Disclaimer: We received no compensation from the places we visited and the reviews are based on our experiences. 

We departed from Hingham at approximately 10 am, and after a quick and easy 1.5-hour drive, we arrived at the stunning Margin Street Inn.

Where to Stay in Westerly/Watch Hill

Though Watch Hill is known for the famous Ocean House Resort, we decided to act on the advice of a Hingham local who hails from Watch Hill and stay at the equally luxurious but more approachable Margin Street Inn. The Inn is located between the village of Watch Hill and Downtown Westerly.

The Inn is perched on the banks of The Pawcatuck River in Downtown Westerly and features lovely manicured grounds and an 1849 complex of homes. In addition to the exquisite Colonial and Classic Revival style guest houses, the grounds, views, and stunning giant Beech trees made for a dramatic entrance.

Once inside, we met the proprietors of the Margin Street Inn, Sarah and Chris Cooper. They offered the warmest welcome and promptly showed us to our beautifully appointed rooms in the thoughtfully restored and renovated property.

In advance of our arrival, we booked three rooms in the Beech House, which is the guest house just across the lawn from the Main House. Our rooms were beautifully and impeccably decorated, and each offered a distinct color palette, theme and experience. Some rooms are even appointed with in-room fireplaces, and many offer riverfront views. It is a serene setting and tranquil retreat, which is why guests at the Inn must be 14 years of age and above.

In each of the Inn's 10 guest rooms, no detail was overlooked to provide the most luxurious guest experience including Matouk and Ralph Lauren linens, Pogessi bath products and spectacular works of original art. It is a wallpaper lovers paradise!

Downstairs living areas in both the Main House and the Beech House feature multiple sitting areas, dining areas, cozy fireplaces and refrigerators stocked with guest favorites such as water, wine, beer and soft drinks. We were the only guests staying in the Beech house that evening, so it truly felt like our very own home away from home.

At 5 pm each day, Sarah and Chris host a happy hour for guests to meet and mingle before heading off their separate ways for dinner and evening activities. As was the case with the rest of our stay, this gathering hour did not disappoint. We learned more about the Inn and the area's history, met another traveler (a renowned author) and enjoyed delicious Rose and charcuterie.

After a good night's sleep, Sarah and Chris introduced our group to the pièce de résistance of the Inn; the breakfast spread.

It was clear that Sarah and Chris had been up for hours creating the masterpiece that was the breakfast bar, which is complimentary to Inn guests. Several of our favorite items included homemade mushroom frittata, an avocado toast buffet, homemade granola, freshly-baked muffins, and bacon. We enjoyed every bite of our long, leisurely breakfast while chatting with our hosts.


Sarah and Chris treated us to a tour of the grounds and the newly renovated out building that will now serve as an event space. These two are delightful and warm and are truly the heart of the Margin Street Inn. They love what they do and it shows in every detail of the guest experience. From the bespoke guest rooms and interior decor to the food to a relaxing stroll of the grounds, the Margin Street Inn will impress even the most discerning traveler. We are looking forward to returning very soon!

What To Do and Where to Eat in Watch Hill Rhode Island

After getting settled at the Inn, it was time for us to start exploring the area! The Margin Street Inn is about a 10-minute drive to the quaint historic district of Watch Hill and walking distance to the center of town in Westerly, RI. Our original plan was to hit the beach for the afternoon; however, the weather did not cooperate. Locals told us that it’s often cloudy and foggy in Watch Hill, but it usually burns off by early afternoon, so it’s wise to check the forecast. Regardless, there is plenty to do in Watch Hill with or without sunshine.

We opted to have lunch at Ocean House, the grand dame resort of Watch Hill. Ocean House sits atop Watch Hill, overlooking both the ocean and the village below. With her gorgeous yellow Victorian architecture and her sweeping veranda views – Ocean House is not to be missed. While the price tag is expensive to stay overnight (and for good reason), it’s a must-see for lunch, dinner, or drinks on the veranda, even if you are not staying there. We hear that Al, the resort piano player, is a local gem. Unfortunately, Al was out of town during our visit, but we have it on good authority that he plays by the lobby bar at Ocean House on weekend nights and is a hit with guests and locals alike.

Holiday House (Now Known As Taylor Swift’s House)  

After lunch, we set out to explore and do what many visitors to the area do – find Taylor Swift’s House! The woman in the shop at Ocean House told us to take a left out of the Inn and that we couldn’t miss Taylor’s house “it’s the white house, the GIANT one.” Welp, she was right. A quick walk down gorgeous Bluff Ave, and you can’t miss the private gates of Holiday House, now better known as the Swift Residence. We were told that Taylor and her family were there during our visit (evidenced by the increased security at the house with the pacing, armed security guards inside the gates); however, we did not catch a glimpse! Rumor had it, Bill Clinton was also visiting, but we digress …

Holiday House was built in 1930 for the Harkness family, heirs to Standard Oil, and Taylor Swift purchased the home in 2013. Rebekah Harkness, the founder of Harkness Ballet, lived in Holiday House and was well known in her day for her eccentricities, infamous antics, lavish parties, generous contributions to the arts, and her very own female squad known as the "Bitch Pack."

Swift details the life of Rebekah Harkness and draws parallels to her own life at Holiday House in the song “The Last Great American Dynasty” on her Folklore album.

East Beach

It was somewhat surprising how public the location of Taylor Swift’s home is at her level of stardom – it is directly adjacent to the public beach entrance of East Beach. A quick walk down the public stone pathway, and you enter one of the most beautiful beaches on the Eastern seaboard with massive surf waves, beautiful views of the Watch Hill Lighthouse, Ocean House Resort, and clear view of the Swift Residence above.

While parking is not entirely convenient for East Beach, it is a quick walk from Ocean House and Watch Hill, and it's free to enter. There are no dogs allowed on the beach from May-Labor Day. We also heard from a few locals that Napatree Beach is worth visiting and that Carousel Beach is the spot to go for families (with lifeguards, lockers, and a public restroom).

Exploring & Shopping in Historic Watch Hill Village

We left East Beach and continued on a one-minute walk down Larkin Rd., passing a walking path out to the lighthouse and right into the historic district of Watch Hill. We immediately came to the Flying Horse Carousel, the oldest operating carousel in the U.S. The Carousel is certainly a highlight for kids and families visiting the area, but we decided to forego a ride and get to some shopping! 

Watch Hill's historic district is full of many adorable shops and eateries, a great way to spend a day. We meandered into many shops ranging from beach attire and Watch Hill gifts/ memorabilia to high-end home décor and clothing boutiques. A few not-to-be-missed shops include Coppola’s BoutiqueThree IslandsCoco & LalaHighpoint Home, which reminded us of Hingham’s Doublemint Home, and so many more!

Dining in Watch Hill

With the exception of Ocean House, eating in Watch Hill is a pretty casual affair. Ocean House provides a high-end experience and requires no beach attire and jackets for gentlemen in the public areas. Lunch in the Bistro was delicious, and we were able to share the signature Ocean House Bistro Salad, chowder, and the new Thai steak lettuce cups were delicious!

In the afternoon, we stopped by St. Clair Annex to meet owner James Nicholas and his father and taste some ice cream. St. Clair’s has been a family-owned and operated ice cream and sandwich shop located in downtown historic Watch Hill since 1887. Listen to The Hingham 'Cast for our full interview with James on the history of his family’s shop, including his favorite ice cream flavors! Insider tip, you can always tell the best ice cream shops by the flavor of their vanilla, and St. Clair’s does not disappoint (we also heard the cantaloupe is to die for, but sadly it was not in season).

For dinner, we opted to visit the Olympia Tea Room based on numerous local recommendations. There are no reservations at Olympia, and there was about a 45-minute wait, but that was not a problem because it gave us another excuse to head up the hill to Ocean House and grab a cocktail on the veranda to take in the sunset – a highlight of the trip!

A call from the restaurant indicated our table was ready, and with a quick golf cart ride, we arrived at The Olympia Tea room in minutes. The Olympia Tea Room is a family-owned bistro, often referenced as the “heart beat” of Watch Hill, with both indoor and outdoor dining. The nostalgic restaurant was buzzing with energy on a foggy Monday, so we can only imagine the weekend vibe!

The food at Olympia Tea Room was fabulous! We started with a few appetizers based on recommendations, including the Crisp Zucchini Ribbons, a Burrata Salad special, and the Tuna Sashimi. We finished by sharing the Crispy Chicken (again a local favorite). Everything was delicious, but the zucchini ribbons were the favorite!

Watch Hill does not have a vibrant nightlife which adds to its charm. After our late dinner, the town was nearly asleep, and we were ready to head back to the Margin Street Inn. The perfect evening for three tired mom’s on the loose!

Downtown Westerly, Rhode Island

The following day after our delicious breakfast (see review above!), we explored the Downtown area of Westerly before heading back to Hingham.

The town of Westerly is walking distance from The Margin Street Inn, but we opted for the few-minute drive given our timeline. We stopped by the Savoy Bookshop, an independent book store exploding with charm (and great coffee)! Anna Skinner Garceau, a Savoy Book store employee, just happened to have grown up in Hingham, proving that all roads DO lead back to the #02043. Anna tipped us off that next time we visit Westerly, we HAVE to check out Westerly Meat Packing and try their world-famous SOUPY!

Before heading home, we checked out the gorgeous Wilcox Park, and we’re so glad we did. It is a beautiful park designed by Warren H. Manning, a former associate of Frederick Law Olmsted who was also known for designing Central Park and the founding father of the American Society of Landscape Architects (ASLA).

Watch Hill Review

In summary, Westerly and its historic district of Watch Hill is as charming as it gets and is not to be missed! In less than two hours, you can be in this picturesque Rhode Island gem without the hustle and bustle of Newport. Watch Hill is a community with a strong connection of locals who are like one giant family proud of their seaside oasis and welcoming to guests. Definitely check out the spots above, and if you go, don’t forget to tell them that the ladies from the Anchor and The Hingham 'Cast sent you!

This feature was brought to you by our awesome sponsors - Orange Theory Fitness Hingham and Doublemint Home.

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