13 Incredible Things to Do in Westerly RI And Watch Hill

WHY GO: There are things to do in Westerly RI – and the town’s Watch Hill section – you’d be hard pressed to do anywhere else.

In the late 1800’s, vacationers came to the coastal town of Westerly RI for fresh sea air and to frolic on clean wide swaths of sand.

Now, as you climb the hill that overlooks Watch Hill RI harbor on one side and the Atlantic Ocean on the other, you can almost hear the joyous shouts of those Victorian era travelers as they hauled their steamer trunks to the portico of the yellow Ocean House.

This splendid resort, originally constructed in 1868, was renovated in the late ‘aughts as a stunning Relais and Chateaux hotel, and is considered one of the best in the United States.

Among discerning travelers, Watch Hill is best known for The Ocean House. Fans know, also, that Taylor Swift, purchased a mansion down the street.

Ocean House beach Taylor Swift House on hill Watch Hill RI

But there are other reasons to discover this section of coastal RI. These include a restaurant owned by a woman chef who took down Bobby Flay on “Beat Bobby Flay,” and one of the last remaining “Brass Ring” carousels in the country.

Discover all this and more on the following South County RI getaway.

Find so much more nearby – including a hippy enclave, a haunted inn – and winter surfing beaches in our Things To Do in Narragansett RI and Things to do in South County RI posts.

Or, check out other Romantic Getaways in RI here.

Things To Do in Westerly RI and Watch Hill in South County RI


Since Victorian times, summer visitors have been grabbing for the brass ring on this diminutive, but historic “flying horse” merry go round, built in 1883.

On the National Historic Register, the Flying Horse Carousel in Watch Hill RI (not to be confused with Flying Horses Carousel on Martha’s Vineyard MA) is the oldest operating carousel in the country with horses suspended from chains. Open daily in season till Labor Day. Weekends only until Columbus Day. Check website for times.

WALK: Napatree Point Conservation Area, Watch Hill Rhode Island

If you desire to get away from the crowds, head out on the spit of sand called Napatree Point Conservation Area– a Wildlife Preserve with no lifeguard, bathrooms or services. Despite (or quite possibly, because of) that, many fans believe Napatree Point is “the most beautiful beach on earth.”

VISIT: Watch Hill Lighthouse

Many lighthouse lovers consider a visit to the Watch Hill Lighthouse to be one of the best things to do in Westerly RI. That’s because this one, commissioned by Thomas Jefferson in 1806, is open to tourists at limited times – and actually features a museum.

BEACH IT: Westerly Shoreline Beaches

Watch Hill aka Carousel Beach is probably the tamest and most family-friendly. Both the half-mile long Misquamicut Beach and three mile long East Beach are extremely popular in the summer.


DO/TASTE: GreySail Brewing of Rhode Island, Westerly

After setting up shop in the repurposed Westerly Macaroni Mfg. building, and launching their Flagship Cream Ale on November 11, 2011 (11-11-11), GreySail Brewing was credited with attracting a younger, year round crowd to Westerly.

GreySail purchased the bright yellow house next door, built by the owners of Westerly Macaroni Co in 1934, leaving its historic murals and light fixtures intact. Despite its fancy digs, the Tap Room is a “proper pub,” with 8 craft beers on tap (four GreySail brews, four “guest” brews).

The Tap Room also features a warren of comfortable “living” rooms, a dartboard room, and an outdoor beer garden where guests can play bocce and cornhole. Food is available from Vetranos Wood Fired Pizza, the perfect pairing for a freshly made beer.

Downtown Westerly RI

SHOP: Downtown Westerly Rhode Island

Fun and funky shops in downtown Westerly are intermingled among Mixed Martial Arts and Yoga Studios, gyms, antique and traditional furniture stores. And restaurants. Among my favorites are:

BOOKS: Savoy Bookshop and Cafe

Followers of this travel blog know that we are huge fans of independent bookstores and will shout our praises from the rooftops (or, just write about them here). The Savoy Bookshop and Cafe, opened in 2016 in the fully restored 1886 Martin House (formerly the Savoy Hotel), has since become a community resource and gem.


The Eagles Nest Gallery features American-made products and is crammed full of Vera Bradley, Brighton, and Rhode Island’s own John Medeiros jewelry. But the best thing about Eagle’s Nest is its generosity towards and acknowledgement of US Military families, with discounts and store items specifically for them.

Woodees and Woodmansee’s

This woman’s clothing boutique stands next to the long-standing (since 1904) Woodmansee’s. It’s also owned by the same family. Woodees is Woodmansee’s younger, funkier cousin, with prices a bit lower as well.


“Founded by Artists, Supporting Artists,” the Artists Cooperative Gallery of Westerly seems more professional than amateur. Stop in for very reasonably priced jewelry, ceramics, photography and paintings.

Best Restaurants in Westerly, Watch Hill

EAT: Ella’s Food and Drink, Westerly

It is rare that a town this small is home to a restaurant so outsized in excellence. But Ella’s Food and Drink is testament to chef/owner Jeannie Rolland’s talent and to Westerly’s sophisticated palette. Culinary Institute of America grad Jeannie, and her husband James, have been in the restaurant business for 25 years.

In 2000, they opened their first restaurant, The Perfect Caper, in Punta Gorda, Florida, where it’s still going strong. Jeannie, a five-time James Beard nominee,  beat Bobby Flay on The Food Network’s “Beat Bobby Flay,” whipping up her fantastic Mussels Frites.

A Connecticut native, Jeannie was eager to return to New England. She and James found this building on a busy street (formerly a neighborhood Italian joint), and transformed it into a modern dining room. Pale grey walls showcase the vibrant folk-artsy paintings of New York artist, David Black.


Each dish here is cooked from scratch, with ingredients sourced either locally or from organic farms all over the country, and worth a trip from anywhere.


EAT: COAST at the Ocean House, Watch Hill

Overlooking all moods of the Atlantic Ocean, COAST is wonderful offseason. This is especially true on blustery days when grey green waves crash on the nearly deserted beach below.

For foodies who’d prefer to observe cooking action over action on the beach, ask for a seat near the demonstration kitchen,  a “hot spot” for sure.

EAT: Olympia Tea Room, Watch Hill

Beach-goers can dine on chowder and fresh-catch at the Olympia Tea Room on the small main street strip on Bay Street, in downtown Watch Hill. A local icon, Olympia celebrated its 100th year anniversary in 2016 and is still going strong.

Westerly RI Hotels

Ocean House Front View Watch Hill RI

STAY: Ocean House, Watch Hill

If you want to be spoiled in the best way possible, come to the Ocean House in Watch Hill RI. You’ll enjoy as civilized and tranquil a shore stay as you’ll find anywhere in the world, with over the top service well worth the pretty penny you’ll spend.

Originally built in 1868, by 2003 the 153- room Ocean House had deteriorated to the point where the top two floors were dangerously uninhabitable. Early fans recall small rooms, shared bathrooms, squeaky plumbing, and warped floors. Most claimed it, however, the “most stunning location in the world.”


One of those fans was New York Investment Advisor and Watch Hill summer resident, Charles Royce. Royce had the heart and resources (raising $140 million) to reimagine the Ocean House as a 49-room Relais & Chateaux hotel.


Too expensive to renovate, the structure was disassembled and rebuilt as an exact historic restoration using 5,000 original pieces. Some of these make up the external clapboard, railings, front door, wavy windows, reception desk and stone fireplace in the lobby.


With a focus on exceptional service and warm hospitality, The Ocean House has been winning over the community and past guests since it reopened in May 2010.

Rooms at Ocean House

Colors and appointments mesh harmoniously with sand and sea. Rooms were designed to feel like a friend’s summer shore home.


Big Wigs should strongly consider renting the 3 bedroom, 3,500 sq ft Morgan Suite (named for the Charles W. Morgan whaling ship in nearby Mystic CT). Owned by Charles Royce himself, this two-floor home within the hotel is outstanding in luxe-nautical décor and high end furnishings.

The lower level features a walk out patio just steps from the beach. With three bedrooms, two bunk beds and pull-out couches, it’s perfect for a multi-generation getaway.

Dining at Ocean House


Overlooking all moods of the Atlantic Ocean, COAST is wonderful offseason, especially on blustery days when grey green waves crash on the nearly deserted beach below. Seasonal breakfast dishes incorporate butternut squash, gingerbread, sweet potato, and other comfort food for cool weather.

Every day, chefs crafts dishes that are creatively conceived, often witty, and ultimately scrumptious. For foodies who’d prefer to observe cooking action over action on the beach, ask for a seat near the demonstration kitchen.


The Ocean & Harvest Spa features eight treatment rooms and is a full-service salon (a huge benefit for on-site weddings). Treatments change seasonally, inspired by both Ocean and Harvest.

Drive a Mercedes Benz

Perhaps the splashiest amenity is complimentary use of one of 4 Mercedes Benz cars on property – either from 7am-5pm or from 6pm-midnight. Yes, complimentary, I said: though first-come first served. I’d consider this the chi-chi-est thing to do in Westerly RI’s Watch Hill village.

Center for Wine and Culinary Arts


Downstairs the new rustic-chic chef’s teaching kitchen space, fashioned with reclaimed Connecticut tobacco barn beams, hosts the Center for Wine and Culinary Arts. The complimentary Wine Tasting class is also very popular.

Fitness Center

The fitness center is State of the Art. Includes TechnoGym equipment and Peloton bike.

Indoor Pool

Swim in the indoor Saltwater Lap Pool.

Private Beach, Cabanas, Food, Programs


Excellent service continues on the wide, clean “guests only” Atlantic Ocean beach. There’s no shortage of chaise lounges, and restaurant service.


Though there’s no outdoor pool here, there is one about 15 minutes away at sister property, the Weekapague Resort, where OH guests can also take advantage of other experiences like ranger-led nature tours.

STAY: Weekapaug Inn  

This sister property to the Ocean House is just four miles down the road. The Weekapaug Inn has been a community center and touchstone for generations of families who summer or live on the Rhode Island shore.

For over 60 years, the Weekapaug Inn was a family resort, with no TV’s or phones in the rooms. Renovated in the early 2000’s the enclave retains its classic Cape Cod design with wrap-around porch. Some rooms offer private decks and plunge-pools and lush views of quiet coves and Quonochontaug Pond, framed by cattails and evergreens.

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  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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