5 Reasons to Love Westerly in Winter

Westerly, the westernmost town in Rhode Island and the first town you come to if you’re heading east from the Connecticut shoreline, is proof that you don’t have to travel far to find destinations worth exploring. The town is relatively large, but it’s made up of numerous small villages, each with its own distinct atmosphere. This makes Westerly as a whole feel somewhat disjointed, but it’s a major plus for visitors; within minutes, you can go from a bustling downtown to a waterfront historic district to an unspoiled natural landscape, without leaving town.

Summer is Westerly’s high season, when the beaches fill up early, the souvenir shops open, and hordes of people flock to be by the sea. But when the season ends, the waterfront businesses lock their doors, and the last lines of cars file out of the pricey parking lots, the town becomes a quiet coastal paradise for those willing to seek out its subtler attractions.

There are many things to love about Westerly in the winter. Here are five of them.

Napatree Point

The Napatree Point Conservation Area (Fort Road) is a beach and wildlife refuge in the village of Watch Hill. To access this sandy strip of land at the very edge of the Rhode Island coast, climb the dune behind the parking lot. You’ll emerge above one of the most gorgeous views in southern New England. On one side is the shelter of Little Narragansett Bay; on the other, the Watch Hill Lighthouse blinks in the distance. And straight ahead, the sand curves towards a point far in the distance. Napatree covers 86 acres, and the walk to the end of the beach is about 1.5 miles. If you go all the way, you’ll find the ruins of the late-19th century Fort Mansfield, the only remaining clue that humans once inhabited this stretch of coastline. It’s hard to imagine today, but years ago, a row of summer cottages stood lined up along the water. The Great Hurricane of 1938 changed that, sweeping whole houses into the surf, killing 15, and transforming the shape and character of the beach. That was not its first transformation; when Dutch trader and explorer Adriaen Block first saw it, it was heavily forested, inspiring its name. Today, with the trees, houses, and fort gone, there are only dunes and dune grass, sand and water, sky and birds. There are beautiful beaches all along Westerly’s coast – some small, some large, some private, some public – but Napatree is special. And the off-season, when the crowds are gone and the parking is free, is the time to see it.

Coastal Villages

Today, Watch Hill is best known as a byword for subtly displayed wealth and the home of the oft-Instagrammed Ocean House hotel. (Oh yeah, also, Taylor Swift lives here.) But the village’s history goes back long before that. The statue of Niantic sachem Ninigret, located in a small waterfront park, is a nod to the area’s 17th century inhabitants. The small shops along Bay Street, closed for the off-season, and the vast waterfront “cottages,” now year-round homes, evoke the late 19th century, when Watch Hill was a summer resort for the era’s 1%. The Watch Hill Lighthouse (Lighthouse Road) has a dramatic history of its own. Though the adjacent museum is only open seasonally, winter visitors can still walk to the lighthouse grounds and watch the waves crashing against the rocky coast nearby. 

A short distance away is the village of Weekapaug, where you’ll find more sweeping coastal views and impressive beachfront property. Drive down Noyes Neck Road towards Weekapaug Point and then along Spray Rock Road and Wawaloam Drive to get a good look at this stunning stretch of coast. (Bonus: unlike some similar areas, there are parking spots here.)

Perhaps the area of Westerly that changes most from summer to winter is Misquamicut. Most Connecticutians have a Misquamicut story (mine involves being evacuated from a beachfront motel and trying to drive faster than an impending hurricane.) But in the off-season, the very popular Misquamicut State Beach is simply a vast expanse of sand and sky. Its sprawling parking area is empty, save for a few cars and an off-duty ice cream truck, and main drag Atlantic Street, parallel to the beach, has an abandoned quality, eerily photogenic if you like that kind of thing.

Downtown Westerly 

The commercial center of Westerly, where High Street, Canal Street, and Route 1 converge, looks and feels like an old-fashioned small town Main Street. It’s the kind of downtown that invites you to stop for a while, browse a few independent shops, try out a restaurant or two, and admire the eclectic architecture. My personal favorites here are the swanky Savoy Bookshop & Cafe (10 Canal Street), which is so lovely that it snuck into my recent post on Connecticut bookstores despite being in Rhode Island; Wilcox Park, a serene 18-acre Victorian-era square of public space behind the town library; and the collection of vintage-style, local history themed murals that decorate the brick walls of downtown Westerly and neighboring Pawcatuck, CT. Walk across the Pawcatuck River (and the state line) to see how the two areas blend into one attractive riverfront district.

Nature, Beyond the Beach

When you picture the natural beauty of the Ocean State, it’s easy to imagine the coast. But in Westerly, home of some of Rhode Island’s best known beaches, preserved natural areas are just as likely to be farms and woodlands. At the Avondale Farm Preserve (Grassland Way) in the quietly charming little village of Avondale, an easy walking path bisects 50 acres of grassland and salt marsh beside a small historic farm. It was the first property acquired by the Westerly Land Trust, which now owns over a dozen such preserves, featuring many miles of trails through diverse habitats from woods to bogs to freshwater wetlands. The Westerly Town Forest (Laurel Avenue) provides another green space that’s open to the public. Even if trail walking or hiking isn’t on your itinerary, simply driving around will take you past stone walls, open fields, and other pastoral vistas you might not expect to see in this coastal town.

Unexpected History 

The history of Westerly, like that of any New England town, stretches back through the centuries and can be glimpsed almost anywhere you look. The Perry Homestead Historic District (Margin Street and Beach Street), on the picturesque bank of the Pawcatuck River, consists of six Colonial and Classical Revival homes built for the prominent Perry family. (The most famous members of which are Rhode Island natives Oliver Hazard Perry and Matthew C. Perry.)

The small coastal village of Shelter Harbor was founded in the early 1900s as Musicolony, a retreat for New York opera singers and artists. Today, it looks like any coastal enclave – until you notice the street names. Drive past the Shelter Harbor Inn (10 Wagner Road) and from there, navigate the small grid of residential roads; you might turn onto Handel or Bach, glance down Grieg or Liszt, or admire the waterfront homes on Rossini.  

Further north, the Bradford Village Historic District (in Westerly and Hopkinton) showcases what remains of a thriving 19th century mill village. At 460 Bradford Road, the sprawling Bradford Mill Complex overlooks the Pawcatuck River. Its oldest building dates from 1864. On Bowling Lane, 41 double houses, built for mill workers, still stand. (There’s older history here, too: for instance, the 1789 Solomon P. Wells house (24 Church Street) shows a different facet of an older New England.) 

Not far away, in the village of White Rock, another hulking old mill (84 White Rock Road) is both a reminder of the region’s past – it was built in 1849 as a cotton mill – and an emblem of its present. Today, the striking brick building is home to Griswold Textile Print, which produces hand-printed fabrics. Like the murals downtown and the “cottages” in Watch Hill, it’s a reminder of how Westerly’s history has shaped it into the place it is today. 

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