Westerly Travel Guide: Things to Do, Best Time to Visit & Itinerary

Westerly is a town of dual personalities, perfectly stitched together by the winding Pawcatuck River and the crashing waves of the Atlantic. On one side, you have the historic downtown, a place where granite quarries once fueled the economy and where a vibrant arts scene now flourishes in red-brick industrial buildings. Just a few miles south, the atmosphere shifts to the salt-washed luxury of Watch Hill and the retro summer fun of Misquamicut, creating a destination that feels like two vacations in one.

Whether you are looking to walk in the footsteps of Taylor Swift and Gilded Age tycoons or simply want to eat a clam cake with your toes in the sand, Westerly delivers. The air here smells of salt spray and blooming hydrangeas, and the sound of the ocean is never far away. It is the gateway to New England’s coast, offering a warm welcome that feels both upscale and undeniably local.

The Soupy Capital of the World

While the beaches get the glory, Westerly’s soul is found in its unique culinary heritage. This town is the unofficial world capital of “Soupy” (a corruption of soppressata), a dry-cured sausage brought here by Calabrian immigrants in the late 19th century. You won’t just find it in delis; it’s on pizza, in omelets, and serves as a point of fierce local pride. Exploring the local food scene here isn’t just about seafood; it’s about tasting a century of Italian-American history.

Beyond the food, the town serves as a cultural borderland. Sitting directly on the Connecticut line, separated only by the river, Westerly absorbs the best of both states. It combines the maritime tradition of the Ocean State with the wooded, river valley charm of eastern Connecticut. This convergence makes for a landscape that is surprisingly diverse, ranging from barrier beaches to deep, quiet woodlands perfect for hiking.

The Icons You’ll Want to See

Watch Hill Lighthouse - Located at the tip of the peninsula, this active aid to navigation has been a beacon since 1807. While you cannot climb the tower, the grounds offer free access and some of the best sunset views on the East Coast. Parking is scarce, so walking from the village center (approx. 0.7 mi) is recommended.

Wilcox Park - This 14-acre walking park in the center of town is an arboretum and a masterpiece of landscape architecture. It hosts major events like the Summer Pops and Shakespeare in the Park. Entry is free, and it is open from dawn until dusk.

Ocean House - A faithful reconstruction of the original 1868 hotel, this yellow giant dominates the Watch Hill bluff. It is one of only 13 triple five-star hotels in the world. Visitors can access the restaurants and spa, though prices are in the luxury range ($$$$).

The Flying Horse Carousel - Located at the end of Bay Street, this is the oldest flying horse carousel in the country, dating back to 1876. The horses are suspended from chains, swinging outward as the ride speeds up. Rides are inexpensive (under $5), making it a budget-friendly piece of living history.

Planning Your Visit

Westerly is easily accessible via I-95, sitting roughly halfway between New York City and Boston. For those preferring rail, the Amtrak station is located right in downtown, making it one of the few beach towns you can easily visit without a car, though having one helps for reaching the beaches. If you are flying, T.F. Green Airport (PVD) in Providence is about a 45-minute drive away.

When packing, remember that the coast is almost always cooler than the inland areas. Even in July, a sweatshirt is essential for evening beach walks. If you plan to visit Watch Hill, be prepared for strict parking rules; public lots can cost upwards of $40-$50 on peak weekends, so arrive early or utilize the trolley system that runs from downtown during the summer months.

While summer is undoubtedly the main draw, don’t sleep on September in Westerly. The “Local’s Summer” offers the warmest water of the year, zero wait times at restaurants, and the stunning backdrop of New England fall foliage beginning to turn, making it the secret best time to visit.