Start from 24 curated places around Watch Hill, RI, then choose the recommendations that fit your guests.
Restaurants & cafés
Olympia Tea Room
Watch Hill's most storied dining room, open since 1916 and perched above the harbor at the center of Bay Street. The menu is modern New England — lobster bisque, grilled fish, house-made pastas — paired with an award-winning wine list. Every table has a line to the water; the west-facing deck catches one of the best sunsets in Rhode Island.
The Cooked Goose
The beloved breakfast and brunch stop on Watch Hill Road, just before the village. A casual, counter-service cafe known for hearty omelets, fresh sandwiches, Cobb salads, and house-made key lime pie. Lines form on summer mornings, and most people take their food to a nearby bench or the beach.
Trails & outdoors
Napatree Point Conservation Area Trail
A 3.1-mile out-and-back (or partial loop) along the Napatree Point barrier spit, rated 4.6 stars on AllTrails from nearly 1,000 reviews. The trail is almost entirely oceanside — one side faces Little Narragansett Bay, the other the open Atlantic — with Fort Mansfield ruins at the far end and exceptional shorebird and migratory bird watching throughout. The terrain is flat, sandy, and accessible for most fitness levels.
Dr. John Champlin Glacier Trail
A 2.3-mile easy trail through Westerly's glacially sculpted interior, rated highly on AllTrails from 727 reviews. The park covers 134 acres of kettle ponds, kame ridges, carved canyons, and glacial erratic boulders left by the last Ice Age. Elevated sections offer sweeping views over Winnapaug Pond toward Block Island Sound. Interpretive signs explain the glacial geology throughout.
Things to do
Watch Hill Outfitters — Kayak Rentals
A downtown Westerly bait-and-tackle shop that also rents kayaks, with a private launch right behind the Main Street store onto the Pawcatuck River. Single, tandem, and sit-on-top kayaks come with paddles and life jackets, and the calm, flatwater river is beginner-friendly, winding past the Westerly–Pawcatuck waterfront and connecting downstream toward Little Narragansett Bay.
Paddle Surf RI
Based at Misquamicut, Paddle Surf RI offers stand-up paddleboard and kayak rentals for both the ocean and the adjacent Winnapaug salt pond. Lessons and guided tours are available, making it the best entry point for first-timers who want instruction. The pond option is especially good for families with young children looking for calm, sheltered water.
Landmarks & sights
Flying Horse Carousel
Built around 1876 and continuously operated ever since, this is the oldest surviving flying horse carousel in the United States and a National Historic Landmark. The 20 hand-carved wooden horses hang on chains from a central frame and swing outward as the carousel spins — true 'flying' horses. Only children under roughly 12 can ride, but the craftsmanship and history make it a must-see for all ages.
Watch Hill Lighthouse
A working federal lighthouse at the southwestern tip of Rhode Island, first established in 1808 and rebuilt in its current granite form in 1856. The grounds are open year-round for panoramic views across Fisher's Island Sound to Long Island and Connecticut, and the adjacent lighthouse keeper's museum opens for limited summer hours with artifacts, Fresnel lenses, and logbooks.