Known for: historic charm, quiet atmosphere, shopping, great views
Good for: families, couples, nature-lovers, bird watchers
This historic village is actually a part of the town of Westerly, but it enjoys a reputation as a resort town unto itself. It is the southernmost town on mainland Rhode Island, and contains the westernmost point in the state, Napatree Point.
Both secluded and affluent, Watch Hill is considered a quieter resort town than more trafficked destinations like Narragansett and Newport. The 629-acre historic district at the center of town is listed on the National Register of Historic Places. More humorously, Lisa Birnbach, author of 1980’s The Official Preppy Handbook, cited Watch Hill as an acceptable summer destination for preppies in her 2010 follow-up True Prep.
Watch Hill sits on a small peninsula in the Block Island Sound; Napatree Point is a narrow spit of land that juts out from its western side, forming Little Narragansett Bay. Watch Hill’s geography made it a key lookout point (hence its name) guarding the Long Island Sound during the Revolutionary War and French-Indian Wars, and it was home to a short-lived military installation in the early 1900s, Fort Mansfield.
Today, the village is known for its grand mansions overlooking the ocean and its quaint feel. The town center is a seasonal boomtown, with many local institutions like the Ocean House resort, the Olympia Tea Room, and the famed ice cream shop St. Clair Annex hosting flocks of visitors throughout the summer. Though its secluded location provides a welcome respite from noisier tourist destinations, it is also an easy jumping off point for exploring Westerly’s Misquamicut Beach area, neighboring Charlestown, and nearby Connecticut attractions like the casinos and historic Mystic Seaport.