If there was a run-off for all-American town, Bristol would be a finalist. The main street is festooned with flags left waving after the city’s annual Fourth of July parade, the oldest in the country. The street itself is a vibrant vision of what main streets once looked like before malls, with boutique stores and storefront cafés interspersed with solid granite buildings and picturesque colonial homes.

From the beginning, Bristol has had a contentious history. It was founded after King Philip’s War on land near the site of King Philip’s camp, and soon became an important seaport, active in the triangle trade that imported countless slaves from Africa. Because of its strategic importance and Revolutionary sympathies, the town was repeatedly bombarded by British cannons during the Revolutionary War. Along with neighboring Warren, Bristol was partially burned in 1778 by a party of 600 British soldiers and Hessian mercenaries in the lead-up to the Battle of Rhode Island.

While never as well-to-do as Newport, Bristol’s heyday as a shipping center after the Revolution led to many fine Victorian mansions and gardens being built on the outskirts of town. After the slave trade was made illegal in the early 1800s, Bristol’s main source of income was cut off and the town went into temporary decline. It was rescued by a rubber refinery that made boots and clothing, as well as a boatbuilding industry that made both steamboats and yachts. The latter was compliments of the Herreshoff brothers, famous for creating the racing ships that helped the United States win the America’s Cup sailing race year after year.