Berlin, Md.
Population 4,600
This is the fictionalized film setting where Julia Roberts was the Runaway Bride, and retirees might consider running to Berlin for its laidback allure. The town’s tree-shaded downtown sports new cafes and boutiques watched over by the hoary Atlantic Hotel that’s been serving guests and diners since 1895. You can toast your leisure years at one of the Shore’s most popular breweries, Burley Oak. There are golfing options galore and a 15-minute drive brings you to Ocean City’s sand and surf.
Niche rating: A for retirees
Lower-cost alternative—A little sleepier and a lot less expensive, Pocomoke City, Md. (pop. 4,000) has been dubbed “the friendliest town on the Eastern Shore” and has a performance arts center carved out of a 1920s movie theater, as well as a riverfront park.
