Havre de Grace, Md.
The waterfront of this Harford County river town, where the Susquehanna meets the Bay, sports perhaps Maryland’s largest boardwalk west of Ocean City. The community’s cute and walkable downtown has numerous eating options, parks, a historic district, and a plethora of marinas to dock your boat. Despite the small-town feel, Baltimore’s big-city attractions (and big-time medical facilities) are only 45 minutes away. You can even catch a train to Baltimore and Washington from nearby Perryville (where there is also a casino). Havre de Grace is French for “Harbor of Grace” and while the community was attacked and plundered by the British in 1814, it has enjoyed peace and grace ever since.
AARP Livability: 61
Niche rating: A- overall
Eastern Shore alternative—Chesapeake City, Md. (pop. 700) also has a historic district, waterfront dining
and small-town appeal—all about 30 minutes from Wilmington, Delaware. It earns high marks for outdoor activities and nightlife.