Historic Princess Anne blends college life with rural charm
Princess Anne is one of the Eastern Shore's historic towns, founded in 1733 and serving as an 18th-century market center with tobacco plantations and river trade on the Chesapeake Bay. Today, historic architecture blends with a vibrant college culture at the University of Maryland Eastern Shore. While the school draws college kids, a peaceful, rural setting draws retirees and others. "It's a slower-paced, small-town kind of vibe with some parks and, of course, nature," says Jennifer Whittington, Realtor with Long & Foster Real Estate, who works across the peninsula. "That's one of the big things drawing people here because they want to escape the hustle and bustle and be able to get out to the Bay."
Preserved historic homes and rental opportunities
Princess Anne's central historic district preserves the town's character with about 270 original structures. They include pre-Revolutionary buildings and a high concentration of Federal, Victorian and vernacular dwellings. "Most of them are in pretty good condition, but some are run down and need to be renovated," Whittington says. Midcentury ranch-style homes and more modern New Traditional homes surround the town center. Many residents rent, and several apartment complexes are near the university. The median home price is about $240,000, lower than many Eastern Shore communities. Properties along the Manokin River may fall within a FEMA special flood hazard area.
Education options range from pre-k to collegiate opportunities
Somerset School District serves the area and earns an overall C from Niche. Kids can attend Princess Anne Elementary School for pre-kindergarten to first grade, Greenwood Elementary School for second through fifth grade, Somerset Intermediate School for sixth and seventh grade, and Washington High School & Academy for eighth through 12th grade. Princess Anne Elementary earns a C-plus while the rest earn a C. Teens can earn early college credits at the nearby University of Maryland Eastern Shore (UMES).
UMES ranks among the top 20 public Historically Black Colleges and Universities, according to U.S. News & World Report. It offers 38 undergraduate and 16 graduate programs in various science, education, engineering and social science fields. The community rallies behind EMES basketball, volleyball and other NCAA Division I teams.
Outdoor fun from Manokin River to Ocean City's shores
Residents enjoy a natural setting and nearby beaches. On the peninsula's east side, Ocean City is a popular tourist destination, while Chincoteague has a quieter waterfront with wild ponies. Princess Anne's Manokin River Park features a playground and covered picnic table on the riverbank. Locals can also launch a kayak and paddleboard. About 20 miles north in Salisbury, the Pemberton Historical Park is a former plantation-turned green space spanning over 250 acres. The park emphasizes history and nature, with a trail system, nature center, restored 18th-century house and ponds with catch-and-release fishing.
Historic hotel restaurant and casual seafood spots in town
In the historic district, Sugar Water is a favorite restaurant for farm-to-table brunch and dinner in the Washington Hotel, which was initially built in 1744. It's one of several historic brick commercial buildings on Somerset Avenue, Princess Anne's Main Street. Other restaurants are clustered on the town's north side around U.S. 13. The family-owned Beach to Bay Seafood serves fresh catches such as soft crab sandwiches and fries. Patrons can order their food to go and sit at the outdoor picnic tables. Food Lion and Dollar General are available for grocery trips in town. Big box stores and dining options are a short drive in Salisbury, Fruitland and Pocomoke City.
Midnight Muskrat Dive rings in the new year
Locals ring in the new year with a Midnight Muskrat Dive—one of the town's most celebrated and quirky traditions. The taxidermied Marshall Muskrat is lowered from a 30-foot structure during the midnight countdown. The celebration includes live music, horse-drawn carriage rides and a sparkling cider toast. The nonprofit Main Street Princess Anne brings seasonal craft fairs and outdoor movies at Manokin River Park. Somerset County NAACP leaders share their knowledge about local Black history during guided bus tours.
Shore Transit buses and highway access support local travel
U.S. 13 is the main drag and leads to Salisbury, about 15 miles north and Pocomoke City, about 15 miles south. While many residents rely on cars, the Maryland State Highway Administration has made pedestrian improvements to the main road. The county aims to further improve pedestrian infrastructure to develop the town into a walkable destination similar to the Eastern Shore town of Berlin. Shore Transit provides bus routes to surrounding towns, including Ocean City. About 15 miles north in Salisbury, TidalHealth is the closest full-service hospital with around-the-clock emergency services.
