6 Safest Small Communities To Settle In Chesapeake Bay

The beautiful Chesapeake Bay watershed spans 200 miles across portions of six states and Washington D.C. Maryland and Virginia account for almost all of the Bay’s shoreline, and violent crime rates in each state are near or below the national average overall, even as some larger population centers report higher numbers. This article focuses on smaller Chesapeake Bay communities under 50,000 residents whose aggravated assault and homicide rates generally track at or below their state and U.S. rates over recent years, with only occasional spikes. These towns pair relative safety with waterfront settings, walkable streets, and a wide range of local activities.

St. Michaels, Maryland

The beautiful town of St. Michaels, Maryland is home to just over 1,000 people who enjoy a laid-back lifestyle. Recent data show that St. Michaels’ violent crime rate, including aggravated assault and homicide, remains low in absolute numbers and generally below or roughly in line with statewide and national violent crime rates for small towns of similar size. While in town, visitors can step into the past at the Chesapeake Bay Maritime Museum, known for its historic boats and working waterfront setting. During the warmer months, Patriot Cruises offers narrated historical trips along the Bay that provide local context while you’re out on the water. Back on land, Foxy’s Harbor Grille is a popular stop for a casual meal before heading out to hike the St. Michaels Nature Trail, which stretches just over a mile and highlights coastal habitats found throughout the region.

White Stone, Virginia

With a population of just under 400 people, White Stone is one of the smaller communities in the Chesapeake Bay area. In Virginia, violent crime occurs at a rate well below the national average overall, and in a town this small, aggravated assaults and homicides remain rare events, keeping local risk levels below broader state and national benchmarks over recent years. Visitors can stroll along the banks of the nearby Rappahannock River before stopping for a coffee and donut at the Chesapeake Donut Company. The Allure Art Centre, originally built as a private home in 1901, displays work from regional artists in a gallery setting. Founded in 1715, White Stone has a long history that is evident as you walk its streets, where historic churches and traditional Southern architecture somehow calm you and stimulate your imagination at the same time.

Oxford, Maryland

Founded in 1630, Oxford is one of Maryland’s oldest towns and today has fewer than 1,000 residents. Although Maryland’s overall violent crime rate sits slightly above the national average, small communities like Oxford report very few aggravated assaults or homicides, leaving local rates below state and national figures in the most recent years. Named after Oxford, England, the town retains much of its historic character, with waterfront streets and marinas that often appear in Chesapeake Bay photography. The Oxford Museum offers a free self-guided historical walking tour, complete with a map and audio clips covering dozens of historic buildings throughout town. After a day of walking, Doc’s Sunset Grille provides a waterfront spot to eat. Shoppers looking for unusual gifts can browse The Treasure Chest, a longtime local favorite.

Kilmarnock, Virginia

Founded in 1650, Kilmarnock is one of the safest and most relaxed communities in the Chesapeake Bay area, with a population of around 1,300 residents. Virginia’s violent crime rate is lower than the U.S. average, and Kilmarnock’s small size and low counts of aggravated assaults and homicides help keep its risk level near or beneath broader benchmarks over time. Originally known as “The Crossroads,” the town developed as a gathering place for surrounding communities. Today, visitors can learn about local history at the Kilmarnock Museum before enjoying a meal at Lee’s Restaurant, a longtime local favorite. The Kilmarnock Antiques Gallery offers a wide range of vintage items and collectibles. Town Centre Park provides space for walking, jogging, and community events held throughout the year.

North Beach, Maryland

Incorporated in 1910, the town of North Beach has long drawn people to its shoreline setting. With just over 2,000 residents, North Beach reports low counts of violent crime, and recent data show years with no aggravated assaults and no homicides, keeping its violent crime rate at or below Maryland and national levels when adjusted for population. Residents and visitors spend time at the Mark R. Frazer Sunrise Garden, located near the center of town and featuring ponds, a waterfall, floral plantings, and a gazebo. The Bayside History Museum documents the town’s past, while the beach, fishing pier, and boardwalk remain popular gathering spots. Local theater productions are staged at the Twin Beach Players theatre, offering another way to engage with the community.

Chestertown, Maryland

Chestertown, Maryland, sits along the Chester River on the upper Eastern Shore and has a population of roughly 5,000 residents. Although Maryland’s overall violent crime rate is slightly higher than the national average, Chestertown’s recent aggravated assault and homicide rates tend to stay at or below statewide and national levels for towns of comparable size, with occasional spikes. As a designated Arts and Entertainment District, Chestertown features brick streets and colonial-era architecture often photographed along the Bay. Visitors can explore the historic downtown and waterfront, walk along the Chester River, or browse shops and galleries on High Street. The Garfield Center for the Arts hosts performances, and Washington College contributes cultural programming and walking paths. On market days, the Chestertown Farmers’ Market brings together local growers and artisans.

Life Along the Bay

To some, Chesapeake Bay is simply a geographic feature, but for many, it is a place to settle and stay. These Maryland and Virginia communities show that it is possible to find small towns where crime is not a great concern, while daily life stays closely tied to the water and local history. Across the region, residents have access to boating, seafood, cultural events, and long-established neighborhoods. For the right person, these communities offer a comfortable and lasting place to call home.