8 Most Charming Cities in Chesapeake Bay

Spanning about 4,479 square miles, Chesapeake Bay is the longest estuary in the United States. It runs through the mid-Atlantic area, with the Delmarva Peninsula dividing it from the Atlantic Ocean. Parts of this peninsula include Maryland, Virginia, and Delaware. Many of the closest cities to the bay reside in Maryland, offering bustling and vibrant cities full of coastal charm. These cities along the Chesapeake Bay provide endless opportunities for outdoor pursuits, downtown nightlife, and scrumptious east-coast cuisine.

Baltimore

With looming skyscrapers with water views, take in a mixture of high-energy city life and peaceful moments by the bay. Baltimore brims with history, arts, and culture. Fall in love with state-of-the-art pieces at the Baltimore Museum of Art, located at 10 Art Museum Drive. Open from 10:00 a.m. to 5:00 p.m., view contemporary paintings and sculptures, as well as historical artifacts. After, take a stroll to Inner Harbor, an 18th-century port. Located in the heart of the city, it boasts a 7-mile walkway. Walk along Patapsco River and enjoy the sound of waves and gleaming boats or walk further into the downtown core and stop at boutique malls and stores such as Sound Garden, which sells used records. Or perhaps try Baltimore Clayworks, which sells handmade mugs from local creators!

Waldorf

Waldorf continues to grow in population, making it the fourth most populous area in the state. While quiet suburbs reside on the outskirts of the city, the city’s core overflows with activities. Many people flock to one of the city’s main malls, St. Charles Towne Center. Technically, it resides in St. Charles, but it is only a four-minute drive from Waldorf down the US-301 S. While the mall contains popular brands, it also houses boutiques like Casa Furniture and Gia Candle Bar. Additionally, walk around St. Charles Lake Trail, located on Bluebird Drive. Take to the boardwalk and view the expansive forests and marshland!

Silver Spring

Silver Spring is a hub for shopping, restaurants, family activities, and entertainment, which is pretty much everything needed in a city! Nestled among the concrete is Acorn Park, a slice of nature and history. The park includes the remnants of Francis Preston Blair’s estate, Silver Spring. While it is the name of the city, it originates from Francis finding the spring in 1840. Additionally, experience a unique art monument: The Arc. Located at 1203 Fidler Lane, the sculpture consists of rocks from the Arizona desert. The courtyard it sits upon has benches for you to relax and contemplate the structure. Silver Spring offers attractive eateries and stores too. All Set Restaurant and Bar offers nutritious American cuisine, such as seafood pasta and black bean quinoa burgers. Shop at Aday Abeda Market, which sells a mixture of Ethiopian goods. It is a shopping experience authentic to Silver Spring, so plan to make a stop!

Ellicott City

Ellicott City has been around since 1772, being founded by the Quaker brothers, who controlled the city’s mills. The city houses the oldest train station in the United States, making the city a popular attraction for railway enthusiasts. In 1831, the station was built, becoming a part of the B & O Railroad. With a red Ellicott City sign painted on an old overpass railroad track, this city boasts a homey, comforting feeling. Not only does it contain history inside, but outside too. Visit Number Nine Trolley Trail and walk, run, or bike in the woods on boardwalks. Spanning 2.5 miles, it starts around the Patapsco River. Experience lush forests, old railroads, and sedimentary walls of rock. Some fun activities to partake in include ax throwing at Axgard and making personalized clay items at Clayground Studio and Gallery. End the day at Manor Hill Tavern, which specializes in oven pizzas and farm-fresh beer.

Frederick

If wanting to be charmed by the outlines of mountains, then look no further than Fredrick. In Frederick County, there are a total of 28 mountains, with the most prominent being Catoctin Mountain and Sugarloaf Mountain. The public can view this majestic landscape in Catoctin Mountain Park. The park is in Thurmont but is only a 30-minute drive from the city. In the park, explore the 25 miles of hiking trails, ride on horseback, and fish for trout. Alternatively, stay in the city and admire the mountains from a distance while enjoying the Civil War history, wineries, and restaurants.

Columbia

Feel like busting a move? As luck would have it, Columbia has a lively music and entertainment community. Merriweather Post Pavilion is a 40-year-old attraction where musicians of all genres perform. Chrysalis Amphitheater also houses the symphony and other community events. Community is a strong facet of this city, and visitors can join people at Color Burst Park for group exercise classes and concerts. For a nature experience, explore the Columbia Association Robinson Nature Center, which contains 3,600 acres of trails for walking and biking. This park offers a mobile app so hikers can track their own location on the trails and not get lost.

Germantown

With Baltimore 48 miles away from Germantown, this bustling city is technically six villages that boast shopping centers, restaurants, and entertainment activities. For an artistic and cultural experience, visit Black Rock Center for the Arts and catch a live musical theater performance. Inside houses various art exhibits, and if visitors desire to expand their creative skills, they even host classes for kids and adults! For some relaxing outdoor time, experience Great Seneca Stream Valley Park on Watkins Mill Road. Full of rocks, bridges, streams, and lush vegetation, this park offers a peaceful getaway. It covers 1,557 acres and has nine sections.

Rockville

Nothing beats a good town square at the heart of a city, and Rockville certainly has a memorable one. At Rockville Town Square, enjoy the city’s architecture while relaxing in the fresh air. It contains artistic sculptures, cobblestone streets, murals, and local shops. Some stores include Dawson’s Market and Cutesy Celebrations. Afterward, grab a bite to eat at Bonchon Chicken and experience Korean cuisine like never before. A must-see park is Rock Creek Regional Park, with 1,800 acres of lush trees and fishing settings. It contains Lake Frank, covering 55 acres. Technically, this park is in Derwood but is only a 15-minute car ride away from Rockville.

The Chesapeake Bay area offers a charming and unique experience. Full of history, this area offers bustling city life, one-of-a-kind shops, and peaceful nature adventures. Get the best of both worlds: exploring nature during the day and enjoying city activities during the evening. No matter which city folks travel to, they are sure to be charmed by all its attractions and many unique things to do!