10 Prettiest Downtown Strips On The Chesapeake Bay
The Chesapeake Bay is the largest estuary in the United States, spanning 11,684 miles of shoreline. It is also one of the nation's most active maritime hubs and is dubbed the "Mother of Waters" because of its many coves and inlets. These pockets of water house many charming and unique towns, many featuring some of the best downtown strips in the Mid-Atlantic Region.
These charming towns' communities embrace their nautical backdrop, often seen from the town's downtown entertainment districts. Most of these regions boast extraordinary colonial history, much of which has been preserved from the Revolutionary War to the Civil War. If you want an entertaining, historical downtown with a coastal atmosphere, these are the 10 prettiest downtown strips on the Chesapeake Bay.
Havre de Grace, Maryland
Havre de Grace is an elegant, classic Maryland coastal town. There is much to do in this historic town, including scenic tours, parks and trails, and cultural museums interpreting the region's history, much of it on the downtown strip. The first stop for those searching for the town's history is the Visitor Center for brochures and walking maps. Nearby, the Havre de Grace Maritime Museum explores the town's economic roots, which are familiar to many cities along the Chesapeake Bay.
Visitors should not miss visiting the Concord Point Lighthouse and Museum. Built in 1827, the lighthouse is the oldest publicly accessible lighthouse on the Chesapeake Bay, and the museum includes unique exhibits that tell the story of this landmark feature. Visitors do not have to stay indoors to view the exhibits here. Downtown has numerous public murals and paintings, including Bald Eagles on the Susquehanna River and the hand-carved Birds of the Chesapeake found atop the pilings near the lighthouse.
Cambridge, Maryland
Like many towns on the Chesapeake Bay, Cambridge has a storied history that can be explored in depth in the Historic Downtown Main Street District. The walkable area is among the best in the state, full of outside dining options, unique finds, and a tranquil atmosphere that includes strings of light after sundown, creating a romantic ambiance. The community adds to the charm and arrives in droves for Second Saturdays, a rotating live music event, and the Long Wharf Farmers Market on Thursdays.
Self-guided tours are welcome through downtown Cambridge, though the adventurous may choose one of the Cambridge Ghost Tours. The town website offers a downloadable walking tour map that leads pedestrians past historical buildings such as 1800 Josiah Bayley's Law Office and the Dorchester Courthouse, built in 1854. Downtown offers the perfect atmosphere to walk back into history by exploring vintage architecture and learning its significance.
St. Michaels, Maryland
St. Michaels is one of the prettiest towns in this region, with a settlement history dating back to the 17th century. It derived its name from a church built in 1672, the Christ Episcopal Church of St Michael the Archangel parish. There is much to do here, from nautical outings to exploring the town's cultural and culinary offerings. St. Michaels Museum at St. Mary's Square features three vernacular buildings in the heart of town that locals call "The Green," providing a look at the city in the 1800s.
The Chesapeake Bay Maritime Museum and Store, on an 18-acre waterfront campus, explores the rich history that played a pivotal role in the region's development. St. Michaels is also a foodie's dream, offering cuisine from fresh seafood to contemporary American. Restaurants include Cafe 401, Lan’s Wine and Tapas Bar, and the sophisticated Theo's Steakhouse.
Oxford, Maryland
Oxford is a former colonial port with stunning architecture and white picket fences on tree-lined roads. The quaint atmosphere is reminiscent of a former time, while downtown remains present with charming inns and taverns like the Robert Morris Inn and Doc's Sunset Grille. The inn includes the Financier Restaurant, a nod to Robert Morris, who spent his childhood on the property and went on to finance the Revolutionary War.
Stroll down the cobblestone sidewalks to discover unique finds like Mystery Loves Company Booksellers. The shop features mysteries set in the Chesapeake Bay area and is a great way to bring a part of Oxford home after a visit. Nearby, Oxford Vintage and Trade specializes in curated collections of antiques and collectibles with a distinctive Eastern Shore flair.
Annapolis, Maryland
Annapolis is famous as the home of the U.S. Naval Academy and Maryland's capital. However, it has a stunning historic district featuring 18th-century brick residences and the domed 18th-century Maryland State House. Known as one of America's prettiest cities, it is one of the best towns to explore along the coast, bridging the past with the present and offering a welcoming community.
It is hard to say the best thing to do in this historic city, but visiting the walkable downtown area is near the top. 300-year-old buildings now house restaurants like O'Brien's Oyster Bar & Seafood Tavern and Luna Blu Ristorante Italiano. You can also start at the top of Main Street and stroll down the hill to the City Dock, where you can grab a cup of coffee while watching ships sail in and out of Annapolis Harbor.
Chestertown, Maryland
Chestertown is one of the most visited destinations on the Delmarva Peninsula, and it is easy to see why. The Historic Chestertown Walking Tour features 29 stops showcasing the preserved homes, some dating back over 300 years, like the River House. Similarly, the Widehall Mansion, a beautiful Georgian mansion built in 1770, overlooks the Chester River on the corner of Water Street and High Street.
Downtown also has stunning historic inns like the White Swan Tavern, epitomizing the town's spirit and charm. Built as a residence in 1733, it was converted to a tavern in 1790. Thankfully, it was turned into an elegant bed and breakfast in the 1970s and is one of the best ways to submerge yourself in the local culture. The culinary scene throughout town is as grand as the bed and breakfast, with sophisticated offerings like The Kitchen at the Imperial.
Solomons, Maryland
Solomons, also known as Solomons Island, is an attractive weekend destination where the downtown area serves as the heart of its many attractions. The compact, walkable district is lined with waterfront restaurants, galleries, and boutique shops, making it ideal for exploration on foot. The Calvert Marine Museum is a standout here, interpreting pre-history, natural history, and maritime heritage through live animals, fossils, and interactive exhibits, and it features a charming cottage-style lighthouse.
Just off the main drag, Drum Point Lighthouse is a meticulously preserved screw-pile beacon that serves as a symbol of the Chesapeake’s maritime past. Downtown Solomons also embraces the arts. The Annmarie Sculpture Garden and Arts Center lies just a short walk from the main corridor, blending indoor and outdoor works like The Council Ring and A Surveyor’s Map, which invite visitors to engage with the interplay between art and nature.
Onancock, Virginia
Founded in 1680, historic Onancock is a tapestry of past and present, and its downtown district is the heart of that charm. The walkable area combines vintage residential and commercial buildings, like the landmark Ker Place, a Georgian-style mansion that immediately sets the tone. Visitors strolling through downtown will find unique shops and historical sites close together, making for a relaxing and immersive experience.
Hopkins and Brothers Store, once a general store, now houses exhibits interpreting the area’s mercantile past. The Waterman's Heritage Museum, located at the Onancock School Community & Cultural Center, further anchors the downtown with its tribute to the region’s watermen. The district has a fantastic amount of history to explore that could easily fill up a relaxing weekend on the coast.
Cape Charles, Virginia
The historic railroad town of Cape Charles features a seven-block historic district containing over 530 historic structures. The downtown district is also part of the Main Street initiative for its preserved architecture and heritage sites. The district includes Queen Anne, Victorian Italianate, Gothic Revival, and other vintage styles popular between 1880 and 1920, and it is available for walking tours.
Much of the town's history can be studied at the Cape Charles History Museum, which features exhibits from the railroad era and tours of several notable buildings. Other noteworthy sites are the 1886 Seafood Headquarters, the 1910 Jack Moore House, and Eyre Hall. Littleton Eyre purchased the hall in the mid-1700s and has remained in the family. It is also one of the best-preserved homes on the Barrier Islands and a must-see for history and architecture buffs.
Yorktown, Virginia
Yorktown is one of the most historic sites along the coast and one of the original shires formed in colonial Virginia in 1682. The entire town is a veritable living history museum of American history, featuring many museums and preserved sites. Attractions include the American Revolution Museum of Yorktown, the Victory Monument, and the Watermen's Museum. From learning about battles that took place in the Old Dominion to the annual chili cook-off in the Watermen’s Museum, there is much to see and do.
The charming town offers several ways to explore, such as the Yorktown Trolley system or joining the Patriot or Steam Wagon Tours. LOVE letters are also a unique way to experience the town. The monument is in the center of the Riverwalk Landing and stands over six feet tall and 16 feet wide. It is one of 300 permanent love letters throughout Virginia, embodying the state's motto, "Virginia is for Lovers."
Downtown Exploration Along The Chesapeake Bay
From historic towns like Yorktown to quintessential military cities like Annapolis, these ten towns have the best downtown strips on the Chesapeake Bay. The districts make the best of the scenery by incorporating local businesses and eateries a stone's throw from the historic estuary. Whether visitors are looking for a romantic getaway or a long shopping weekend, these coastal towns have it all.
What makes the main drags unique is their abundance of heritage sites, things to do, and elegant restaurants with waterfront views. Booking a room downtown is the best way to immerse yourself in the local culture and stay a short walk from the main venues and sites. Many of these towns, like Chestertown, are pedestrian and dog-friendly, an ideal way to explore the area's significance and charm.
