Thompson Park and the City center of the historic town of Easton. Image credit grandbrothers via Shutterstock

11 Towns in Chesapeake Bay That Have the Best Main Streets

As United States' largest estuary, Chesapeake Bay encompasses parts of Maryland, and Virginia, West Virginia, Delaware, Pennsylvania, and New York. The whole Bay area boasts over 3,600 species of flora and fauna, making it not only unique in North America, but worldwide. Each of these towns with the best main streets features a unique quirk, ranging from artistic to historic to geographical. These towns strike the perfect balance between the bustle of Cambridge and the rural fishing village of Reedville, an unincorporated community in Virginia.

St. Michaels, Maryland

Some of the shops and stores in St Michaels, MD along the town's main street.
Shops and stores in St Michaels, Maryland, along the town's main street. Image credit George Sheldon via

St. Michaels supplies a colorful set of historical attractions and modern amenities in the downtown area, including Ava's Pizzeria & Wine Bar. Don't miss the must-visit Chesapeake Bay Maritime Museum, showcasing the town's maritime heritage through engaging exhibits and interactive displays. With stunning waterfront views, St. Michaels invites you to enjoy peaceful promenades and boat tours before delving into hidden coves and wildlife sanctuaries. It's ideal for any traveler to explore natural wonders (and who wants a trinket to remember the visit).

Oxford, Maryland

The Robert Morris Inn in Oxford, Maryland. The Inn is the oldest operating tavern in the United States, dating to the 18th century. It was once the home of patriot Robert Morris.
The Robert Morris Inn in Oxford, Maryland. Image credit JE Dean via Shutterstock

Picture-perfect Oxford, Maryland, showcases its charm in the downtown area, with attractions like the oldest-operating tavern in the US, The Robert Morris Inn, and Water's Edge Museum. The iconic Oxford-Bellevue Ferry, operating since 1683, adds a touch of history to the town's appeal. Grab your camera (mental or smartphone) and head to the waterfront for stunning bay views and a serene retreat, engulfing your traveling group in Oxford's irresistible charisma and enigmatic charm. One of the oldest towns in the state, it has a historical touch that just can't be replaced.

Cambridge, Maryland

Cambridge, Maryland US, Blue Ruin restaurant exterior
Cambridge, Maryland, Blue Ruin restaurant exterior. Image credit 010110010101101 via Shutterstock

Welcoming you to its delightful main street adorned with a quaint array of small-town locales such as Blue Ruin restaurant, Cambridge is a must-see for those looking to explore in all senses. The famous Black Water Bakery is a must-visit establishment for sweets to fill your belly. You can enjoy the picturesque waterfront views along the Choptank River, and don't miss the Harriet Tubman Museum and Educational Center to learn about the renowned abolitionist's legacy. With well-preserved architecture and a vibrant culinary scene celebrating the Chesapeake Bay's heritage, Cambridge remains a friendly Maryland nook worth exploring.

Cape Charles, Virginia

Aerial vewi of homes in Cape Charles, Virginia.
Homes in Cape Charles, Virginia.

Cape Charles beckons visitors with its charming main street featuring peculiar gems like the Cape Charles Coffee House. Tourists can relax on impeccable beaches and enjoy the scenic waterfront, perfect for leisurely walks along the Bay. The town's maritime theme is accentuated by its bustling marina, making it a haven for boaters and sailing enthusiasts. It is a great place to chill out, thanks to its waterside energy. Embrace Cape Charles' immaculate historical edifices and flourishing arts community, celebrating the Chesapeake Bay's natural splendor and coastal heritage.

Reedville, Virginia

Ice Cream Sculpture Outside of Chitterchats Homemade Ice Cream Shop
Ice Cream Sculpture outside of Chitterchats Homemade Ice Cream Shop. Image credit Holly Anne Cromer via Shutterstock

Nestled on Virginia's Northern Neck, Reedville infatuates countless travelers. Its maritime heritage meets coastal serenity through locally caught seafood dishes at Tommy's Restaurant, and classic ice cream at Chitterchats Homemade Ice Cream Shop. Afterward, sate your inner water creature with a variety of activities at Smith Point Marina. Take in the scenic waterfront vista during tranquil strolls, and visit the Reedville Fishermen's Museum to learn about the area's fishing traditions and history. The entire area is suitable for those seeking finer things while still endeavoring to explore maritime regions. This is a must-see destination when you're taking a Chesapeake Bay road trip.

Easton, Maryland

Overlooking cars on Main Street, Easton, Maryland
Main Street, Easton, Maryland. Image credit Joseph Sohm via Shutterstock

The Town of Easton exudes charm and history along its beguiling main strip, taking tourists aback with its clever outlay and peaceful atmosphere centering around Thompson Park. It's designed for people wanting to walk through a core area and get the most out of the visit. During the trip, you can discover one-of-a-kind gifts at The Tidewater Inn Gift Shop.

The well-preserved historic buildings showcase the town's storied past, and nature enthusiasts can wander about in the nearby Pickering Creek Audubon Center to witness the region's diverse wildlife and natural beauty. Try and spot the previously endangered Delmarva fox squirrel or velvety sedge and yellow thistle. Time and again, Easton makes its mark as a leading Maryland small town for its cultural riches. Breathtaking and relaxing, this hotspot is a perfect place to take in the blend of human-created main street gems and the panorama of nature's paintbrush.

Chestertown, Maryland

View of the historic town downtown streets of Chestertown, Maryland.
Historic town downtown streets of Chestertown, Maryland.

Drawing visitors with its riveting main street experience, Chestertown is filled with historic charm and modern appeal. Shop for unique gifts and artisanal crafts at Twigs and Teacups, and savor locally inspired dishes at Figg's Ordinary. The annual Chestertown Tea Party Festival commemorates the town's revolutionary history, while the Garfield Center for the Arts hosts live performances and cultural events. For a lively feat that allows you to see the Chesapeake Bay at its best, this main street offers the ideal vibrations for a fun trip or a weekend escape.

Chesapeake City, Maryland

Overlooking Chesapeake City, Maryland, along the Chesapeake and Delaware Canal.
Chesapeake City, Maryland, along the Chesapeake and Delaware Canal. Image credit Jennifer Schmidt via Wikimedia Commons

Chesapeake City, named after the Bay itself, invites you to drift over its character-rich main street dotted with exclusive locales like The Bayard House Restaurant. Adventure through the town's 19th-century buildings and enjoy scenic views of the Chesapeake and Delaware Canal (C&D Canal). The Chesapeake City Bridge, a historic landmark, adds to the town's charm, along with its friendly atmosphere and boating culture. Nautical and natural sum up the virtues of this Maryland gem, where visitors can set their own pace and enjoy the environment.

Rock Hall, Maryland

Sitting by the waterfront in Rock Hall, Maryland.
Waterfront in Rock Hall, Maryland.

Delightful Rock Hall enthralls visitors with its particular infusion of maritime history and coastal charm. Enjoy live performances and local art at Mainstay and discover locally sourced delights at Bayside Market. The Rock Hall Museum showcases the town's maritime heritage, while the annual Pirates and Wenches Fantasy Weekend celebrates its nautical past. The legacy is a thing of maritime legend, so to embrace the great Posseiden, this main street is definitely a spot worth seeing.

Tilghman Island, Maryland

Tilghman Island, Maryland, USA, Lazyjack Inn Bed & Breakfast.
Tilghman Island, Maryland, Lazyjack Inn Bed & Breakfast. Image credit Malachi Jacobs via

Tilghman Island in Maryland offers a concealed treasure right in Chesapeake Bay. Pore over the Main Street wonders such as the Two if by Sea, and savor freshly caught seafood at the Tilghman Island Country Store. Enjoy serene waterfront vistas during a picnic or walk, then take the chance to indulge in the town's fishing traditions at the Tilghman Watermen's Museum. Ideal for those looking for a way to spend casual time with main-street energy, Tilghman Island is ready to provide. It's perfect for those seeking out a three-day weekend that offers a one-of-a-kind fusion of peace and vivacity.

Crisfield, Maryland

Waterfront view of Crisfield, Maryland
Waterfront in Crisfield, Maryland.

Quaint and enchanting, Crisfield, Maryland, stands out with its rich seafood culture and coastal beauty. Sample delectable crab dishes at the Linton's Crab House and dine with waterfront views at the Water's Edge Cafe. Observe fishing boats and learn about the town's fishing industry at the bustling harbor. The J. Millard Tawes Museum preserves Crisfield's maritime traditions and adds to its historical significance. The tradition is steeped into the land, making this a popular tourist attraction that honors the water-faring legacy that birthed its greatness.

Chesapeake Bay is not just a body of water; it's a tapestry of stories and legacies woven through time. Journey through these bewitching places, encapsulating the best main streets in the Chesapeake Bay. It offers travelers the chance to gain a profound appreciation for the region's rich and enduring allure. Whether it's focusing on the quaint storefronts or the maritime museums, each area awaits exploration. Embrace the warmth and hospitality of their communities as you discover the hidden wonders of Chesapeake Bay.

  1. Home
  2. Places
  3. Cities
  4. 11 Towns in Chesapeake Bay That Have the Best Main Streets

More in Places