Top 10 Beautiful Chesapeake Bay Towns & Cities on the Shore

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Map of the Best Chesapeake Bay Towns

Chesapeake Bay Towns on the Mainland

Solomons Island, Maryland

Recommended by Us!

Solomons Island has so much to offer in this relaxing, fun, and small town. Chesapeake Bay towns like this are what make this area the world-class destination that it is. What’s great about Solomons Island is that it’s a short drive from large cities, only 2 hours from Richmond, VA, and 1.5 hours from Washington, DC. You can escape the city and enjoy a relaxing getaway for the weekend!

Solomons Island has an amazing culinary scene centered around seafood, with live music and drinks. The town also offers a rich maritime history and numerous ways to get out onto the Bay. So, whatever type of vacation you’re looking for, Solomons Island has it.

When planning your meals, be sure to dine at Island Hideaway, a family-owned and operated bistro and bar with beautiful water views. Everything here is made from scratch, and we especially loved their seafood, Cannelloni, which was stuffed with local seafood! After dinner, head to The Tiki Bar for an Orange Crush and some live music! Thanks to these great dining places, it’s one of the best waterfront towns!

During the day, walk the boardwalk, visit the Calvert Marine Museum, and explore Calvert Cliffs State Park. But we especially recommend you save some time to hit the water! We recommend taking a fishing charter out for those who like to fish. Or, for a more relaxing trip, you can’t go wrong with a sunset sail from Chesapeake Charters. If you’d prefer to get out alone, check out this kayak rental and explore Back River, stopping at the Calvert Marine Museum dock for a break!

State: Maryland
Closest Major Airport: Ronald Reagan Washington National Airport (DCA)
Where to Stay: Solomons Victorian Inn

Annapolis, Maryland

Recommended by Pamela of The Directionally Challenged Traveler

One of the best places on the Chesapeake Bay that is often overlooked by travelers is the beautiful city of Annapolis. Known as America’s Sailing Capital, Annapolis boasts stunning waterfront views, historic architecture, and an energetic cultural scene. The town’s cobblestone streets and picturesque harbor create a postcard-perfect setting that invites you to relax and explore.

This historic town is conveniently located about 30 miles east of Washington, D.C., and 25 miles south of Baltimore, making it easily accessible by car. While driving offers flexibility, you can also reach Annapolis via public transportation, with bus services connecting to nearby cities. A car isn’t necessary as Annapolis is highly walkable, and many attractions are within a short distance of each other.

Start with a visit to the U.S. Naval Academy, where you can take a guided tour and learn about both the history and traditions of this prestigious institution. Stroll through the historic district, where beautifully preserved 18th-century buildings house charming boutiques, galleries, and cafes. You’ll find plenty of free things to do in Annapolis! After a day of exploration, head to the renowned restaurant Cantler’s Riverside Inn for the freshest Maryland blue crabs and other seafood delicacies. This local favorite offers an authentic taste of the city’s maritime heritage and provides a perfect ending to your time in Annapolis.

State: Maryland
Closest Major Airport: Baltimore-Washington International Airport (BWI)
Where to Stay: The Annapolis Waterfront Hotel

Virginia Beach, Virginia

Recommended by Denise from Chef Denise

Virginia Beach’s unique location at both the mouth of the Chesapeake Bay and the Atlantic Ocean offers visitors many opportunities for fun-filled beach days, beautiful nature hikes, and some of the best food in Virginia. Which is why it had to be included on the list of the best Chesapeake Bay towns you should visit!

The Guinness Book of World Records lists Virginia Beach as having the longest pleasure beach in the world. It stretches for miles along the oceanfront and is a wonderful place for just about any water sport and soaking up the sun. The sandy beach also offers a cement boardwalk lined with resorts and restaurants. Be sure to enjoy the miles of shoreline during your stay!

For less touristy eats heading away from the boardwalk is best. If you’re looking for a casual local meal in a fun atmosphere, then head to the Leaping Lizard for sweet potato ham biscuits. For fancier fare, Steinhilber’s on the lake will fit the bill.

Nature lovers will want to visit the two state parks in Virginia Beach, False Cape State Park and First Landing State Park, as well as Pleasure House Point Natural Area, a 118-acre wildlife habitat of marshland that bird watchers will especially enjoy. There’s something for everyone in this Chesapeake Bay town!

State: Virginia
Closest Major Airport: Norfolk International Airport (ORF)
Where to Stay: The Historic Cavalier Hotel and Beach Club, Autograph Collection

Chesapeake Bay Towns on the Eastern Shore

Oxford, Maryland

Recommended by Us!

Oxford, Maryland, the postcard of America! Just stroll down the main street, and you’ll see why! The town has many old homes and businesses with perfectly manicured lawns with white picket fences. We loved the hundreds of year-old homes and the small-town culture that makes Oxford perfectly tranquil. It’s one of our favorite Chesapeake Bay towns for that very reason!

You can plan an entire trip to Oxford or add it to your Eastern Shore road trip. This small town has so much to offer, and you’ll be so glad you stopped by.

It’s located on the eastern shore of Maryland, at the mouth of the Tred Avon River in Talbot County, which means you’ll be blessed with sunsets over the water. That’s always a plus! But the town itself is why you’ll want to visit. There are a few different adorable inns located right on the water where you can stay a few nights at the Robert Morris Inn or The Oxford Inn.

Oxford might not have a ton of restaurants to choose from but don’t worry, the ones they do have are incredible! Pope’s Tavern serves Italian fare with homemade pasta and ricotta cheesecake. Or, if you’re looking for seafood (you are on the water, after all!), look no further than Docs Sunset Grille to pick crabs and have a cold drink.

In Oxford, you’ll want to spend your days hanging out with the locals at the Oxford Social. Stop by the Oxford Museum and go for a ride on the Oxford-Bellevue Ferry! But no matter what you plan to do while exploring this cute Chesapeake Bay town, you must stop by Scottish Highland Creamery for the most delicious ice cream on the bay!

State: Maryland
Closest Major Airport: Baltimore-Washington International Airport (BWI)
Where to Stay: Robert Morris Inn or The Oxford Inn

Crisfield, Maryland

Recommended by Us!

Another town worth a visit to Chesapeake Bay is Crisfield, Maryland! This town on the bay is full of culture and history, fun things to do, and delicious blue crabs! The town is known as “The Crab Capital of the World”! It’s also not too far from Ocean City, so if you’re looking to spend some time on the ocean, that would make a great day trip!

We spent three months here during our time on America’s Great Loop, so we started to feel like locals and know so much about this cute town! Don’t expect a cute town like Oxford, but in Crisfield, you’ll get to learn about the blue-collar backbone of the Bay.

The most important thing to do in Crisfield is eat the delicious local seafood. Crisfield is arguably the best place to eat crab since it is named the crab capital, after all! We recommend The Crab Place for all-you-can-eat seafood or Waters Edge Cafe for delicious crab cakes and she crab soup.

You’ll also want to visit the Tawes Museum to learn all about the town, it’s history and crabbing! Afterward, walk down to the public pier to enjoy the waterfront views and imagine life as a waterman.

And while you’re here, we highly recommend taking a tour to some of the nearby islands like a Smith Island Cruise or a Tangier Island Cruise!

State: Maryland
Closest Major Airport: Norfolk International Airport (ORF), but Salisbury Regional Airport (SBY) is a great small airport nearby!
Where to Stay: Lady Grace Bed and Breakfast

Smith Island, Maryland

Recommended by Cecilia of Lovicarious

Smith Island is an archipelago located in the Chesapeake Bay, 10 miles off the coast of Crisfield, Maryland, and across from the mouth of the Potomac River, one of the major rivers that flows into the bay.

With a population of around 276 people, you’d be surprised to learn that there are many things to do on Smith Island, and it’s one of the best small towns on the Bay. Its marshy waterways are a kayaker’s dream. Bayside Inn Restaurant serves the freshest Maryland crabcakes you will find. The island is also home to the official Maryland state dessert, a cake featuring 8 to 15 thin layers each separated by a delicate layer of chocolate frosting.

This island in the Chesapeake is truly unique in that they have their own dialect dating back to British settlers from Cornwall, Wales, and Dorsett back in the 1700’s.  If that isn’t reason enough to visit, then the island is projected to be completely eroded by 2100 should the sea level continue to rise. Now is the time to visit this Chesapeake Bay town.

Smith Island is only accessible by boat. Smith Island Cruises provides a ferry service to the island from Crisfield, Maryland. The boat trip takes approximately 40 minutes.

State: MD
Closest Major Airport: Norfolk International Airport (ORF), but Salisbury Regional Airport (SBY) is a great small airport nearby!
Where to Stay: Smith Island Inn

Onancock, Virginia

Recommended by Us!

Onancock is a charming small town with a big heart. Although this town is a supply center for Tangier Island (the last inhabited island in Virginia), the Onancock Historic District has a lot to offer. The town has a unique collection of antique stores, galleries, gift shops, and restaurants. It’s small-town charm at its finest! Located on the southern end of the eastern peninsula on the Chesapeake Bay, visitors can travel by car coming down the eastern shore peninsula or travel north from the Chesapeake Bay Bridge Tunnel.

One of the best things to do in Onancock is to rent kayaks to explore the water. You’re bound to see watermen from the Chesapeake Bay coming in with their catches or see a variety of birds, including cranes, herons, bald eagles, falcons, hawks, or osprey on the Historic Onancock Creek. You can learn about local history at the Ker Place or the Watermen’s Museum and Research Center. Onancock also has an old-time single-screen old time movie theatre with a balcony that was built in 1950. You can feel like you’re returning in time as you see a movie at the Roseland Theatre.

One of the highlights of Onancock is The Corner Bakery, located on Main Street, which serves out-of-this-world donuts and cinnamon rolls! Head to local restaurants like Mallards on the Wharf for some delicious lump crab cakes while enjoying views of the creek, or head to The Blarney Stone Irish Pub for a pint and some traditional pub food with a Chesapeake twist.

Onancock is the sweetest little place to visit when exploring the best Chesapeake Bay towns!

State: Virginia
Closest Major Airport: Norfolk International Airport (ORF)
Where to Stay: The Inn at Onancock

St. Michaels, Maryland

Recommended by Us!

St. Michaels is the classic eastern shore Maryland town to experience the blend of the area’s history with a causally elegant lifestyle of today. You can easily get to St. Michaels by car from the mainland of Maryland or travel up the eastern shore from the Chesapeake Bay Bridge Tunnel.

The Chesapeake Bay Maritime Museum has 18 acres of waterfront attractions and interactive exhibits to share the culture of this region. The museum features a floating fleet of historic boats, 12 exhibit buildings, and several changing exhibits. It’s a true gem to the local community and visitors alike. While visiting St Michaels, take a leisurely stroll around the town center at St. Mary’s Square and enjoy the architecture of the old homes in the area. We recommend renting kayaks or a sailing tour to explore the area by water. Or take a boat ride up to nearby Rock Hall, another great option for the best Chesapeake Bay towns that are located on the mouth of the Chester River.

The Crab Claw is a popular local favorite serving fresh local crabs, oysters, and clams. It’s located on the waterfront on the Navy Pier, giving you a great view as you enjoy your meal. We loved getting some local beers at the Eastern Shore Brewery.

State: Maryland
Closest Major Airport: Baltimore-Washington International Airport (BWI)
Where to Stay: Parsonage Inn Bed and Breakfast in conveniently located in the historic district and comes with a three-course breakfast and friendly staff. Or stay at the St. Michaels Inn for a less expensive stay just a few minutes from town.

Chesapeake City, Maryland

Recommended by Us!

Chesapeake City is located on the C&D Canal, a waterway that connects the Chesapeake Bay with the Delaware Bay with a 30-mile-long man-made cut. The C&D Canal, or Delaware Canal, is one of the busiest working commercial canals in the world, and Chesapeake City is centrally located near the canal. It’s located 1 hour and 25 minutes away from Baltimore, Maryland, 45 minutes from Wilmington, Delaware, and 1 hour and 30 minutes from Philadelphia, Pennsylvania, by car, making this one of the most centrally located Chesapeake Bay towns to visit!

The town was built in the 19th century and is on the National Register of Historic Places. The best way to enjoy Chesapeake City is to walk around downtown and enjoy the beautiful architecture that still remains intact, explore the C&D Canal Museum, and learn about why the canal is so important to the United States. Lastly, stroll to Pell Gardens and watch small local and large commercial traffic navigate the canal.

We traveled here by boat, but if you’re traveling by car and want to experience the canal from the water, you can take a tour with one of the two local companies: MV Bay Breeze and Chesapeake City Water Tours. If you’re feeling up for it and inspired by the canal, then you can take the 15-mile paved Ben Cardin C&d Canal Recreation Trail, which goes to Delaware City, Delaware.

Enjoy dinner with a view at Chesapeake Inn Restaurant and Marina, which overlooks the Back Creek and has a view of the Chesapeake City Bridge. They serve a variety of seafood options, a pub fare menu on their lower level, and hand-cut steaks, fresh seafood, and pasta on their upper level. After dinner, head to Canal Creamery for a local ice cream spot with views overlooking the C&D Canal.

State: Maryland
Closest Major Airport: Philadelphia International Airport (PHL)
Where to Stay: Inn at the Canal

Cape Charles, Virginia

Recommended by Tori of Tori Pines Travels

The tiny town of Cape Charles is so quaint and beautiful and might just have some of the best things to do out of all of the Chesapeake Bay Towns. So book a few nights at the Bay Haven Inn of Cape Charles and prepare for an incredible stay!

While this town might be located on the Chesapeake Bay, not the ocean, it has a wonderful little beach to enjoy. Plus, it’s much quieter and more relaxing than the beaches nearby, like Virginia Beach, Ocean City, or Rehoboth Beach!

When in town, plan to walk along Mason Ave, the center of historic downtown, stopping in at the Cape Charles Coffee House, Coastal Baking Co., Brown Dog Ice Cream, and some of the lovely little shops along the street. To learn all about this town, its history, and its rich architectural heritage, visit the Cape Charles Museum and Visitors Center. And be sure to explore this town on foot to see the beautiful architecture and Victorian homes for yourself!

And best of all, this town is known for its fabulous golfing! Cape Charles is home to two upscale golf courses designed by Arnold Palmer and Jack Nicklaus, so a round of golf at Bay Creek is always a good idea. And for the not so avid golfers, you’re in luck because this town is home to a super cute mini golf course as well, Cape Charles Mini Golf.

Spend the afternoons on the water. Either by renting kayaks at Coastal Kayaks or going on a fishing trip on charter boats with Top Dog Charters! Either way, end your day at Cape Charles Brewing Company for a local beer!

State: Virginia
Closest Major Airport: Norfolk International Airport (ORF)
Where to Stay: Bay Haven Inn of Cape Charles

Looking for more Chesapeake Bay Towns to explore?

Here are a few other great options for towns along the Chesapeake Bay!

• Rock Hall, Maryland
• North Beach, Maryland
• Tilghman Island, Maryland
• Chesapeake Beach, Maryland
• Tangier, Virginia

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