Eastern Shore Towns of the Chesapeake Bay

An insider’s guide on what’s there

Day trip it!
Residents of Smith and Tangier islands still speak in the style of their European ancestors who arrived 300 years ago. Chestertown celebrates the days of tall ships. Poplar Island has been painstakingly recreated. While St. Michaels and Chesapeake City are often on “Top Ten” lists of places to visit in the United States.
All are on the “Eastern Shore.”
The numbers for these Chesapeake Bay towns are not any sort of ranking.

#1 Chesapeake City

Chesapeake City is on the canal between the Chesapeake Bay and Delaware Bay. Much of the historic village has been restored to its turn-of-the century start, but with boutiques, restaurants and B&Bs. Huge cargo ships & luxury yachts continually motor by the downtown making a very impressive view and a must-stop for boaters. All that water traffic makes some rocking marina bars — as in rollicking-fun type of rocking.


#2 Fredericktown, Georgetown & Galena

This trio of towns are close to each other. Fredericktown and Galena are on opposite shores of the beautiful Sassafras River. Both are marina villages popular with boaters for their bar scene and restaurants with gorgeous water views. The War of 1812 paused briefly here. Nearby Galena is within easy cycling distance and has antique stores and a couple markets. 


#3 Betterton

Betterton is a tiny town with a big beach that has amazing views of the Chesapeake Bay. The town is on top of a big Chesapeake Bay cliff and the beach is located below. Don’t worry, there’s a parking lot on the beach level. It used to be a major Victorian resort when people travelled via water. To get there now, you’ll venture deep into farm country, but it’s worth the ride if you like adventure. But be aware, there’s literally only a couple restaurants and not much else other than that big, beautiful beach. 


#4 Chestertown

Chestertown is a hip small-town. It’s a college town, but the private liberal arts Washington College is about a mile away from downtown, up a hill with the Victorian mansions. Down by the Chester River are the Colonial mansions taken over and beautifully rehabbed by the college. The lively downtown has Victorian park square with about the coolest, ugly cast-iron fountain in the middle.

The town has a vibrant artist colony and the downtown contains a number of high-end studios featuring jewelry to furniture. And throughout the year, Chestertown hosts festivals that take over the town. Chestertown is the port of the Sultana, a reproduction schooner that regularly offers sails to the public.


#5 Tolchester Beach

Tolchester used to be a major Victorian beach community. It’s long gone and it’s not really a town anymore. Just a marina really. But it’s still a great stop for a getaway. The marina rebuilt its beachfront into a large tiki-bar/restaurant with bands on the weekends. The long, sandy beach is on the Chesapeake Bay. Boaters raft up just outside the roped-off swimming area and dingy or swim to shore.


#6 Rock Hall

There’s not much in Rock Hall. The quiet is what the locals love about it. The town beach, 1.5 miles from downtown, faces Baltimore across the Chesapeake Bay. Rock Hall is very much a boaters’ village with marinas lining much of the water’s edge and two large bars/restaurants featuring crabs and local seafood.

Several of these marinas are setup for motorists and have inns or B&Bs, pools and very nice restaurants. The town hosts several major events every year, the biggest is Pirates and Wenches Weekend when Rock Hall is packed with visitors dressed as pirates and greeting each other with “Argh!”


#7 Kent Island/Stevensville

Long, narrow Kent Island is an often overlooked exit off of Highway 50 on the way to the Atlantic shore. Annapolis residents see Kent Island as great a weekend getaway. There’s little historic Stevensville with antique shops in the former stores that catered to island watermen and farmers.

The island has county parks with beautiful beaches and a popular, paved hiking/biking path going from one end of the island, winding along the water in sections. But it’s really known for Kent Narrows, a tight boating channel with big crab houses and bars lining both sides. The Narrows turns into a party scene during the summer.


#8 Easton

Colonial Easton has a curious combination of shops and restaurants targeting the wealthy and the working man, side-by-side. It’s ranked one of the richest small towns in the U.S. That’s due to the waterfront mansions stationed along the Chesapeake Bay for the views, the boating and the waterfowl hunting.

The town has an unusually large and stylish, small-town art museum at the corner of several historic neighborhoods. Every year, Easton hosts a huge Fall waterfowl arts-and-hunting festival which takes days to see all the artists and vendors scattered throughout town.


#9 St. Michaels

St. Michaels is a great day trip or weekend getaway. The downtown is a shopper’s boutique paradise. The harbor is a couple blocks away from downtown, but that walk gets you to restaurants along the water.

Clustered at one end of downtown are a winery tasting room, brewery and a distillery (famous for its rum). On the opposite end of town is the Chesapeake Bay Maritime Museum. It takes hours to walk through, with historic boat builders’ shops, waterman shanty and Chesapeake Bay lighthouse. A tour boat there takes visitors on water tours down the scenic Miles River where dolphins are often spotted.


#10 Popular Island

Popular Island is fascinating day trip, if you can catch a tour. The island was nearly eroded away by time and tides when Maryland decided to recreate it using fill dredged from the Chesapeake Bay channels. It’s being turned into a waterfowl sanctuary, with different sections made to attract a different type of bird. You get there only on a state Transportation Dept. boat with a tour guide. Find out about tours online.


#11 Tilghman Island

Tilghman Island is as close as you can get to the center of the Chesapeake Bay by car. The island really does stick into the middle of the bay and is an incredible migration stop for butterflies and assorted birds. That’s about as exciting as it gets on Tilghman.

Islanders are just fine with that. The island is a getaway for some of the rich and famous, which got the general store offering weekly wine tastings which attracted the working watermen just off the Bay. That’s how it goes there. A couple nice hotels are tucked off the main road, and the tiny city center has a very popular restaurant offering serious foodie cuisine, including seven-layer cake.


#12 Oxford

Oxford is the real-life version of a small town from a Hallmark Channel movie. It’s so darn adorable. White picket fences border many of the homes along the main street. The big restaurant/inn in town is in a Colonial manor. There’s a long beautiful town beach and a city park that looks like a Victorian painting.

What to do there? Oh well, there’s boating, cycling, hiking, beaching. A ferry goes across the Tred Avon river connecting the town — a short drive, or longer cycle, away — with historic St. Michaels home of the partying bars, restaurants and shopping, and Easton with the big box stores for supplies.


#13 Cambridge

Cambridge is on the beautiful Choptank River where it enters the Chesapeake Bay. The waterfront is gorgeous, which is why Hyatt built a big resort/spa there. You can go cheaper and more adventurous by going into town.

The downtown is from the Mad Men era. Buildings have been preserved and it’s now home to RAR Brewery and several restaurants. Not all buildings have tenants, yet, but it’s still a cool downtown.

The antislavery activist and Civil War spy Harriet Tubman was from the Cambridge area. The Tubman visitor center is in nearby Blackwater Wildlife Refuge, which is great for cycling or a leisurely drive. There’s also walking trails through the marshland.


#14 Crisfield

Crisfield is the town that used to be somebody. Mainly a seafood canning center for the country. Now, it’s a party stop for Chesapeake Bay boaters and where the rest of us catch a ferry to visit Smith Island and Tangier Island. Those boaters have created some fun marina bars and crab houses (that’s what they call a seafood restaurant). The town also has a really nice public beach.


#15 Smith Island

Smith Island is featured in all sorts of news stories about climate change and disappearing culture. The island is barely above sea level, but the islanders are hanging on. Many families have lived there for generations and still talk in a Colonial-Welsh manner that’s tough to understand. They speak ‘American’ when tourists are around.

You get to Smith Island only by boat. Ferries out of Crisfield will take you there for a few hours or overnight.

The. Best. Maryland-crab cakes — and seven-layer cakes — are found on Smith Island. But the island is closed to outsiders for now.


#16 Tangier Island

Tangier Island has a bigger town than Smith Island, but the culture and style are similar. Everything is within walking distance, but if you’re there just for a day it’s best to rent a bike or golf cart to be able to see more. Both islands have interesting museums and great restaurants.

If you’re wondering which to visit, take whichever one you can get a ferry ticket for. And once there, go to any restaurant that has an empty seat. They’re all good. But like Smith, Tangier Island isn’t taking visitors yet.


#17 Hooper Island

Hooper Island is series of barrier islands between the Honga River next to the mainland and the Chesapeake Bay. But unlike Smith and Tangier islands, you can get there by car. The Hooper Island road takes you across the bridge to the main island and across causeway bridges to the next two islands. There are only a couple restaurants there, and an island market. It’s a beautiful bike ride. Motorcyclists love it.


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