Talbot County, Maryland
Talbot County Website
Chamber of Commerce
Talbot County Schools
Talbot County is the place to be on Maryland’s Eastern Shore. 259 square miles of beautiful land adjoin five rivers and pristine shore line. The area strikes a perfect balance of nature and urban development, offering fine restaurants, shopping, concerts with boating, fishing and other outdoor activities. Gorgeous 18th- and 19th-Century estates are highlights of the real estate market here, but there are plenty of new developments and historic homes.
The Town of Easton is a small arts community, about 10 square miles in size. It’s home to the famous Avalon Theatre and the beautiful Tidewater Inn. The town hosts popular festivals like Waterfowl Festival (November), Festival of Trees (November and December) and the Plen Air art festival and competition (July).
Easton is known for fine dining and great local shopping. The real estate market in Easton offers a wide variety of homes for people of all tastes and means. The downtown area is known primarily for stately historic homes. There are plenty of subdivisions, like Easton Club, Easton Village and Cooke’s Hope, with new and recent construction single-family and town homes. Fine estate homes are found on Easton’s plentiful waterfront, mainly along Oxford and St. Michaels roads.
The Town of Oxford is a quiet small community on the Tred Avon River. It’s home to the Oxford-Bellevue Ferry, the famous Robert Morris Inn and the Scottish Highland Creamery, which serves the best ice cream on the East Coast. The town’s sleepy streets are lined with brick sidewalks. There’s a waterside community park, a small town grocery store and a few restaurants for good sea fare. The town itself is a narrow peninsula surrounded by water.
Oxford is known more for its marinas and its beautiful homes than for tourist attractions. Homes downtown vary in price, but they are mostly historic, colonial-style homes. The waterfront homes are particularly prized. There are also fine estate properties close to town along Oxford Road.
St. Michaels is a maritime village built around the famous St. Michaels harbor. It offers a very different lifestyle than that of neighboring Easton and Oxford. St. Michaels is a tourist destination, full of great shops and restaurants. On weekends and summer afternoons, the streets of downtown are full of locals and visitors, looking for the blue crabs and ice cream in town. A few popular destinations are the Chesapeake Bay Maritime Museum (pictured here), the Crab Claw Restaurant and The Inn at Perry Cabin. People come to town for Carpenter Street Cart Races (St. Patrick’s Day), WineFest (spring), the antique and classic boat festival (summer) and Christmas in St. Michaels.
Real estate in the area consists mostly of historic houses in town and waterfront estates just outside of St. Michaels proper. There are a few upscale developments, like Martingham and Perry Cabin, plus some more modest developments like Back Creek Landing.
Tilghman Island is best described as an "old fashioned waterman’s community." It is located on the westernmost tip of the county, and it is a popular place to live for those involved in the seafood business. It’s also a popular destination for those interested in fishing trips and other water adventures. Many people choose to buy a second home in Tilghman because of the privacy and fantastic Chesapeake Bay views found on the island.
Dorchester County, Maryland
Dorchester County Website
Chamber of Commerce
Golf in Dorchester County
Dorchester County was established in 1669, and from that time until today it has been known as a place with an abundance of fish and crustaceans, large forests and agricultural possibilities.
This is the largest county in Maryland (including its water area) containing 688 square miles and approximately 1,700 miles of shoreline. It is situated in the “heart” of the Eastern Shore with Talbot and Caroline counties to the north, Wicomico County and Delaware to the east, and the Chesapeake Bay to the west and south. The 122,000 acres of wetlands in the county make up 40 percent of the total wetlands in Maryland. These wetlands are an important part of the “life source” of the bay and have protected federal and state reserves for nature enthusiasts as well as gunning areas for the sportsmen.
Because of the large size of Dorchester County there is a diverse collection of unique communities: quaint fishing communities such as Hooper’s and Taylor’s islands to the south and west, with crab picking facilities and hunting lodges; small towns like Hurlock, East New Market and Vienna in the northern area, surrounded by agricultural grain farms, market crops, truck farms and poultry growing; and Cambridge, a city in the center of the county. It is the county seat and largest community.
Being a resident of Dorchester means always having something to do. IRONMAN Maryland takes place in September, with athletes from all over the world gathering in Cambridge to compete for a place that will send them to Hawaii in October for the big race. A major stop on the Atlantic flyway, Dorchester hosts over 250 species of birds and is home to Blackwater National Widelife Refuge, a paradise for people into birding, paddling, nature walks and cycling. The Chesapeake Bay is a one-of-a-kind body of water offering some of the best fishing and boating in the country.
As the county seat, Cambridge is the most populated area of the county. Its downtown area is going through a revitalization phase, and many new subdivisions are being built on the outskirts of town. There is also a new resort in Cambridge: the Hyatt Regency Chesapeake Bay, including a golf club and community.
Travelers with everything from skipjacks to hydroplanes make it a point to stop in Cambridge, where, for the past 103 years, the city has hosted the Cambridge Classic, a boat race on the Choptank River. For the golfers in the family there are two 18 hole courses: River Marsh at the Hyatt resort and Clearview at Horn’s Point. Then we have the Cambridge-Dorchester airport, sited on 354 acres, with a 20-foot elevation.
In the historic district of Cambridge exists one of the largest collection of vintage Victorian homes of any community on the Delmarva Peninsula. This is a waterfront city with a busy harbor, lots of restaurants and interesting historic sites to visit. A growing artist district is making life that much more interesting.
Some popular destinations are the fishing bridge, Sailwinds Park, the Cambridge Yacht Club, and the Cambridge Municipal Yacht Basin. Try to time your visit to see the Power Boat Regatta, usually at the end of July.
Caroline County, Maryland
Caroline County Website
Chamber of Commerce
Caroline County Schools
Known as the 'Green Garden County,' Caroline is mostly rural area between the Choptank River and the Mason-Dixon line. It depends heavily on agriculture, the base of its economy for 300 years. The area is growing though, with new commercial and residential developments built for families.
Denton is a small town poised on a hill that overlooks the Choptank River. Since the town’s founding in 1781, the town’s Courthouse Green has been the site of eloquent balls, circuses, baseball games, military parades, hangings, jailbreaks, and fistfights. Errant fireworks celebrating the end of the Civil War nearly destroyed the downtown on July 4, 1865. Today the annual Caroline Summerfest is held on the streets surrounding the courthouse in August.
Outside of town, there’s the fantastic Martinak State Park and great golfing at Caroline Country Club.
Queen Anne's County, Maryland
Queen Annes County Website
Queen Annes County Public Schools
Queen Anne’s County is gateway to Eastern Shore. It is one of the oldest sites of colonial settlement in the nation. The county thrives on agriculture and water industry. It is populated by small towns that welcome tourists and shoppers, as well as those interested in in touring lovingly restored historic sites.
Kent Island, full of restaurants and marinas, is a popular stop for visitors (It’s the first place you see when you get off the Bay Bridge!). Centreville is the county seat. One of the benefits of living in Queen Anne’s County is having the easiest access, on the Eastern Shore, to Annapolis, Baltimore and Washington, D.C.
Kent County, Maryland
County of Kent Website
Chamber of Commerce
Kent County Public Schools
Kent County was founded in 1642 and became established as a hub for trade in the Chesapeake Bay region, eventually becoming a major contributor towards American efforts in the Revolutionary War and the War of 1812. The county currently has several buildings in the National Register of Historic Places.
A scenic peninsula, on Maryland’s Upper Eastern Shore of the Chesapeake Bay, the County of Kent is less than a two-hour drive from Philadelphia, Washington D.C., Annapolis and Northern Virginia.
Quaint waterfront towns, including Historic Chestertown, Rock Hall, Galena, Betterton and Millington, offer sunset cruise charters, small beaches, kayaking, fishing charters, boating, sailing, museums, theaters, art galleries, brick sidewalk shopping, antiquing, farmers’ and Artisans market, local seafood, including the Chesapeake Bay Blue Crab, Maryland’s second largest collection of 18th century structures and more.
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