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Longstreet Highroad Guide to the Chesapeake Bay

By Deane Winegar

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Chesapeake Bay > The Eastern Shore: Maryland > Talbot County

Talbot County

Talbot County marks the midpoint of Maryland’s Eastern Shore, with Queen Anne’s County and the Wye East River to the north and Dorchester County and the Choptank River to the south and east.

The entire western side of the county is laced with peninsulas, coves, and inlets that are called creeks and rivers, but are really tidal estuaries where salt and fresh water mix. This topography is responsible for shaping Talbot County’s history. The protected waters of the county’s 602 miles of shoreline make fine harbors, allowing boats to penetrate far inland. Wintering waterfowl seek refuge from the weather in the same waters. Blue crabs, oysters, and clams inhabit the estuary around Talbot’s islands and peninsulas. The Choptank River is a favored spawning area for rockfish (striped bass).

The rich bounty of fish, shellfish, and waterfowl attracts anglers, hunters, and nature lovers to Talbot County. Historic villages whose residents have subsisted by harvesting and processing seafood for centuries have their own stories to tell. Ports like the ones at St. Michaels, Tilghman Island, and Oxford are synonymous with Chesapeake Bay watermen.

The acclaimed Waterfowl Festival at Easton and other bay-related celebrations also have their roots in the area’s culture. Museums such as the Chesapeake Bay Maritime Museum at St. Michaels help visitors comprehend the intimate ties between the people of the Eastern Shore and the bay. The adventurous can learn about Talbot by renting kayaks or canoes to investigate marshes that are home to herons, egrets, muskrats, beaver, and raccoons. The outdoors lovers can drop a crab line from a pier or rent a bicycle to pedal the quiet back roads.

Outfitters and guide services are ubiquitous and are available for sight-seeing, fishing, crabbing, hunting upland game or waterfowl, sailing, boating, canoeing, kayaking, and bicycling. A map of popular bicycle routes is available from the county chamber of commerce. Charter captains and cruise boats offer bay and river excursions. Several golf courses, including the plush Easton Club Golf Course on the Tred Avon River, provide another form of recreation.

The inviting aroma of Chesapeake Bay seafood drifts from harbor-side restaurants where tired wanderers relax over a glass of wine while awaiting a platter of steamed crab or grilled catfish. At the end of the day, after a satisfying meal, visitors can lay weary heads on a pillow in the Tidewater Inn at Easton, or at any of the other historic inns, waterfront inns, bed and breakfasts, and country hotels and motels of Talbot County.

Wye Oak State Park

[Fig. 19(3)] Wye Oak State Park exists to protect the largest oak tree in the United States. The Wye Oak is a white oak (Quercus alba) that is thought to be more than 450 years old. It is located on MD 662 in the community of Wye Mills, just south of the Queen Anne’s County line.

No one knows exactly what year the acorn that produced this amazing tree fell to the ground, but an educated guess is the year 1540. The tree has lived through the colonization of the Eastern Shore, the Industrial Revolution, the Civil War, and two world wars. It has weathered an untold number of thunderstorms, windstorms, and icings.

During that time, the Wye Oak grew 96 feet, its branches gradually reaching 119 feet across. A person standing beside this giant survivor is dwarfed. The massive, gnarled trunk is 31 feet and 4 inches in circumference. Some 3,500 feet of cables stretch from branch to branch for stabilization. An access hole in the trunk allows the tree’s caretakers to keep tabs on the innards, where a fungus and termites once hollowed out the tree to a height of 10 feet.

Huge growths or knees at the base of the tree have an unknown origin. Speculation includes the theory that horses were tethered under the tree while their owners visited a nearby tavern or country store. The severe bruising from the horses’ hooves may have caused the tree to produce the burls for protection.

Next to the ancient oak is a little one-room schoolhouse constructed of now faded brick. It is thought to be the oldest school in Talbot County, dating back to colonial times. Inside are a schoolmaster’s desk and a long table made of pine. A dunce stool stands in the corner, where recalcitrant students were made to sit. Many students came and went, perhaps eating their lunch in the shade of the Wye Oak, while the tree grew imperceptibly but steadfastly to its enormous size.

On the other side of the tree is the Wye Church, built in 1721, one of the oldest Episcopal churches in Talbot County. Beneath the church are the remains of an even older structure thought to have been built in the late 1600s. The building’s exterior is original. The interior has been restored to its original condition, featuring high box pews and a hanging side pulpit. The community of Wye Mills takes its name from Old Wye Mill, which has been in operation since 1664. Old grindstones still turn on weekends, making flour from grain. The same grindstones produced flour for the Continental Army during the Revolutionary War.

Pickering Creek Environmental Center

[Fig. 19(4)] The 400 acres of hardwood forests, wildlife plantings, nontidal wetlands, and nature preserve at Pickering Creek Environmental Center are a sanctuary of the Chesapeake Audubon Society. A mature forest on the property was possibly once the site of a seasonal Matapeake Indian village, although evidence is sketchy.

Pickering Creek, which flows through the environmental center, is home to northern river otters. The otters are nocturnal and not often seen by hikers or canoeists. They feed primarily on fish in addition to crayfish, crabs, frogs, and other stream life. New at the center is a list to help people identify some of the 130 species of birds that have been sighted here.

A deep-water pier attracts anglers to try for striped bass, perch, and shad. The welcome center has a reference library and educational displays. Every Talbot County child in first through sixth grades learns about protecting the environment by visiting the center or from educators at the center who visit the schools.

Visitors may hike the trails of the sanctuary. Because of high insurance costs, canoes are no longer available for rent, but may be used free of charge by members of the center who wish to explore Pickering Creek. Leashed pets are allowed on farm trails, but not on nature trails.

Easton

[Fig. 19] The tree-lined streets, old-fashioned lampposts, gift and antique shops, and historic buildings of Easton combine to give this town a charm that attracts many people to the heart of Talbot County.

The town’s interesting mix of architecture tells a story of devastating fires (1810, 1855, and 1878), wars, and the rise and fall of the railroad. The oldest religious building still in use in the United States is the Third Haven Friends Meeting House at 405 South Washington Street. Quakers constructed it in 1682 next to an old Indian trail on land that was soon to become a town. The town was first called Talbot Court House, then changed to Easton in 1788 when it became the county seat.

The amenities of the town, surrounded as it is by picturesque countryside, make it an ideal base for bicyclists. Tilghman Island and the nearby towns of St. Michaels and Oxford are perfect destinations for scenic day trips. A circuit that includes Oxford, Easton, and scenic rides on Talbot County peninsulas makes use of the Oxford-Bellevue Ferry for one leg of the trip. A certain amount of backtracking through equally beautiful countryside is required to cycle to St. Michaels and Tilghman Island from Easton and back. Bikes may be rented in Easton, Oxford, or St. Michaels.

Maps for historical walking tours of the town are available through the Historical Society of Talbot County. The three-story Federal-style brick town house at 25 South Washington Street in which the society is housed is a landmark in its own right, constructed by a Quaker in 1810. In a neighboring building in the society’s museum complex is a Talbot County history exhibit. On the grounds are Federal-style gardens, lovingly nurtured by the Talbot County Garden Club to achieve national recognition.

Another of the town’s popular attractions is the Academy of the Arts (410-822-0455), housed in a restored 1820 schoolhouse at 106 South Street. Visitors may view the works of some of America’s most famous nineteenth and twentieth century artists here.

The Avalon Theatre (410-822-0345) at 40 East Dover Street is located in a 1920 building that was once a movie and vaudeville house. The renovated Art-Deco building now boasts state-of-the-art sound and lighting, adding to Easton’s eclectic mix of past and present. Today’s theater-goers are treated to movies, plays, concerts, and other events. A small visitor center is also located here.

Even more famous than the town itself is the world-renowned Waterfowl Festival (410-822-4567), an event that raises funds for waterfowl conservation. On the second full weekend of November, some 20,000 people from across the country flood the little town of Easton about the same time hoards of ducks and geese splash down on local ponds, marshes, and rivers. The waterfowl come to spend the winter. The people come to spend three days viewing exquisite waterfowl art, to watch the world’s best decoy carvers work their magic, to hear goose- and duck-calling competitions, to marvel at the world’s best working retrievers, and to collect some of the art and decoys for their homes. Millions of dollars taken in during the festival over three decades have been put to use protecting and providing habitat for waterfowl.

No description of Easton would be complete without a mention of the elegant and gracious Tidewater Inn. Called "the pride of the Eastern Shore," the Tidewater Inn is known for its fine service, its large open fireplaces, and its eighteenth century reproduction furniture. The inn caters to fishermen and duck hunters with early morning breakfasts, guide services, and dog kenneling. It is located in the heart of town at the intersection of Harrison and Dover streets.

Holiday lighting and the month-long Dickens-of-a-Christmas Festival (410-820-9616) make Easton a magical place to celebrate December. The festival is family-oriented, complete with carriage rides and a parade.

Night life is available at several spots in town. Both the Eagle Spirits Restaurant at the Easton Club (410-820-4100) on 28449 Clubhouse Drive and the Columbia Restaurant at 28 South Washington Street are upscale eateries that offer evening entertainment. Reservations are suggested. At 42 East Dover Street is the Legal Spirits Restaurant (410-820-0033), with a lively pub near the front and a small and quieter dining area in the back. Pricing is moderate.

Casual dining is also available daily at the Washington Street Pub (410-822-9011), located across from the courthouse at 20 North Washington Street. The pub has a raw bar and 19 beers on tap. The Rustic Inn Restaurant and Tavern (410-820-8212) in a corner of TalbotTown Shopping Center has an authentic historic interior and offers fine dining. Pricing is moderate to expensive.

Choptank Wetlands Kings Creek Preserve

[Fig. 19(5)] Canoeists and kayakers who would like to combine a pretty stretch of river with a side trip into a pristine tidal marsh will want to check out Kings Creek Preserve, located off the Choptank River east of Easton. This 250-acre marsh is part of the 656-acre Choptank Wetlands, a joint venture of The Nature Conservancy and the Waterfowl Festival, Inc., for the protection of wintering and nesting waterfowl and spawning fish. Such wetlands also provide an extraordinary benefit to the Chesapeake Bay watershed by assisting in sediment control and by filtering out excess nutrients from upstream pollution. In a survey, the Smithsonian Institution found the Choptank Wetlands to be one of the most important natural areas of the Chesapeake Bay.

The remaining 406 acres of the Choptank Wetlands is the Hog Island Preserve on the Caroline County side of the Choptank, a bit farther downriver. Hog Island is not open to the public.

Kings Creek Preserve is accessible by a 0.5-mile boat trip. Access by land is occasionally permitted by prior arrangement. Those who enjoy watching birds and studying plant life from the preserve boardwalk will also enjoy paddling the undisturbed area of the Choptank and Kings Creek to get to the preserve. Blue-winged teal (Anas discors) feeding on the wild rice (Zizania aquatica), tidemarsh waterhemp (Amaranthus cannabinus), and dotted smartweed (Polygonum punctatum) in the marshy edges may take to the air ahead of canoeists. At the preserve, a 2,000-foot boardwalk leads over the brackish wetland where red-winged blackbirds flash their red epaulets from a stand of phragmites and osprey build rough nests of sticks in tall pines.

In addition to the expanses of phragmites (Phragmites australis), dominating plant species include arrow arum (Peltandra virginica), switchgrass (Panicum virgatum), and cattails (Typha latifolia). Spring and summer are good times to see flowers. Signs along the boardwalk interpret the extremely rich mix of plants and animals in this ecosystem. An elevated platform gets you above the marsh for a better view. The brochure and bird checklist available at the entrance are also a help in understanding the marsh and in identifying such species as the northern harrier (Circus cyaneus), wood duck (Aix sponsa), and common snipe (Capella gallinago). The snipe is ordinarily a solitary bird, but it migrates in a flock, usually at night. It is a popular game bird.

Seth Demonstration Forest

[Fig. 19(6)] Southeast of Easton on Dover Neck Road is Seth Demonstration Forest, a 125-acre forest of loblolly pine and hardwood trees where visitors can observe wildlife, hike, and hunt. The demonstration forests of the state’s Department of Natural Resources are set aside to help private landowners learn about wise forest management practices.

St. Michaels

[Fig. 19] This Talbot County town on MD 33 west of Easton is a destination point for many travelers because of its interesting blend of history, its small-town flavor, and its many gift shops, fine restaurants, and lodging Facilities. The streets of town are lined with homes and shops from the eighteenth and nineteenth centuries, built in Colonial, Federal, and Victorian styles.

Also, St. Mary’s Square Museum is housed in a building that was constructed in about 1800 as part of a steam and gristmill. This museum is located between Mulberry Street and East Chestnut Street on the original village green in the center of town. Brochures for the St. Michaels Walking Tour, which takes in the historic streets and the harbor, are available at the museum. Carriage rides, a tour and shuttle service, and river cruises provide additional ways to become acquainted with St. Michaels.

Newcomers to St. Michaels often ask townspeople to tell the story about how the little town fooled the British during the War of 1812. Because the important shipyards here produced privateers, blockade runners, and naval barges, the town became a target. Residents, forewarned that an attack was imminent in the early morning darkness of August 13, 1813, hoisted lanterns to the tops of trees and ship masts, causing the British to aim too high and overshoot the town. Only one house was hit, earning the name Cannonball House. The cannonball broke through the ceiling and rolled across the attic and down the stairs. A mother and her baby daughter were unhurt.

The cannon on St. Mary’s Square were used in the Revolutionary War and transported here from Sewell’s Point in Virginia. The smaller one was probably used in the defense of St. Michaels against the British in that 1813 bombardment. The bell on St. Mary’s Square is known as the Mechanics Bell, once heard daily at 7 a.m., noon, and 5 p.m., marking the passage of the day for the workers in the nearby shipyards.

In addition to its shipbuilding past, St. Michaels is known for the tough watermen whose history is told at local museums. One local business distributed a million pounds of crabmeat a year and 16,000 gallons of oysters a week to Baltimore and Philadelphia. James Michener, who lived here while writing his novel, Chesapeake, delved into the history and culture of those watermen.

St. Michaels fine inns and restaurants are legendary. Look for several of them on Green, Chestnut, Cherry, North Harbor, and North Talbot streets. One of the popular places to find night life is the piano bar at Jon and Mike’s on the Miles, located behind the St. Michaels Town Dock Marina at 125 Mulberry Street.

Chesapeake Bay Maritime Museum

[Fig. 19(7)] Many museums consist of a collection of artifacts inside a building. The Chesapeake Bay Maritime Museum at St. Michaels certainly has its share of artifacts demonstrating the close ties between the Eastern Shore and the Chesapeake Bay. The nearly 10,000 objects relate to commerce and trade, navigation, fisheries, and waterfowling. Items include working decoys by famous regional makers including Sam Barnes, Ben Dye, Daddy Holly, Ira Hudson, and the Ward brothers. There are tools used by oystermen, and relics from the War of 1812.

But this museum is more than the things inside. The structures—there are nine of them on a 16-acre site—are the museum. A bandstand on the grounds is the site for summer concerts of bluegrass, country, jazz, brass bands, and folk music. The Point Lookout fog bell tower, constructed at the mouth of the Potomac River in about 1888, is also on exhibit. The 1,000-pound bell, sounded automatically by a weight-driven machine, once helped guide boats in the bay’s notorious fog.

One of the museum’s most popular attractions is the old Hooper Strait Lighthouse, a cottage-style, screwpile lighthouse built in 1879 that has been fully restored, complete with flashing light. The lighthouse was moved to the museum site from its original location at Hooper Strait about 39 miles south of St. Michaels. Screwpile lighthouses were positioned in the water on iron pilings that were screwed into the bottom of the bay in an attempt to protect the house from damaging ice. Other historic buildings at the museum include the Eagle House, circa 1890, home of a steamboat captain, and a 1933 cannery warehouse.

The thousands of visitors who flock to the maritime museum are fascinated with the 85-vessel collection of wooden, sail, power, and row boats—the largest and most important collection of its kind in the world. The floating fleet of Chesapeake Bay workboats includes a Chesapeake Bay skipjack, a crab dredger, a river tug, a draketail, a dory boat, and a log-built bugeye. The bugeye, the Edna E. Lockwood, is a National Historic Landmark. Boats such as this one were the workhorses of the oyster industry in the late nineteenth and early twentieth century, designed with shallow draft and thick log bottoms to protect the boat from sharp oyster shells.

A small shed at the museum contains many more boats, including a dugout canoe such as those used by local Indians. Majestic tall ships, including The Pride of Baltimore II, a replica of a Baltimore clipper, regularly sail into the museum harbor.

Exhibits in the museum’s Waterfowling Building describe the sporting traditions that have built up over the years around the annual visitation of thousands of migrating ducks, geese, and swans on the Atlantic Flyway. Outside the museum is a statue of Canton, ancestor of today’s Chesapeake Bay retriever, a strong-swimming bird dog with webbed feet specifically bred for retrieving downed waterfowl.

The museum sponsors some of the Eastern Shore’s most popular festivals and shows between May and December, including such events as the Antique and Classic Boat Festival in June, Crab Days in August, the Mid-Atlantic Small Craft Festival in October, and OysterFest in November.

Nearly 100,000 people from all over the world visit the Chesapeake Bay Maritime Museum annually, helping to support this private, not-for-profit facility with entry Fees and donations.

Tilghman Island

[Fig. 19] Tilghman Island, barely over 3 miles long, is at the southern tip of a long finger of land that reaches westward into the Chesapeake Bay from Talbot County. MD 33 and a drawbridge connect it to the mainland across Knapps Narrows on the northern end. The Choptank River meets the bay at the southern end of the island.The shape of the long peninsula that is punctuated with Tilghman Island at the end is similar to the shape of Kent Island on the western side of Queen Anne’s County to the north. A major difference in topography, however, has resulted in a great difference in traffic. Kent Island was much closer to the western shore—close enough to be connected by a bridge. The northern part of Kent Island became a thoroughfare between the two sides of the Chesapeake Bay. A motorist has to go out of the way, however, to follow MD 33 for 11 miles past St. Michaels to Tilghman Island.People do go out of the way to find Tilghman, nevertheless. The island is a quiet refuge, known for its fine seafood restaurants, its bed and breakfast inns, its genteel hospitality, its sail charter opportunities, and its marshes teeming with waterfowl. Boaters love the island for its many harbors and marinas and the sport-fishing and crabbing opportunities. Tilghman Island is a fine place to become acquainted with the bay. There are narrated cruises, kayaks to rent, and sail-powered skipjacks and yachts to charter. In fact, the island is home to the largest commercial sailing fleet in the world.

From Tilghman Island’s southern tip and the end of MD 33, Sharps Island Lighthouse is visible above the water 4 miles to the southwest. This round lighthouse on a caisson foundation is not open to the public.

Charter captains across the Chesapeake Bay bring parties to the island specifically to sample the delicious seafood and prime rib served family style at Harrison’s Chesapeake House (410-886-2121). A 14-boat charter fleet, two cruise boats, and a country inn are all part of Harrison’s, which is located on Dogwood Harbor on the island’s eastern shore. Fantastic fishing makes Harrison’s and other charter operations profitable. Rockfish (striped bass), Spanish mackerel, black drum, Norfolk spot, sea trout, and croaker reward anglers for their efforts.

Night life on the waterfront is available at Harrison’s and at Tilghman Island Inn (800-866-2141 or 410-886-2141) at 21384 Coopertown Road.

Oxford

[Fig. 19] Oxford, officially founded in 1694, is one of Maryland’s oldest towns. Its location near the mouth of the Tred Avon River was important to its future as a seaport. Beginning in 1694, the province of Maryland permitted only two ports of entry to operate on the Chesapeake Bay—Annapolis (which was then called Anne Arundel) on the west coast and Oxford on the Eastern Shore. Many tobacco growers established their plantations close to Oxford. British ships engaged in a brisk trade, bringing supplies from the old country and exporting tobacco and other products.The American Revolution, however, brought the end of British shipping and the end of Oxford’s affluence. Plantations changed their operations from tobacco to wheat. Businesses went bankrupt and grass grew in the city streets. It would take nearly a century and the coming of the railroad in 1871 for the people of Oxford to find a new wealth, which lay in the oyster beds at the bottom of the Chesapeake Bay. Until the oyster beds became seriously depleted in the early 1900s, the little town flourished again.Following the decline of the oyster beds, and the consequent loss of the railroad and of steamship trade, Oxford once again became a quiet, out-of-the-way place, inhabited by a few inveterate watermen.The very somnolence of the town on the Tred Avon River is what people who live in the metropolitan areas of Baltimore and Washington, DC, are seeking. In recent years, several businesses have sprung up to provide services to tourists. There are bed and breakfast inns, restaurants, gift shops, marinas, and boat and yacht repair yards.

Yachts and sailboats are available for charter or rent at several places. Bicycles can also be rented (The Oxford Mews, 410-820-8222) to tour the streets of town and the beautiful countryside. For those who still have energy at the end of the day, night life is available. Pope’s Tavern (410-226-5220) is downstairs at the Oxford Inn at 504 South Morris Street. Latitude 38´ Bistro and Spirits (410-226-5303) is at 26342 Oxford Road. The bistro is decorated with hand-painted murals. Le Zinc (410-226-5776) at 101 Mill Street, featuring a down-home French country cuisine, offers jazz piano music in its popular bar.

At the west end of North Morris Street is the terminus for the Oxford-Bellevue Ferry (410-745-9023), which is believed to be the nation’s oldest privately operated ferry. It began its run in 1683, paused its operation from the American Revolution until 1836, and has been carrying people across the Tred Avon River to Bellevue since then. Note the Oxford Custom House here, an exact replica of an earlier customs house at the ferry terminal. The building is open on weekends from April through late fall. There is a small fee for the 10-minute ferry ride.

Relics and memorabilia from this waterfront town’s protean past are on display at the Oxford Museum at Morris and Market streets. The museum is open afternoons, Friday through Sunday, spring through fall.

Choptank River Fishing Piers State Park

[Fig. 19(8)] The Choptank River Fishing Piers State Park on the Choptank River is the innovative result of searching for a new way to use an old bridge. When the Frederick C. Malkus Bridge was constructed, the adjacent Choptank River Bridge was abandoned by automobiles and the middle of the bridge was removed. The two bridge ends were turned into piers that became the domain of fishermen, crabbers, bird watchers, and runners.The lighted piers—one extending 0.75 mile into the Choptank River from the Talbot County side, one extending 0.5 mile from the Dorchester County side—are popular places when striped bass (rockfish), yellow perch, hardheads, sea trout, and catfish are biting. Maryland blue crabs are also available in the brackish waters of the Choptank.The pier on the Talbot County side adjoins 25 acres of land that extend upriver. A path leads along the Choptank River and Bolingbroke Creek, where a walker can see spring, summer, and fall wildflowers. Rabbits, groundhogs, opossums, raccoons, and other wildlife of overgrown fields are in the area. The piers provide an excellent observation deck for watching Canada geese, osprey, and ducks.

Restaurants in Talbot County

It’s no surprise that a county with more than 600 miles of shoreline would have wonderful seafood restaurants. Here is a sampling of Talbot County’s finest:

208 Talbot. 208 North Talbot Street, St. Michaels. Lunch and dinner are served Wednesday through Sunday at this exquisite restaurant that has been named a Distinguished Restaurant of North America. Reservations are recommended. Moderate to expensive. Phone (410) 745-3838.

Crab Claw Restaurant. Navy Point, St. Michaels. Sample Maryland’s blue crabs and other Chesapeake Bay seafood while watching boats in the harbor. Open daily Mar. through mid-Dec. Inexpensive to moderate. Phone (410) 745-2900.

The Tilghman Island Inn. 21384 Coopertown Road, Tilghman. Expansive views of the Chesapeake Bay enhance the fresh seafood and American cuisine at this upscale resort inn overlooking Knapps Narrows and a waterfowl sanctuary. Winner of the Wine Spectator Award of Excellence. Live piano music is featured on weekends. Moderate to expensive. Phone (800) 866-2141 or (410) 886-2141.

Pier Street Restaurant. West Pier Street, Oxford. Dine inside or out on the waterfront at the junction of the Tred Avon and Choptank rivers at this restaurant, which is open seasonally. The menu includes fresh local seafood, steamed crabs, clams, and nonseafood items. Moderate. Phone (410) 226-5171.

Schooner’s Landing. 318 Tilghman Street, Oxford. Sample fresh seafood, steamed crabs, and Sunday brunch at this casual waterfront restaurant and bar. An outdoor deck overlooks Town Creek. Moderate. Phone (410) 226-0160.

Lodging in Talbot County

Despite the remote locations of its historic villages, Talbot County is loaded with bed and breakfasts and historic inns. Here are a few of them:

Ashby 1663 B&B. 27448 Ashby Drive, Easton. This elegant bed and breakfast has lovely waterfront views. Expensive. Phone (410) 822-4235 or (800) 458-3622.

The Inn at Perry Cabin. 308 Watkins Lane, St. Michaels. This inn features British hospitality and has been rated the fifth Best Resort Hotel in the USA. Expensive. Phone (410) 745-2200.

St. Michaels Harbour Inn and Marina. 101 North Harbor Road, St. Michaels. This harbor-front hotel has 45 luxury rooms and waterfront suites, 60 boat slips, a harbor-side pool and bar, a Jacuzzi, and a marina. Steak and seafood are on the menu at Windows, the waterfront restaurant. Pedal boats and bikes are available for rent. Expensive. Phone (800) 955-9001 or (410) 745-9001.

Wades Point Inn on the Bay. Wades Point Road, St. Michaels. This historic waterfront inn has a one-mile nature trail on a 120-acre farm. All rooms have a view of the water. Expensive. Phone (410-745-2500).

Black Walnut Point Inn. Black Walnut Road, Tilghman Island. This inn is located on a 57-acre state-owned wildlife sanctuary at the southern tip of Tilghman Island. Enjoy the views from the pool, a nature trail, the tennis courts, and from rocking chairs and bay-side hammocks. Expensive. Phone (410) 886-2452.

Chesapeake Wood Duck Inn. Gibsontown Road at Dogwood Harbor, Tilghman Island. Called "luxurious, immaculate, and well-appointed" by the New York Times, this 1890 inn has period antiques, a sunroom, and a wide lawn that stretches to water’s edge. Expensive. Phone (800) 956-2070 or (410) 886-2070.

The Moorings B&B. 7857 Tilghman Island Road, Sherwood. This comfortable inn is known for its great breakfasts and proximity to Tilghman Island. Moderate. Phone (800-316-6396 or 410-745-6396).

The Oxford Inn. 504 South Morris Street, Oxford. Located in Oxford’s historic district, this three-story B&B has traditional Eastern Shore ambiance. It has quaint, beautifully decorated rooms and a historic restaurant, Pope’s Tavern. Moderate to expensive. Phone (410) 226-5220.

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