31 Best Sights in The Eastern Shore, Maryland

Begun in 1683, the ferry may be the oldest privately owned ferry in continuous operation in the United States. It crosses the Tred Avon River between Bellevue, 7 miles south of St. Michaels (via Routes 33 and 329), and Oxford in seven to 10 minutes.

The Assateague Island National Seashore, established in 1962, occupies the northern two-thirds of a 37-mi-long barrier island, encompassing a small portion operated as Assateague State Park. ("Assateague" means "a marshy place across.") Although most famous for the small, shaggy, wild horses (adamantly called "ponies" by the public) that roam freely along the beaches and roads, this stunning island is also worth getting to know for its wildland, wildlife (including the beautiful sika deer), and for simply enjoying a pristine ocean-side environment. In summer the seashore's mild surf is where you can find shorebirds tracing the lapping waves back down the beach. There are three self-guided nature trails behind the dunes that encourage exploration of the island's forests and bay-side marshes.

Driving is permitted the length of—and several miles south of—the state park. Appropriate off-road vehicles with special permits may drive the length of the National Seashore as far as the Maryland-Virginia line. Remember that the animals here are wild, and follow the signs about not feeding or trying to pet the horses (or ponies).

Swimming, biking, hiking, surf fishing, picnicking, and camping are all available on the island. The visitor center at the entrance to the park has aquariums and hands-on exhibits about the seashore's birds and ocean creatures as well as the famous ponies.

At the tip of the Eastern Neck peninsula, 8 mi south of Rock Hall, and at the mouth of the Chester River, this 2,285-acre park is superb. It's a prime place to spot migratory waterfowl, wild turkeys, Delmarva fox squirrels, and southern bald eagles, undeterred by the experimental power-generating solar panels and wind turbines installed nearby. Nearly 6 mi of roads and trails and an observation tower provide excellent vantage points.

The largest nesting bald eagle population north of Florida makes Blackwater its home. You can often see the birds perching on the lifeless tree trunks that poke from the wetlands here, part of nearly 28,000 acres of woods, open water, marsh, and farmland. In fall and spring, some 35,000 Canada and snow geese pass through in their familiar V formations to and from their winter home, joining more than 15,000 ducks. The rest of the year, residents include endangered species such as peregrine falcons and silver-hair Delmarva fox squirrels. Great blue heron stand like sentinels while ospreys dive for meals and tundra swans preen endlessly. By car or bike you can follow a 5-mi road through several habitats or follow a network of trails on foot. Exhibits and films in the visitor center provide background and insight.

Originally the Hotel Cecil, this market became Cramer's 5&10, an old-fashioned variety store operated by a pair of proprietors who themselves became historic treasures. The building's enterprising current owner created an antiques mart, but fully restored the building's exterior and retained its well-worn wood flooring, candy jars, and display counters. You could spend a weekend here!

This nice local museum houses a permanent collection of fine art by such American artists as James McNeil Whistler, Grant Wood, Lichtenstein, and Rauschenberg, as well as Chagall and Dürer. Special exhibitions often cover local artists, and the juried art show held here in early October is one of the finest in the region.

One of the region's finest, this nine-building complex chronicles the Bay's rich history of boatbuilding, commercial fishing, navigating, and hunting in compelling detail. Exhibits on the 18-acre waterfront site include two of the Bay's unique skipjacks among the museum's more than 80 historic regional boats. There are also the restored 1879 Hooper Strait Lighthouse, a working boatyard, and a "waterman's wharf" with shanties plus oystering and crabbing tools. In the Bay Building you can see a crabbing skiff as well as a dugout canoe hewn by Native Americans. The Waterfowl Building contains carved decoys and stuffed birds, including wood ducks, mallards, and swans.

Completed in 1809 this is a glimpse into middle-class life of the early 19th century. The two-story cottage, furnished with period pieces, sits in a little yard surrounded by a picket fence.

You can often watch the crafting of oak baskets by hand, done here since 1876. Skilled craftspeople and weavers use techniques passed down through the generations.

About a 10-minute drive east of Chestertown is a Maryland Eastern Shore institution—with much more than just furniture (although there are literally a couple of acres of that). Hundreds of pieces, "other people's junk" and real treasures, are sold out in the open, regardless of the weather. A huge shed houses smaller items defying easy description, from atlases to zithers. The auction is held every Wednesday of the year (Christmas week excepted) beginning at 8 am.

Jacob Fussell began a wholesale ice-cream business in Baltimore in 1851, the first in the United States. Today privately owned and operated ice-cream parlors abound along Maryland's Eastern Shore, but Dumser's Dairyland, established in 1939, is the choice for longtime beachgoers; its vast "factory" and parlor are open from noon to midnight in the summertime. In addition to its main South Atlantic Avenue outfit, it also operates branch locations at 49th Street and Coastal and 124th Street and Coastal, as well as three smaller outlets on the boardwalk.

Believed to have been first settle on the Choptank Native American trail in the 1660s, the East New Market contains some 75 buildings of historic significance—churches, schools, businesses, and residences—representing three centuries. In this living museum of architecture, every exhibit is in its original location. An illustrated walking-tour map is available from the Dorchester County Tourism office.

About 6 mi south of the town of North East, this park juts into the headwaters of the Chesapeake Bay to its west, with the Elk River flowing along its eastern flank. You can drive almost the length of the peninsula and then walk about a mile through pleasant woodlands to the cliffs on its tip. There you can find the sparkling-white Turkey Point Lighthouse, albeit no longer in use. The 270-plus-degree view from Turkey Point is stunning. Campsites are available here, as are some charming 1950s-era wooden cabins that are admirably well maintained. Elk Neck is a prime location for picnicking as well as for fishing and swimming off sandy beaches.

home of the Historical Society of Kent County, is a splendid Federal-style home containing 18th-century furniture and an impressive teapot collection, a historical library, and a shop. It's a good place to begin a visit to Chestertown.

The Society maintains a small museum of local history and manages Tharpe Antiques. Housed in a three-story Federal brick house restored by a Quaker cabinetmaker in 1810, the society also operates Three Centuries Tours, a one-hour overview of authentically furnished homes of the 17th through 19th centuries.

There is not a lot to do in town, but to learn about its history, stop by this center operated by the Crisfield Heritage Foundation. Guided tours of Crisfield are run from here; from May through October the tours include a visit to a crab processing plant.

Headquarters to the Dorchester County Historical Society, this property houses two historic homes. The three-story, 18th-century Georgian Meredith House is rich with Chippendale, Hepplewhite, and Sheraton period antiques, and the Children's Room holds an impressive doll collection, cradles, miniature china, and baby carriages. Portraits and effects of seven former Maryland governors from Dorchester County adorn the Governor's Room. In the Neild Museum are agricultural, maritime, and Native American artifacts. There's also a restored smokehouse, blacksmith's shop, and medicinal herb garden on the grounds. Fall is ablaze with vibrant leaves and many family activities.

This attraction on the southernmost tip of the island traces the resort to its days as a tiny fishing village in the late 1800s. Housed in an 1891 building that once held the U.S. Lifesaving Service and the Coast Guard, the museum's exhibits include models of the grand old hotels, artifacts from shipwrecks, boat models, five saltwater aquariums, an exhibit of sands from around the world, and even itchy wool swimsuits and an old mechanical laughing lady from the boardwalk. Press the button, and you can be laughing with her.

Seven miles southwest of Cambridge stands this tiny church that was built around 1675. In the churchyard are the graves of four governors of Maryland and several members of the distinguished political and clerical Carroll family. Services are still held here every Sunday at 11. Extensively altered in the 1800s, the church has been restored to its 17th-century appearance.

View displays, models, and pictures of sailboats. Some boats were built in Oxford, site of one of the first Chesapeake regattas (1860). Check out the full-scale racing boat by the door. Other artifacts include the lamp from a lighthouse on nearby Benoni Point, a sailmaker's bench, and an oyster-shucking stall. Docents elaborate on the exhibits, which set the context for a walking tour of nearby blocks.

This 65-foot steel-hull yacht departs four times daily, from March through September, for one-hour cruises on the Miles River. The tour covers the ecology and history of the area as it passes along the tranquil riverfront landscape.

Stop by a venerable general store across from the ferry dock that serves excellent fresh seafood.

Started in 1996 by 12 gutsy Smith Island women, this co-op produces the finest, shell-less-quality crabmeat, with all proceeds going straight back to the women and their families. Visitors can drop by and see the lightning-fast pickers at work. Don't forget to pick up a pound before you leave, and ask Janice (the founder and president) about her secret crab-cake ingredient.

Don't skip the area's nationally known cakes—stacked eight to 10 layers high and frosted—and recently designated Maryland's state cake by lawmakers. (They can be purchased in person or online.)

From the early 1900s, this was the western terminus of the old Queen Anne's Railroad Company system.

This reproduction of a 1768 Colonial schooner by the same name was launched in 2001. With a length of 97 feet, the original Sultana was the smallest schooner ever registered on the Royal Navy Lists. The modern mission of this "Schoolship of the Chesapeake" is to provide unique, hands-on educational experiences in Colonial history and environmental science. Several two-hour public sails are available each month from April through November. Daylong public sails are scheduled on occasion. The Sultana can be seen close-up when she is anchored in the Chester River, at the end of Cannon Street. Additionally, half-day guided paddle tours operated by Sultana management are also available a few times a year in various Kent Count rivers.

The gathering point for citizens who protested the Stamp Act in 1765 and where people rallied to adopt the Talbot Resolves, this 1712 courthouse was a forerunner of the Declaration of Independence. The courthouse was expanded in 1794 and two wings were added in the late 1950s. It is still in use.

At the south end of the boardwalk, this thrill center has a "boomerang" roller coaster; the rickety and terrifying "Zipper" wood coaster; and the Hirschell Spellman Carousel, from 1902. The park has been owned by the Trimper family since it opened in 1890.

The two spacious buildings here, at the head of the North East River, preserve the rich heritage of both the commercial and recreational hunter. This unusual museum houses an extensive collection of boating, fishing, and hunting artifacts native to the Upper Chesapeake Bay: sleek sculling oars, rare working decoys, and the outlawed "punt" gun and "gunning" rigs.

Operated in partnership with Salisbury University, the Ward Museum of Wildfowl Art presents realistic marshland and wildfowl displays. Two brothers from Crisfield, Lem and Steve Ward, helped transform decoy making from just a utilitarian pursuit to an art form; their re-created studio is a must-see exhibit. Besides the premier collection of wildfowl art, the 30,000-square-foot museum has some 2,000 other artifacts as well as a gift shop and library.