Exploring the Eastern Shore

Maryland's Chesapeake Bay offers quaint and memorable small towns, fresh-from-the-sea crab, and lots of laid-back leisure.

Exploring the historic St. Michaels Marina.

Photo by: David Hillegas

Discover Chesapeake Bay

You could spend a lifetime exploring the Chesapeake Bay, but even if you have only a few days and can't cover its 8,000-plus miles of coastline, a brief trip to Maryland's Eastern Shore will leave you with indelible impressions. You'll find everything from posh hotels to isolated B&B's, impromptu sailboat rides to luxury cruises, down-home crab boils to four-star cuisine.

The Bartlett Pear Inn

Photo by: David Hillegas

Easton

This artsy city hosts a plein air festival every July and is chockablock with art galleries, antiques shops, and restaurants. Don't miss the Saturday farmers' market in the square.

Where to stay: Tidewater Inn, 101 E. Dover St.; 800/237-8775 or tidewaterinn.com. Bartlett Pear Inn, 28 S. Harrison St.; 410/770-3300 or bartlettpearinn.com

Oxford

Photo by: David Hillegas

Oxford

Sometimes called the Hamptons of the Chesapeake, Oxford is filled with many charming 300-year-old homes, some lining the Tred Avon River. Get there via the Oxford-Bellevue ferry, the oldest known privately owned ferry in operation in America.

Where to stay: Combsberry Inn, 4837 Evergreen Rd.; 410/226-5353 or combsberryinn.com. The Robert Morris Inn, 314 N. Morris St.; 410/226-5111 or robertmorrisinn.com

Rock Hall

Photo by: David Hillegas

Rock Hall

Sometimes referred to as "the pearl of the Chesapeake," this laid-back town is home to annual regattas, lively music, and spectacular sunsets.

Where to stay: Osprey Point Inn, Restaurant, and Marina, 20786 Rock Hall Ave.; 410/639-2194 or ospreypoint.com.

Young crabbers check their nets on a dock in the St. Michaels harbor.

Photo by: David Hillegas

St. Michaels

The most popular town on the Eastern Shore, St. Michaels has a beautiful harbor with several waterfront dining options, the Chesapeake Bay Maritime Museum, and Talbot Street, studded with more restaurants and boutiques, and a classic ice-cream shop.

Where to stay: The Inn at Perry Cabin, 308 Watkins Ln.; 866/278-9601 or perrycabin.com. Five Gables Inn & Spa, 209 N. Talbot St.; 410/745-0100 or fivegables.com.

A crabber trolling for his daily haul in the waters off Smith Island.

Photo by: David Hillegas

Smith Island

Scarcely populated, this tiny island makes for an ideal excursion if you want a nitty-gritty crabbing experience. Drum Point Market is open for lunch and dinner and is said to serve the best crab cake in the world.

Where to stay: The Inn of Silent Music, 2955 Tylerton Rd.; 410/425-3541 or innofsilentmusic.com.

Tilghman Island

Photo by: David Hillegas

Tilghman Island

This watermen's village is the largest sportfishing hub on the Chesapeake. Check out the exquisite houses on the drive from St. Michaels and the maritime relics at the Tilghman Watermen's Museum.

Where to stay: Black Walnut Point Inn, 4417 Black Walnut Point Rd.; 410/886-2452 or blackwalnutpointinn.com. The Tilghman Island Inn, 21384 Coopertown Rd.; 410/886-2141 or tilghmanislandinn.com.

These roadside restaurants provide local charm and fabulous food.

Photo by: David Hillegas

5 Dining Spots by Land

These roadside restaurants provide local charm and fabulous food.

1. 208 Talbot: 208 N. Talbot St.; St. Michaels; 410/745-3838 or 208talbot.com

2. Bistro St. Michaels: 403 S. Talbot St., St. Michaels; 410/745-9111 or bistrostmichaels.com

3. Hunters' Tavern at Tidewater Inn: 101 E. Dover St., Easton; 410/822-1300 or tidewaterinn.com 

4. Mason's: 22 S. Harrison St., Easton; 410/822-3204 or masonsgourmet.com

5. The Red Roost: 2670 Clara Rd., Whitehaven; 410/546-5443 or theredroost.com

Want to dock and dine at these hot spots? Just check the latitude and longitude.

Photo by: David Hillegas

5 Dining Spots by Sea

Want to dock and dine at these hot spots? Just check the latitude and longitude.

1. Bayard House: lat. 39°31'40", long. 75°48'44", 11 Bohemia Ave., Chesapeake City; 410/885-5040 or bayardhouse.com

2. Cheshire Crab Restaurant: lat. 39°7'37", long. 76°28'24", 1701 Poplar Ridge Rd., on Bodkin Creek, Pasadena; 410/360-2220 or cheshirecrab.com

3. The Crab Claw: lat. 38°47'12", long. 76°13'14", 304 Burns St., St. Michaels; 410/745-2900 or thecrabclaw.com

4. Drum Point Market: lat. 37°58'6", long. 76°1'22", 21162 Center St., Tylerton; 410/425-2108

5 More Waterside Dining Spots

Photo by: David Hillegas

5 More Waterside Dining Spots

6. The Masthead at Pier Street Marina: lat. 38°40'57", long. 76°10'26", 104 W. Pier St., Oxford; 410/226-5171

7. Schooner's: lat. 38°41'36", long. 76°10'5", 314 Tilghman St., Oxford; 410/226-0160 or schoonersonthecreek.com

8. Suicide Bridge Restaurant: lat. 38°37'59", long. 75°56'51", 6304 Suicide Bridge Rd., Hurlock; 410/943-4689 or suicide-bridge-restaurant.com

9. The Tilghman Island Inn: lat. 38°43'13", long. 76°20'13", 21384 Coopertown Rd., Tilghman Island; 800/866-2141 or tilghmanislandinn.com

10. Waterman's Crab House: lat. 39°7'58", long. 76°14'38", 21055 E. Sharp St., Rock Hall; 410/639-2261 or watermanscrabhouse.com

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