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A Maryland Road Trip With a Split Personality

Experience the bustling and tranquil sides of this state bisected by the Chesapeake Bay

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Discover the two faces of Maryland on this four-day road trip that takes you on opposite sides of the Chesapeake Bay, the country’s largest estuary with a watershed that encompasses six states and the District of Columbia.

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An appealing urban vibe permeates the bay’s Western Shore, where Maryland’s small but bustling capital charms with the grandeur of a military academy and a scenic harbor awash with sailboats. Cross the Chesapeake Bay Bridge to the Delmarva Peninsula, which Maryland shares with Delaware and a slice of Virginia, and the vibe shifts dramatically. Here, on the Eastern Shore, the pace slows, and Maryland’s inviting rural side unveils itself. Think pastoral landscapes, marshes harboring waterfowl, and waters rich with oysters, crab and rockfish. Historic waterman communities still thrive, and the inspiring story of a Black heroine from pre-Civil War days unfolds.

You get a beach day on the Atlantic, too, and plenty of opportunities to indulge in fresh seafood and crab feasts along the way.

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Day 1: Annapolis

​Start your adventure in the sailing haven of Annapolis, home to the U.S. Naval Academy (USNA) and Maryland’s capital. Brick-paved streets lined with vintage storefronts and 18th century brick houses give this bayside city of 41,000 people all kinds of charm. 

Begin with a walking tour of the USNA downtown for a peek at a midshipman’s life. See the nautical-themed stained-glass windows at the Naval Academy Chapel, the crypt of hero John Paul Jones, lauded as the father of the U.S. Navy, and more. Ninety-minute tours depart from the Armel-Leftwich Visitor Center hourly from 10 a.m. to 3 p.m. Monday-Saturday and from 11 a.m. to 3 p.m. Sundays. Also on campus, don’t miss the Gallery of Ships at the Naval Academy Museum, which has an impressive collection of warship models from the 17th, 18th and 19th centuries. Tour information with enhanced braille descriptions of the grounds is available on loan from the visitor center.

Less than a mile away, the Maryland State House dates to 1779, making it the country’s oldest statehouse still in continual use. Look up to discover the most notable architectural feature of this handsome Georgian structure: the wooden dome, constructed in 1794 without nails; wooden pegs reinforced by iron straps hold it together.

On lively Main Street, a few blocks south, lovingly preserved buildings from four centuries house restaurants, bars, galleries and shops for every budget. At Local by Design, you can buy everything from inexpensive decorative pottery to pricier fine art, all created by local artisans. Kitschy shops sell affordable souvenirs. Annapolis Ice Cream Company is a must-stop for a tasty treat, especially if you’re traveling with the grandkids; it has been voted the town’s best ice cream for 18 years straight.

As the sun sets, embrace locals’ favorite pastime: sailing. Take in unparalleled views of Annapolis from aboard the 74-foot Schooner Woodwind on a two-hour Chesapeake Bay sail. Feel the cool breeze in your hair as you smell the salt-tinged aroma of the water. But the schooner isn’t wheelchair-friendly, so a better option might be one of the 40-minute sightseeing cruises offered by Watermark on bigger boats with wider gangway ramps and level entrances. 

For dinner, indulge in the bay’s bounty at Boatyard Bar & Grill, a favorite of local sailors across the harbor from downtown in the Eastport district. Try the Open Faced Crab Dip Samich, made with Maryland lump blue crab. The seafood served up in restaurants on this coast isn’t necessarily cheap, but it’s guaranteed to be fresh. Try local merchants in and around the bay area for inexpensive options. 

Where to stay: Give a nod to the USNA by booking the moderately priced Graduate Annapolis Hotel downtown, about a mile west of the campus. To celebrate the Navy (and the city’s close ties to the water), the property features a nautical theme, and its 215 rooms are decorated in blue and gold, the official Navy colors. ADA-compliant rooms have extra space in bathrooms, closed-caption TVs and audible alarms.

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Day 2: Annapolis to Easton (41 miles)

​Fuel up before leaving Annapolis at Chick & Ruth’s deli, a Main Street icon serving hearty breakfast fare such as crab omelets. Time your visit to coincide with a daily reciting of the Pledge of Allegiance (8:30 a.m. weekdays, 9:30 a.m. weekends), a restaurant tradition for more than 30 years.

Now, it’s on to the Eastern Shore, via the dual-span Chesapeake Bay Bridge, also known as William Preston Lane Jr. Memorial (Bay) Bridge (toll: $4 to $6), which stretches for 4.3 miles and juts 186 feet into the sky at its highest point as panoramic views of the broad watery expanse spill out before you. Its length and height aren’t the only reasons it makes many drivers uneasy; traffic can be heavy, especially on summer weekends, guardrails are low, and morning fog sometimes limits visibility. Proceed carefully, or leave the driving to someone else. For $40 cash, Kent Island Express will send a professional driver to drive you and your vehicle across the bridge.

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The reward for making the crossing is big: Cityscapes and traffic give way to pastoral landscapes dotted with barns, cornfields and roadside markets. 

In Easton, 18th century Colonial and 19th century Victorian architecture combine with an art-centric vibe to create a delightfully endearing small town with art galleries, eateries and shops lining quaint downtown streets. A standout shop: the high-end Vintage Books and Fine Art, featuring antique maps, creations by Eastern Shore artists and rare books. 

Spend the afternoon at the Academy Art Museum, which has rotating exhibits from an impressive collection of works from the 17th century to the present, including must-see pieces by Pablo Picasso, Rembrandt van Rijn and Ansel Adams.

For a fun evening, take in a live show in the art deco Avalon Theatre. 

Where to stay: Three of the 85 rooms at the moderately priced Tidewater Inn downtown are ADA-compliant with extra space for wheelchairs and roll-in showers. For dinner, dine onsite at Hunters’ Tavern on tasty dishes such as blackened diver scallops.

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Day 3: Easton to Cambridge (37 miles)

​Drive 27 miles on U.S. Highway 50 and Maryland Routes 16 and 335 to the Harriet Tubman Underground Railroad National Historical Park in Church Creek. Born and enslaved in this area, Tubman escaped to freedom in the North, but she repeatedly risked her life by returning here in the 1850s to guide other slaves to freedom on this railroad. Learn about her bravery in the park’s visitor center via exhibits, a film and a library. Outside, meditate and reflect in its peaceful legacy garden, where you may see bluebirds, butterflies, dragonflies and even bald eagles.

For more serious birdwatching, the Blackwater National Wildlife Refuge borders the park. More than 30,000 acres of forest, marsh and shallow waterways attract migratory waterfowl, including Canada geese. Bring binoculars to spot winged creatures and other wildlife — including muskrat and white-tailed deer — along a 3.6-mile drive. 

Head 10 miles north to Cambridge, a seaport community on the Choptank River dating to 1684. Author James Michener reportedly declared High Street, lined with stately homes from the 1700s and 1800s, one of the most beautiful streets in America. Also downtown, delve more into Tubman’s life at the Harriet Tubman Museum and Educational Center. A mile away, at a memorial garden, view murals depicting her life story painted by her great-great-great nephew Charles Ross. At the Richardson Maritime Museum’s Ruark Boatworks on the eastern side of Cambridge Creek, watch volunteer boatwrights restore and build traditional wooden vessels (Mondays, Wednesdays and Fridays from 11 a.m. to 2 p.m.).

Dine at Portside on fresh seafood while watching watermen return with today’s catch. The Crab Cake entrée (broiled or fried) blends Maryland backfin and lump crab, tossed in the house sauce. 

Where to stay: Period furnishings give the moderately priced Cambridge House Bed & Breakfast, an 1847 sea captain’s manor downtown, a cozy feel. Two of its six rooms are on the ground floor, but guests must walk up a few steps to enter the property. For wheelchair accessibility, a better option is the budget-friendly Holiday Inn Express, about a mile east of downtown. 

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Day 4: Cambridge to Ocean City (62 miles)

Take Highway 50 to Ocean City, Maryland’s famed beach town, for some R&R on the Atlantic. Strolling its accessible boardwalk, which stretches for nearly 3 miles along the waterfront, is a must-do (although very crowded in the summer). It’s flanked by souvenir shops, restaurants and the quirky Ocean Gallery, which offers a mix of fine art, photographs and posters at a variety of prices. For golfers, the area has 17 courses, such as Eagle’s Landing, with lovely views of Sinepuxent Bay and Assateague Island.

If Ocean City is a bit too busy for you, venture about 10 miles south on Maryland Route 611 to Assateague Island’s national seashore, which features marshland, pine forest, sandy beaches and paved and unpaved hiking trails. To see how wind and salt have shaped this rugged but beautiful landscape, walk the Life of the Dunes 3/4-mile trail loop. Or pedal along the 8-mile easy out-and-back bike path. You can rent bikes seasonally at the visitor center. 

Where to stay: In Ocean City, the Princess Royale Oceanfront Resort is an all-suites property on the boardwalk’s northern end, a bit quieter area. For wheelchair users, a few of its 338 suites come with wider doors and hand-held showers. It’s pricier than other lodging on this road trip, depending on the time of year, with rates likely to be more than $200 per night.

Terri Marshall, a New York City-based journalist, embarks on road trips at every opportunity. Find more of her road trip stories on the Traveling Mom and A Girls Guide to Cars websites and in Girl Camper magazine.

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