Scenic Drives Through Chesapeake Country: A Journey Through Talbot, Caroline & Dorchester Counties
There’s something magical about driving Maryland’s Eastern Shore—where winding roads hug quiet rivers, watermen haul in the morning’s catch, and charming small towns invite you to slow down and explore. Whether you're a seasoned traveler or a weekend wanderer, a scenic drive through Chesapeake Country—specifically Talbot, Caroline, and Dorchester Counties—is the perfect way to discover the heart and soul of the Eastern Shore.
Here’s your guide to a picturesque road trip full of photo ops, roadside treasures, and Chesapeake charm.
Start in Talbot County: Waterfront Views & Timeless Towns
Begin your journey in Easton, the arts and cultural hub of the Shore. Stroll downtown’s historic streets, grab a coffee and visit the free Academy Art Museum before heading out.
Take Route 33 toward St. Michaels, one of Maryland’s most beloved waterfront towns. The drive itself is lined with farmland, marinas, and glimpses of the Miles River. Once in town, explore the Chesapeake Bay Maritime Museum, browse boutiques, or enjoy crab cakes by the water..
From there, continue to Tilghman Island across the drawbridge—one of the best spots for sunset. Watch working watermen head out on the Bay, or pull off the road and enjoy the stillness of this quiet coastal community.
Cruise Through Caroline County: Back Roads & Bucolic Beauty
Loop back through Easton and head north on Route 404, then turn onto Route 328 or Route 16 to enter Caroline County, where you’ll trade shoreline views for pastoral farmland and shady backroads.
Stop in Ridgely or Denton, where Tuckahoe State Park offers miles of forested trails, a peaceful lake, and birdwatching galore. For a taste of local charm, grab lunch at Market Street Public House in Denton or check out The Foundry, a co-op gallery featuring local artists.
Scenic Tip: For a quiet ride, follow River Road out of Denton along the Choptank River—it’s a lesser-traveled stretch with sweeping views and historic homes.
End in Dorchester County: Marshland Majesty & Harriet Tubman’s Legacy
Next, take Route 16 South toward Cambridge, where the landscape shifts again—this time to sweeping tidal marshes, meandering creeks, and big, open skies.
Visit the Harriet Tubman Underground Railroad Visitor Center, bordering the Blackwater National Wildlife Refuge. This area is breathtaking in every season, but fall and winter offer incredible birdwatching—eagles, ducks, and migrating geese fill the skies.
Head into Cambridge, one of the oldest colonial towns in Maryland, for a bite at Blue Ruin or RAR Brewing. Then cruise along Maple Dam Road or Key Wallace Drive—both ideal for sunset drives through golden marshland.
Tips for the Trip:
- Time it right: Early morning or golden hour offers the best light for photos
- Pack binoculars: Especially for Blackwater, Tuckahoe, and any river pull-offs
- Go slow: Many of the most beautiful sights are in the details --farm stands, crabbing docks, osprey nests
Make It a Weekend
Break up the drive by staying overnight in a cozy inn, with a waterfront view, and incredible local dining. Whether you do the full loop in a day or take your time over a weekend, this scenic drive reveals the beauty, diversity, and warmth of Chesapeake Country.
