11 Great Road Trips to Take In The Chesapeake Bay
Some of the best driving around the Chesapeake Bay happens well off the interstate, on highways that wander past fishing towns, broad marshes, old river landings, and quiet peninsula communities. Drivers can cross the Bay itself on the 17.6-mile Chesapeake Bay Bridge-Tunnel, a crossing that passes over open water before dipping beneath it, or devote a day to Eastern Shore harbors such as St. Michaels and Oxford. On the Western Shore, the 47-mile Roots and Tides Scenic Byway links Annapolis with Huntingtown through a string of waterside communities and marinas.
Chesapeake Country Scenic Byway
The Chesapeake Country Scenic Byway is technically 419 miles long, so it is best treated as a mix-and-match Eastern Shore road trip rather than one continuous drive. The Byway's northern gateway is in Chesapeake City, Maryland, near the C&D Canal, then travels south through Chestertown, Kent Island, Cambridge, and Crisfield. The route stretches along a wide section of shoreline, so it splits well into two or three days or a single section at a time.
The northern part of the Scenic Byway is more river-oriented, with historic port towns, marinas, and roads that pass farm fields before reaching the water. Kent Island, around Kent Narrows and Stevensville, is a good rest stop after crossing the Bay Bridge. Farther south, St. Michaels and Oxford have boatyards and maritime history, and Cambridge is a handy base for trips into Blackwater National Wildlife Refuge. The final stretch toward Crisfield becomes flatter and more remote, with marshland, seafood docks, and the Tangier Sound taking over the view.
Annapolis to Huntingtown
The drive from Annapolis to Huntingtown follows the Roots and Tides Scenic Byway, passing through the quieter side of Anne Arundel and Calvert counties. It is only about 47 miles, but it works as a slow coastal drive because it passes through waterside communities that are easy to skip on a longer trip. This route travels past the US Naval Academy and the Maryland State House. Georgian-era inns along the way include the Patterson House and Georgian House Bed & Breakfast.
The trip gradually leaves behind Annapolis traffic of MD 2 and moves toward roads lined with marinas, creeks, small seafood businesses, and houses built close to the Bay. Deale and Shady Side are waterfront villages that are close to the working docks. North Beach and Chesapeake Beach have public waterfront access, a boardwalk setting, and a handful of casual places to stop without planning every detail. Breezy Point Beach is a good detour for beach access before continuing inland.
Lower Susquehanna Byway
The Lower Susquehanna Byway is a different kind of Chesapeake Bay road trip because it follows the Susquehanna River shortly before it reaches the Bay. The route stretches from Havre de Grace to Perryville, using MD 155 and MD 161. The route joins US 1 to cross over the river directly on top of the Conowingo Dam. It is about 33 miles with river overlooks, Piedmont forests, and older industrial areas that make it more varied than many flatter Bay drives.
Havre de Grace is home to Concord Point Lighthouse, Millard Tydings Memorial Park, Keeper's House Museum, and views across the river mouth. From there, the road heads inland through rolling terrain toward the Conowingo Dam area. Pull-offs and viewing areas near the dam draw crowds during bald eagle activity periods, although access and parking can vary. The final section toward Perryville travels south along the east bank of the river, passing through the historic waterfront town of Port Deposit and ending near attractions like Rodgers Tavern and the Great Wolf Lodge.
Harriet Tubman Underground Railroad Byway
The Harriet Tubman Underground Railroad Byway winds through the Dorchester and Caroline County landscape where Harriet Tubman was born, lived, and began her journey to freedom. From Cambridge, the route passes through towns central to African-American history, including Church Creek, Woolford, East New Market, Preston, Denton, and Goldsboro. The route through Maryland is about 125 miles, with another 98 miles in Delaware.
This drive passes through farmland, pine woods, and wetlands connected to the Blackwater River. It starts at the Harriet Tubman Underground Railroad Visitor Center near Church Creek, then continues through the Blackwater area before heading north and east toward Preston and Denton. Key stops include the Harriet Tubman Museum & Educational Center, the Dorchester County Courthouse, Brodess Farm (where Harriet grew up), and Bucktown General Store.
Cambridge to Crisfield
The drive from Cambridge to Crisfield follows the lower Eastern Shore toward the Tangier Sound waterfront. The direct distance is about 65 miles, but a complete drive includes a few detours through places like Princess Anne and Janes Island State Park. It is a full-day route with long open stretches, low marshland, and a noticeable shift from larger towns to smaller fishing communities.
From Cambridge, the route follows MD 16 West, with time for the 4-mile Wildlife Drive in Blackwater National Wildlife Refuge before a detour toward Hoopers Island. The peninsula road to Hoopers Island leads past seafood docks and water on both sides in some areas. Back on the main route, Salisbury is an easy place to stop before the road continues south through Somerset County. Near Crisfield, Janes Island State Park has marsh views, boat access, and short walking opportunities. The drive ends near Crisfield's docks, where ferries depart for Smith Island.
St. Michaels to Oxford
The route from St. Michaels to Oxford combines waterfront towns, narrow peninsula roads, and a ferry ride across the Tred Avon River. It is a short drive, generally under 40 miles, but it grows into a fuller day with Tilghman Island and the Oxford-Bellevue Ferry added. This route is a common choice for bikers, and the Harbour Inn even lends complimentary bicycles to guests.
St. Michaels is near the Chesapeake Bay Maritime Museum, harbor, and Talbot Street shops. From there, MD 33 leads toward Tilghman Island, where marinas, fishing boats, and the Knapps Narrows drawbridge create a more working-waterfront setting. After a loop around the island, the route heads back toward Bellevue for the ferry crossing. The Oxford-Bellevue Ferry turns a simple road trip into a loop and saves drivers from retracing every mile. However, drivers should check the ferry schedule in advance because hours can change by season and weather conditions. In Oxford, the docks, the waterfront Oxford Town Park, and the boatyards make an easy walk before the drive continues to another town like Easton or returns to St. Michaels.
Kent Island to Rock Hall
Kent Island to Rock Hall is a good upper Eastern Shore road trip for drivers who want to move from the Bay Bridge area into quieter river towns and harbor communities. The trip mainly follows MD 8, US 50, and MD 213 and totals about 50 miles, although stops along the Chester River or a detour to Betterton Beach easily turn it into a full-day drive.
Kent Narrows has waterfront restaurants like The Jetty and wide views of the channel between Kent Island and the mainland. From there, the route heads through Queen Anne's County farmland toward Centreville and Chestertown. Chestertown is the best stop along the way, with Zelda's Speakeasy, Evergrain Bread Company, and Washington College nearby. The drive ends in Rock Hall, where Eastern Neck National Wildlife Refuge and Waterman's Museum give the drive a maritime ending.
Colonial Parkway and York River
The Colonial Parkway connects Jamestown, Williamsburg, and Yorktown across about 23 miles of protected parkland. It is not a fast route, and that is why it works as a road trip. The road has low speed limits, brick bridges, wooded curves, and occasional water views that make it appear separated from the busier highways surrounding the Historic Triangle, like I-64 or Route 199.
The drive begins on the James River side of the parkway, with stops at Jamestown Settlement or Historic Jamestowne. The parkway continues toward Williamsburg, where Colonial Williamsburg, the Capitol, and Duke of Gloucester Street make a natural longer break. The eastern segment becomes more wooded and passes near College Creek and the York River. Pull-offs along the way give chances to step out and look over the water rather than drive straight through. The parkway ends in Yorktown at Yorktown Battlefield, where the last major battle of the Revolutionary War took place.
Fredericksburg to Reedville
The Northern Neck drive in Virginia, from Fredericksburg to Reedville, follows Route 3 and US 360. Route 205 makes a scenic detour to Colonial Beach before rejoining Route 3. The route travels about 100 miles across the peninsula between the Potomac and Rappahannock Rivers. The landscape changes gradually from inland roads to flat tidewater country. Good stops include Caledon State Park, where trails lead toward the Potomac River, and the George Washington Birthplace National Monument.
The route continues through Warsaw, Virginia, where the Richmond County Museum and guided tours of Menokin, a Georgian-style mansion, break up the drive, before the main road heads toward Kilmarnock and Irvington. Fish Hawk and The Tides Inn in Irvington are good lunch stops. The route heads southeast toward Reedville, a historic fishing village on Cockrell Creek. Its waterfront reflects the region's menhaden industry, with large commercial vessels and former company buildings near the harbor. An extended route can add Westmoreland State Park, Stratford Hall, or Tangier Island before returning inland.
Middle Peninsula River Roads
This Middle Peninsula road trip is a loose loop rather than a fixed point-to-point drive. The route totals about 90 miles before detours, and the trip has plenty of diversions along the way. Machicomoco State Park, for one, celebrates Indigenous people of Virginia. Gloucester Courthouse is close to the York River and a number of routes into the peninsula. From there, Route 14 heads east through Mathews County, where farmland, creeks, and small crossroads replace larger commercial corridors.
Routes 3 and 33 lead to Deltaville, a major boating center with more boats than people and marinas clustered around Jackson Creek and Broad Creek. The loop continues north toward Urbanna, home of Virginia's annual Oyster Festival near the Rappahannock River waterfront and historic district. The drive can finish on US 17 at Tappahannock beside the river or loop back through smaller communities to Gloucester. This road trip is best for unplanned detours toward the water rather than following a tightly scheduled itinerary.
Virginia Beach to Chincoteague
The nearly 100-mile drive from Virginia Beach to Chincoteague begins with one of the Chesapeake Bay's most distinctive crossings. The Chesapeake Bay Bridge-Tunnel stretches 17.6 miles over and beneath the Bay, taking about 25 minutes to cross in normal conditions. Once on the Eastern Shore, the route follows US 13 through Cape Charles, Onancock, and other small communities before turning east on Route 175 toward Chincoteague.
In Cape Charles, Mason Avenue leads toward the public beach. From there, US 13 continues north through the Eastern Shore's agricultural center. Onancock is a good detour for stops like Ker Place or the historic Charlotte Hotel and Restaurant, and the small towns along the highway give easy opportunities for fuel and food. Route 175 leads east on the final approach to Chincoteague, where marshes and water views become more prominent. Beyond town, Assateague Island National Seashore has beach access, wildlife viewing, and a chance to see the area's famous wild ponies. The Maryland entrance to Assateague is separate, and travel between the two districts requires a return to the mainland.
Plan the Drive, Not Just the Stops
The best Chesapeake Bay drives leave room for an unscheduled stop and treat the drive as part of the destination. The best outings center on one or more main stops, such as St. Michaels or Chincoteague, with time left for smaller detours to public landings, seafood docks, riverfront parks, and wildlife areas. A slower route often reveals more of the region than trying to take in a few peninsulas in one day.
Conditions for bridges, ferries, and wildlife refuges deserve a check before leaving. Maryland's Bay Bridge can be heavily congested on weekends, and the Chesapeake Bay Bridge-Tunnel may have weather-related delays. Ferry schedules and access to beach or refuge roads can change because of seasonal demand, maintenance, or severe weather.
