Block Island to Winston-Salem: A Coastal to Piedmont Road Trip

Block Island, RI sits 12 miles off the Rhode Island coast, accessible via the Block Island Ferry from Point Judith. The ferry ride to the mainland takes about 55 minutes on the high-speed ferry, or 2 hours on the traditional car ferry. Once you drive off the ferry at Galilee, you face a 688-mile journey to Winston-Salem, NC, weaving through Connecticut, New York, New Jersey, Pennsylvania, Maryland, West Virginia, Virginia, and finally North Carolina.

This road trip crosses three distinct physiographic provinces: the Atlantic Coastal Plain, the Piedmont Plateau, and the Appalachian Mountains. You will traverse the Delaware Water Gap, the Shenandoah Valley, and the Blue Ridge Parkway corridor. The drive takes approximately 11 hours of pure driving time, but with recommended stops, plan for two full days.

One historical fact: the route roughly follows the old Philadelphia Wagon Road, used by 18th-century settlers moving south. The road passes through the historic towns of Princeton, NJ; Philadelphia, PA; and the site of the Battle of Guilford Courthouse near Greensboro, just east of Winston-Salem.

Total: 688 miles, about 11 hours of driving, not including ferry time. Best budget 2 to 3 days for a relaxed trip with sightseeing.

Road quality is generally good along interstates. I-81 in Virginia can be heavily trafficked with trucks; maintain a safe following distance. In West Virginia, the roads may have sharp curves and elevation changes. Winter weather can impact the drive, especially in the Appalachian sections. Check forecasts and carry an emergency kit.

Family-Friendly Stops:

• Please Touch Museum (Philadelphia, PA) – interactive children’s museum
• Smithsonian National Zoo (Washington, DC) – free admission
• Luray Caverns (Luray, VA) – underground wonder with stalactites
• Natural Bridge State Park (VA) – 215-foot limestone arch

Fatigue Management: Plan to stop every 2 hours or 100 miles. Safe rest areas: James River Rest Area (mile 169 on I-81), Virginia Welcome Center (I-81 near the NC border). For overnight, Harrisonburg or Roanoke are ideal.

Pet-Friendly Framework: Most rest stops have pet relief areas. Many hotels along the route allow pets; chains like La Quinta and Motel 6 are reliably pet-friendly. In Winston-Salem, the Tanglewood Park offers dog-friendly hiking trails.

The route offers diverse natural landscapes: from the Atlantic coast of Rhode Island and Connecticut, to the rolling hills of the Piedmont in North Carolina. Along the way, you cross the Delaware River at the Delaware Water Gap (a National Recreation Area), the Blue Ridge Mountains, and the Shenandoah Valley.

Natural Attractions:

• Delaware Water Gap National Recreation Area (PA/NJ) – hiking, waterfalls, and scenic overlooks
• Shenandoah National Park (VA) – Skyline Drive parallels I-81; great for leaf-peeping
• Blue Ridge Parkway (VA/NC) – 469 miles of scenic road, especially the segment near Roanoke
• Hanging Rock State Park (NC) – just off I-40 near Winston-Salem, with waterfalls and granite domes

Local Commerce and Culture: The route passes through historic towns known for their local crafts and food. In Staunton, VA, visit the Woodrow Wilson Presidential Library. In Lexington, VA, explore the Virginia Horse Center. In Mount Airy, NC (Andy Griffith’s hometown), see the original Mayberry. Winston-Salem itself is known for its Moravian heritage, the Reynolda House Museum of American Art, and the Old Salem historic district.

The primary route is I-95 South from New Haven to Washington, DC, then I-66 West and I-81 South through Virginia, finishing on I-40 West and Business 40 into Winston-Salem. An alternative scenic route is the Blue Ridge Parkway from Waynesboro, VA to Asheville, NC, then I-40 East, adding 2 hours but offering panoramic views.

Fuel costs: as of 2025, gasoline averages $3.30/gallon nationally. For a 25-mpg vehicle, expect to use about 27.5 gallons, costing roughly $91. Tolls: the New Jersey Turnpike (I-95) and Delaware Memorial Bridge have tolls totaling around $15. The Chesapeake Bay Bridge-Tunnel is an optional scenic detour adding $14.

• Key highways: I-95 South, I-66 West, I-81 South, I-40 West
• Alternative: Blue Ridge Parkway (VA to NC) – slower but scenic
• Rest areas: Every 30-40 miles along interstates; notable ones: James River Rest Area (I-81), Virginia Welcome Center at the state line

Accommodation: mid-range hotels average $120-160/night. Consider booking in Harrisonburg, VA or Roanoke, VA for a halfway stop. For a budget option try hotels near Staunton, VA.

For a detailed guide on planning stops, see how to find the best stops and hidden gems between cities.