Directions from Winchester, Virginia to Cape Charles, Virginia





UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.


New Point Comfort Lighthouse

Landmarks – Port Haywood, Virginia

Inscription. Standing at the end of what was once the southernmost peninsula in Mathews County, now surrounded by water, the lighthouse marks the entrance to Mobjack Bay. Authorized by Congress in 1801, this 55-foot-high sandstone ... More on HMDB

Gym for Woman

Health Club – Virginia Beach, Virginia

Emphasis is placed on the balance between body, mind, and spirit, with class time divided between practicing beginner Hatha Yoga postures and learning how to completely relax ~ both physically *AND* ... More on YogaFinder

Hunters Iron Works

Landmarks – Fredericksburg, Virginia

Inscription. Located south of here on the Rappahannock River, stood Hunters Iron Works, founded by James Hunter and was in operation by the 1750s. With the outbreak of the American Revolution, the Rappahannock Forge there supplied ... More on HMDB

Pratt John Lee Memorial

Themeparks – Fredericksburg, Virginia

Category: Amusement Park Pratt John Lee Memorial is a quality source of laughter and enjoyment in Virginia. Visit us ... More on localamusementparks.com

Start of Sheridan's Raid

Landmarks – Fredericksburg, Virginia

Inscription. Here Sheridan, moving from camp, came into the Telegraph Road on his raid to Richmond, May 9, 1864, while Lee and Grant were fighting at Spotsylvania. The 10,000 Union Cavalry filled the road for several miles. Turning ... More on HMDB

Omaha Beach Memorial Tree

Beaches – Fort Monroe, Virginia

Inscription. This tree, planted with authentic soil from Omaha Beach of Normandy, France, commemorates the 40th anniversary of Allied forces landings on 6 June 1944. It stands as a memorial to sacrifices in battle and a tangible symbol ... More on HMDB

Totopotomoy Line Confederate Works

Landmarks – Mechanicsville, Virginia

Inscription. Crossing the road at this point were Federal entrenchments heavily shelled by the Confederates in the operation of May 29-30, 1864, immediately preceding the Second Battle of Cold Harb... More on HMDB

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  • Inscription. Fortifications on this hill mark the strong confederate works along Totopotomoy Creek, prepared as a defensive position in General Lees withdrawal from the Rapidan to the James. Engage... More on HMDB

Edmund Pendleton's Home

Landmarks – Milford, Virginia

Inscription. Six miles southeast is the site of Edmundsbury, home of Edmund Pendleton. Pendleton, born September 9, 1721, was in the House of Burgesses; a delegate to the Continental Congress; chairman of the Virginia Committee of ... More on HMDB

The Courthouse

Landmarks – Fredericksburg, Virginia

Built in 1853, this courthouse is a fine example of Gothic Revival architecture. In fact, its architect, James Renwick, also designed St. Patrick's Cathedral in New York and the original Smithsoni... More on Frommers

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  • Inscription. With the arrival of the Union army in the Spring of 1862, Fredericksburg-area slaves by the hundreds fled to freedom. To house the refugees, the Union army transformed the basement of ... More on HMDB

Kingston Parish

Museums – Mathews, Virginia

Inscription. Kingston Parish was established about 1652. During colonial times, the Anglican parish administered the ecclesiastical and some civil affairs for the inhabitants of the area that later... More on HMDB

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  • Kingston Parish in Mathews, VA is one of more than 15,400 museums in the MuseumsUSA directory. Find an exciting museum to ... More on MuseumsUSA.org

Gen. Hooker's Headquarters

Landmarks – Fredericksburg, Virginia

Inscription. Just northeast, Maj. Gen. Joseph Hooker, commander of the Union Army of the Potomac, kept his headquarters, Jan. June 1863, amid a vast city of tents and camps. It was here he rehabili... More on HMDB

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  • Gen. Hooker's Headquarters N-34 Gen. Hooker's Headquarters N-34 Just northeast, Maj. Gen. Joseph Hooker, commander of the Union Army of the Potomac, kept his headquarters, Jan.-June 1863, amid a va... More on Dhr.virginia.gov

Richard's Rendezvous

Restaurants – Richmond, Virginia

Adorned in Sparkling Jewelry, Exotic Lingerie, and little else you will be drawn to her beat. More on CitySearch

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4 reviews
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4.0 out of 5
4 reviews
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4.5
2+ reviews
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  • Being in town on business, I only got to visit Richard's late at night, but it kept me going through the ne... More on CitySearch

  • The scenery!!! More on TripAdvisor

Cracker Barrel Old Country STR

Restaurants – Richmond, Virginia

I asked for napkins to try to clean off the damage, but she initlally ignored me. More on TripAdvisor

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3 reviews
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  • They seated 8 of us right away. The place was busy but there was no line waiting. Food was very good. Waitr... More on TripAdvisor

  • We entered Cracker Barrel with our very large party of family on Sunday morning - one of their busiest time... More on TripAdvisor

Kettle

Restaurants – Hampton, Virginia