Directions from Chesapeake, Virginia to Williamsport, Maryland





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.


Three Days in April 1865

Landmarks – Richmond, Virginia

Inscription. Some of the most dramatic events in Richmonds history occurred during Three Days in April 1865: when the city fell to the Union army after four years of Civil War. , Location. 37° 32.05′ N, 77° 26.659′ ... More on HMDB

McCoy's Ferry

National And State Parks – Clear Spring, Maryland

Inscription. On May 23, 1861 Confederates attempting to capture the ferry boat at McCoy's Landing were driven off by the Clear Spring Guard. Here on October 10, 1862, Gen. J. E. B. Stuart crossed the Potomac on his second ride around ... More on HMDB

Lee and Grant

Landmarks – Doswell, Virginia

Inscription. Lee and Grant faced each other on the North Anna, May 23-26, 1864. Union forces crossed here and four miles to the west but found they could not dislodge Lee's center, which rested on ... More on HMDB

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  • North Anna Other Names: Telegraph Road Bridge, Jericho Mill (May 23); Ox Ford, Quarles Mill, Hanover Junction (May 24) Location: Caroline County and Hanover County Campaign: Grant's Overland Campai... More on Nps.gov

James Fort

Museums – Williamsburg, Virginia

James Fort in Williamsburg, VA is one of more than 15,400 museums in the MuseumsUSA directory. Find an exciting museum to ... More on MuseumsUSA.org

Confederate Soldiers in Elmwood Cemetery / Colonel Henry Kyd Douglas

Landmarks – Shepherdstown, West Virginia

Inscription. Side A, Confederate Soldiers in Elmwood Cemetery: Over 114 Confederate soldiers who were killed at the Battle of Sharpsburg (Antietam) September 17, 1862, or later died of wounds in Shepherdstown, were buried here. They ... More on HMDB

YogaBalance, LLC

Health Club – Henrico, Virginia

We offer Hatha Yoga and Gentle yoga classes for Every Body! See our website for our complete class calendar. More on YogaFinder

Weedons Tavern

Landmarks – Fredericksburg, Virginia

Inscription. Constructed shortly after Fredericksburgs founding in 1728, the tavern across the intersection became a popular gathering place under the proprietorship of its first owner, John Gordon, and then of his son-in-law, George ... More on HMDB

Beacon of Peace

Landmarks – Sharpsburg, Maryland

Inscription. "May it stand as it did in war as a beacon to guide men searching their way through the darkness. May it stand throughout all ages as a symbol of mercy, peace, and understanding.", Mar... More on HMDB

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  • Archives of Maryland (Biographical Series) Clara Barton (1821-1912) MSA SC 3520-13563 Biography: Born Clarissa Harlowe Barton on December 25, 1821 in (North) Oxford, Massachusetts. Daughter of Step... More on Msa.md.gov

The View That Named The City

Landmarks – Richmond, Virginia

Inscription. The curve of the James River and steep slope on this side of are very much like the features of the River Thames in England, at a royal village west of London called Richmond upon Tham... More on HMDB

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  • The Alliance to Conserve Old Richmond Neighborhoods (A.C.O.R.N.) is a nonprofit organization that exists to serve the City of Richmond through the education about and the revitalization of its olde... More on Richmondneighborhoods.org

Sweets for Harpers Ferry

Sightseeing – Harpers Ferry, West Virginia

Inscription. The enticing smell of bread, cakes, candies, and pies undoubtedly attracted many customers to Frederick Roeder's Confectionery, making it a prosperous business from 1845 to 1861. In addition to his store, it is reported ... More on HMDB

Little Falls

Landmarks – Fredericksburg, Virginia

Inscription. On 11 December 1862, Union engineers began the construction of pontoon bridges here so the army could cross the Rappahannock River to Fredericksburg. They began in the morning, hidden by fog. Soon the fog lifted, however, ... More on HMDB

Woodsboro's Tavern

Restaurants – Woodsboro, Maryland

Steak & Ale Restaurant

Restaurants – Hampton, Virginia

The steaks are wonderful by themselves but add a piece of the hawaiin chicken....to die for. Travel through... More on CitySearch

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  • Hearty steaks and seafood platters are served at the family-friendly chain restaurant. User Reviews for Ste... More on CitySearch

  • Inspired by the warmth and charm of an old English Country Inn, Steak and Ale was established in 1966 to pr... More on Virginia.org

Pit Stop LLC

Restaurants – Frederick, Maryland

Stuarts Mortal Wound

Landmarks – Henrico, Virginia

Inscription. Late in the afternoon of 11 May 1864, Maj. Gen. J. E. B. Stuart, the famous Confederate cavalry commander, was mortally wounded just east of here on Old Telegraph Road while rallying t... More on HMDB

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  • Inscription. One half mile to the to the east, on the old Telegraph Road, is a monument marking the field where General J. E. B. Stuart was mortally wounded on May 11, 1864. The monument was erecte... More on HMDB