Directions from Annapolis, Maryland to Winchester, 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.


River Riders

Campgrounds – Bolivar, West Virginia

Middletown

Landmarks – Middletown, Virginia

Inscription. The Virginia General Assembly established Middletown in 1794. Dr. Peter Senseney laid out the original lots for the village. Surrounded by farms and plantations, including historic Belle Grove, the community grew along ... More on HMDB

Lilypons Water Gardens

Gardens – Adamstown, Maryland

Waterlilies by the acre in production ponds and demonstration ponds attract visitors from around the globe. Blooming ... More on Search.visitmaryland.org

Fort Neally

Landmarks – Martinsburg, West Virginia

Inscription. During the French and Indian War, Fort Neally was captured and its garrison massacred, Sept. 17, 1756. Many settlers in the vicinity also were killed. Among captives was Isabella Stockton, later wife of William McCleery, ... More on HMDB

3rd Delaware Infantry

Landmarks – Sharpsburg, Maryland

Inscription. Delaware: 3rd Delaware Volunteers, Major Arthur MaGinnis, 3rd Brigade, 2nd Division, XII Corps, This regiment, worn down from active, service in the second Manassas Campaign, went into... More on HMDB

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  • Born in Philadelphia, Pa. 1842, Charles B. Tanner enlisted in Captain Robert Milligan's Company E, 1st Delaware Infantry Regiment in Wilmington, De. in 1861. He was ... More on Portal.delaware.gov

George Catlett Marshall

Landmarks – Leesburg, Virginia

Inscription. (Left Side Plaque): George Catlett Marshall, (1880-1959): Born Union Town, Pennsylvania, educated at Virginia Military Institute, class of 1901, serving in the United States Army there... More on HMDB

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  • Dodona Manor - Former Home of General George Catlett Marshall "This is Home - a real home after 40 years of wandering." General ... More on Georgecmarshall.org

The Streetcar Era in Catonsville 1880-1963

Landmarks – Catonsville, Maryland

Inscription. For over 100 years, streetcars graced the streets of Baltimore and the heavily traveled #8 line to Catonsville was one of the most popular. This line swung north from Frederick Rd. and plunged into the woods for a brief ... More on HMDB

Fredericktowne Players

Things To Do – Frederick, Maryland

Community theater organization that is open to all interested parties for performance, production, or administrative opportunities. Performs three stage shows each season, Sept to July, plus one s... More on Fredericktourism.org

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  • A nonprofit community theatre company which produces four quality theatrical ... More on Yahoo! Travel

A Way 2 Play Family Sports Center

Things To Do – Edinburg, Virginia

Category: Amusement Park A Way To Play Family Spt Ctr is a one-stop provider of fun for the family in Virginia. Visit ... More on localamusementparks.com

Ice Mountain

Landmarks – Augusta, West Virginia

Inscription. Huge natural refrigerator, five miles north along North River, where ice is found for several hundred yards on the hottest summer days. Raven Rock, on North Mountain, overs one of the finest views in West Virginia. , ... More on HMDB

Fight for the High Ground

Tours – Winchester, Virginia

Inscription. The Shenandoah Valley's strategic location and rich farmland caused it to be the scene of two major Civil War campaigns that comprised hundreds of battles and skirmishes. Many Valley farms, like Rose Hill, became battlefields ... More on HMDB

Building: c1874

Landmarks – Winchester, Virginia

(c1874, VA-34-01) in Winchester , Frederick County, VA. US50 (Amherst St.) W. 0.5 miles from jct with US11/522 to the house on the N. side of the road at 530 ... More on dalejtravis.com

Acropolis Restaurant

Restaurants – Owings Mills, Maryland

Plamondon Company

Restaurants – Frederick, Maryland

Newtown Tavern

Restaurants – Stephens City, Virginia

Casual dining in amazing atmosphere. This restaurant is owned by Cork Street Tavern and also serves the "best ribs in the Valley." Nightlife includes live bands and trivia night, when you can ... More on Virginia.org