Directions from Chesapeake, Virginia to Oakland, 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.


Indian Treaty of 1646

Sightseeing – West Point, Virginia

Inscription. Shortly after paramount chief Opechancanoughs 1644 attacks on English settlers in response to the settlers encroachment on Indian lands, he was captured and put to death at Jamestown. His successor Necotowance signed ... More on HMDB

Civil War Earthworks Preservation Message

Things To Do – Spotsylvania, Virginia

Inscription. The gentle mounds that meander through Spotsylvania Court House battlefield once looked like the reconstructed earthwork in front of you. The armies built more than 12 miles of trenches here, using whatever tools they ... More on HMDB

Bolling Haxall House

Landmarks – Richmond, Virginia

Home to the Woman's Club since 1900, the Italianate-style Bolling Haxall House was built in 1858 for Bolling Walker Haxall, heir to a ... More on Visitrichmondva.com

More Reviews
Close
  • The Bolling Haxall House, an imposing Italianate mansion in the heart of downtown Richmond, was built in 1858 for prosperous business leader Bolling Walker Haxall. The house was purchased in 1900 b... More on Virginia.org

Southern Firepower

Landmarks – Richmond, Virginia

Inscription. This 6.4-inch Brooke rifled canon represents one of the greatest sources of pride for the Confederacy. Named for its inventor, John Mercer Brooke, this type of gun was renowned for its... More on HMDB

More Reviews
Close
  • Robert Edward Lee was born on January 19, 1807 at "Stratford" in Westmoreland County, Virginia, to Henry and Anne Hill Lee. Henry Lee was a distinguished cavalry officer who participated in the Ame... More on Nps.gov

Samuel Pleasants Parsons House

Landmarks – Richmond, Virginia

Inscription. Completed in 1819, 601 Spring Street was the home of Samuel Pleasants Parsons (1783-1842). Parsons, a Quaker, was an early reform-minded superintendent (1816-1822, 1824-1832) of the Vi... More on HMDB

More Reviews
Close
  • The Samuel Pleasants Parsons House, located in the historic neighborhood of Oregon Hill in Richmond, was built in 1818 for Samuel Parsons, a prominent Quaker and superintendent of the nearby state ... More on Dhr.virginia.gov

Smoothie King

Smoothies – Richmond, Virginia

Be good to yourself - Over 50 different flavors of custom-made, all natural ingredients including real fruit & juices - Nutritional smoothies, ... More on entertainment.com

Cornwallis' Cave

Landmarks – Yorktown, Virginia

And then to find out that it is probably not really the cave that Cornwallis stayed in...but it is free a... More on Yahoo! Travel

3.5
1 review
1 source
Average Rating
3.5 out of 5
1 review
1 source
Yahoo! Travel
3.5
1+ reviews
Close
More Reviews
Close
  • I remember visiting the area as a child and it was wide open to enter. Now there are bars covering the entr... More on Yahoo! Travel

  • Walking the narrow streets of Yorktown allows one to become immersed in the 300 years of history the town ... More on Virginia.org

Oakland - Garrett County Historical Museum

History Museum – Oakland, Maryland

The Garrett County Historical Society Museum houses local history exhibits such as early mining tools, Native ... More on PlanetWare

George Washington Masonic Museum / Masonic Lodge No 4

Museums – Fredericksburg, Virginia

Young George Washington was raised a Mason in this lodge in 1752. The lodge museum today contains memorabilia and relics relating to his ... More on Virginia.org

Linden Vineyards

Wineries And Vineyards – Linden, Virginia

I will not be going back nor will I recommend this vineyard or its wine to anyone ever again. More on TripAdvisor

3.0
10 reviews
1 source
Average Rating
3.0 out of 5
10 reviews
1 source
TripAdvisor Loading
Close
More Reviews
Close
  • They have two tastings, a free one upstairs, and a premium wine tasting for More on igougo

  • Located a bit more than an hour from Washington, DC out Rte 66, Linden is a larger winery with a great vari... More on igougo

Mattaponi Winery

Wineries And Vineyards – Spotsylvania, Virginia

Take a taste in time with Mattaponi Wine. The name comes from the three rivers in Spotsylvania County: Matta, Po, and Ni, which has been used in history to name the Indian tribe once ruled by Chie... More on Visitfred.com

More Reviews
Close
  • Take a taste in time, with Mattaponi Wine! The name comes from the three rivers in Spotsylvania County: Matta, Po, and Ni. Mattaponi has been used in history to name the Indian tribe once ruled by ... More on AppellationAmerica.com

Birth of Naval Aviation

Landmarks – Newport News, Virginia

Inscription. “ The value of the aeroplane for the Navy is unquestioned. ” – Eugene B. Ely, Naval aviation dates from November 14, 1910, when stunt pilot Eugene B. Ely coaxed a Curtiss “Pusher” biplane ... More on HMDB

Zipeez

Restaurants – Oakland, Maryland

Harbor Espresso Cafe

Restaurants – Poquoson, Virginia

Best coffee in town! - Our menu features an extensive line of hot & cold specialty beverages, a limited sandwich menu, breakfast sandwiches & homemade pastries anytime - ... More on entertainment.com

3.5
1 source
Average Rating
3.5 out of 5
overall rating
CitySearch
3.5
overall rating
Close

Padow's Hams and Deli - City Hall, Richmond

Restaurants – Richmond, Virginia

an over priced deli. Good food but you'll pay for it. More on TripAdvisor

3.5
3 reviews
2 sources
Average Rating
3.5 out of 5
3 reviews
2 sources
TripAdvisor Loading
CitySearch
4.5
overall rating
Close
More Reviews
Close
  • I have never even went to Padows Hams and Delis INC. but I have heard of it and seen the place !! More on TripAdvisor

  • Located inside City Hall, 900 East Broad Street. Enter from lobby or Broad St near 9th, across from the Lib... More on Virginia.org