Directions from Virginia Beach, Virginia to Gloucester, 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.


Ditch and Mound

Landmarks – Williamsburg, Virginia

Inscription. Dozens of open ditches crisscrossed Jamestown. A ditch and its mound could mark a property boundary, line the edge of a road, or drain swampy soil. Ditches also served as handy trash dumps. Two major ditches, several ... More on HMDB

Bay Creek Golf Club

Golf Courses – Cape Charles, Virginia

They were actually draining a pond the day I played which hindered the atmosphere some, but overall this is... More on Yahoo! Travel

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  • EVERYONE loved Aqua Restaurant and the food was FANTASTIC. More on TripAdvisor

  • I played this course a couple years ago and found the layout to be very solid, but the conditions were stil... More on Yahoo! Travel

Alexandria Park

Parks – Portsmouth, Virginia

Ohio & Scioto River within walking distance More on KaBoom.org

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Yorktown Battlefield

Things To Do – Williamsburg, Virginia

This museum is best sui More on igougo

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  • To complete the historic anniversary weekend, I took the Colonial Parkway to Yorktown. This is the site of the famous surrender of ... More on igougo

  • There are so many battlefields in this area, so we decided to visit at least this famous one. You go to the visitors center first ... More on igougo

Championship Golf Course

Golf Courses – Williamsburg, Virginia

On several holes, you really need to weigh risk / reward before you pull out the driver. More on golflink.com

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  • Greens like pool table tops, yet very fair. More on golflink.com

  • Wow, what a beautiful course! Very challenging. Must hit fairways to score well. Excellent! More on golflink.com

Presidents Park

Things To Do – Williamsburg, Virginia

We visited last summer when it was a small gift shop, some overpriced snacks at a cafe and the park itself. More on KidsPlayParks

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  • This walk-through park contains a 17-foot concrete bust of all the US presidents. There are signs at each stop containing very informative ... More on igougo

  • Oh lord, where to begin? President's Park, in the words of the website, ".features 16-18 foot busts of all 43 Presidents of the United States, p laced in a garden setting." In other words, it\'s a ... More on KidsPlayParks

Monticello Arcade

Landmarks – Norfolk, Virginia

Designed by Neff & Thompson in the Beaux Arts Classical style, the Monticello Arcade was built in 1908 and is one of only two shopping arcades in Virginia. It features elaborate terra cotta decora... More on Visitnorfolktoday.com

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  • Designed by Neff & Thompson in the Beaux Arts Classical style, the Monticello Arcade was built in 1908 and is one of only two shopping arcades in Virginia. It features elaborate terra cotta decorat... More on Visitnorfolktoday.com

New Point Comfort Lighthouse

Landmarks – New Point, Virginia

Here is the view of the lighthouse from the wooden walkway at the preserve using a telephoto lens. If you want to get closer, ... More on LighthouseFriends.com

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  • Standing at the end of what was once the southernmost peninsula in Mathews County, now surrounded by water and hundreds of yards from the mainland, the lighthouse marks the entrance to Mobjack Bay.... More on Virginia.org

  • The Chesapeake Bay boasted the greatest shipping volume in North America during the 1700s and early 1800s, prompting America's new federal government to establish lighthouses for guiding vessels to... More on LighthouseFriends.com

Steubens Division

Things To Do – Yorktown, Virginia

Inscription. The 2,000 men of Major General Baron Von Steubens American Division bivouacked in the woods and fields to the right of the road. They were chiefly Pennsylvania, Virginia and Maryland units, and some others, such as sixty ... More on HMDB

The Venue at 35th Street

Landmarks – Norfolk, Virginia

A cousin of the Generic Theater, The Venue at 35th Street is striving to be an open-minded venue for poetry readings, staged script readings and slam poetry. They have also constructed the city's first outdoor stage, which will eventually ... More on NorfolkCVB.com

Moonstar III Incorporated

Restaurants – Yorktown, Virginia

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Rose & Crown Restaurant

Restaurants – New Kent, Virginia

The atmosphere is lovely and the service is friendly. More on TripAdvisor

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  • Prices at lunch are very reasonable. More on TripAdvisor

  • Had lunch there in an old remodeled historic building. Had a chicken salad sandwich that seemed to have blu... More on TripAdvisor

Sandpiper Reef

Restaurants – Hallieford, Virginia

Opened for the season with our new chef, Jamie Atwood, cooking up a menu to include several old favorites and many wonderful new dishes. Thursdy-Saturday, 5-9 pm ... More on Virginia.org

Battleship Wisconsin: Berthed in Norfolk the Homeport of Naval History

Landmarks – Norfolk, Virginia

Inscription. Redefining the skyline of downtown Norfolk, battleship Wisconsin stands stoically with dominating presence. After months of dredging and construction, Wisconsin majestically slipped in... More on HMDB

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  • Inscription. Battleships bearing the name Wisconsin have graced the waters off Norfolk and Hampton Roads since the beginning of the twentieth century. Ornately designed to show-off the “Stars... More on HMDB

Cheyenne Supper Club

Nightlife – Hampton, Virginia

Casual yet upscale dining to live entertainment and rockin' country boot scootin' fun. Great lunch specials. More on Virginia.org

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  • Enjoy good times, pleasant dining & great cuisine at the Cheyenne Supper Club! - The casual atmosphere is great for family & friends - Menu features an extensive array of selections & full-service ... More on entertainment.com