Authentic Americana is calling – and adventure is the destination. Reconnect with what you love this summer/fall on an epic Virginia road trip. Pack your weekend bag, throw the dog and kids in the car, and hit the road to Hopewell & Prince George! It doesn’t get more Americana than driving the 5 & Dime. The meandering route along Routes 5 & 10 winds its way through Hopewell, Prince George County, Charles City County, Surry County, and James City County, Virginia. Easily done in a day, or spread out over a weekend, the 5 & Dime drive offers history, outdoor adventure, boating, trails, live music, exceptional food and drink, and hidden gems galore. Drive the 5 & Dime and explore Authentic Americana by river and road!

Mileage: 80.6


  • Scenic Virginia Route 5
  • Colonial Plantations
  • Music at The Historic Beacon Theatre
  • Hopewell Riverwalk
  • Biking the Capital Trail
  • Jordan Point Marina
  • Jamestown-Scotland Ferry
  • Jamestown Settlement
  • Indian Fields Tavern
  • The Boathouse at City Point 

The 5 (Route 5)

The North side of the Lower James River is chock full of things to do. Charles City County’s main thoroughfare is historic Route 5, designated a scenic Virginia byway. Historically, Route 5 was a wagon road between Virginia’s Capitol, Richmond, and the former colonial Capitol of Williamsburg. Along Route 5, you will pass a plethora of historic homes and grandiose plantations among them Shirley, Sherwood Forest, Berkeley, and Westover. History lovers revel in the colonial architecture and fascinating stories behind these structures and the people that called them home.

If you want a more active way to experience Route 5, bring your bikes and peddle the Virginia Capital Trail. Ideal access points for Five & Dime travelers are located at Upper Shirley Vineyards, the intersection of Route 5 and 156 (which connects Route 5 & 10 via the Benjamin Harrison Bridge), Charles City Courthouse, and Jamestown Beach by the Jamestown-Scotland Ferry. Didn’t bring your bike? Never fear. There are plenty of rental options in the area, including a guided tour with Basket & Bikes.

For dining options, consider several of the hidden gems located along Route 5. Upper Shirley Vineyards boasts a delicious menu, homegrown wines, and spectacular views of the James River. One of the favorite stops for locals and travelers alike is Cul’s Courthouse Grill. Situated in an old country store, Cul’s offers light fare and is a must-stop for cyclists on the Capitol Trail. They also have frequent live music and trivia nights. Another favorite dining destination is Indian Fields Tavern. This restaurant has an amazing ambiance in an old farmhouse setting. While they are open for lunch and dinner, it’s the ideal spot for Sunday brunch. They often have live music on the weekends, too.

Further along Route 5 in James City County, you’ll find Spoke + Art  Provisions Co. A vibrant destination where delicious food and great coffee meet art and community. Located on a covered porch with a spacious open deck, you can enjoy a menu that’s always changing, offering a variety of sandwiches, salads, pastries, and treats. They have a large assortment of grab-and-go items; perfect to enjoy on your ferry ride across the James River! Additional provisions available include a selection of local beers, wines, ciders, coffee, soft drinks, and snacks.

The Dime (Route 10)

Consider starting the Dime portion of your roadtrip in Downtown Hopewell. For the music lover, check out the schedule of shows at the Historic Beacon Theatre, where you can catch world class performers from Graham Nash to the Oakridge Boys. If you want to get outside, take a stroll along the new Riverwalk at City Park, perfect for sunset views, fishing, and watching the local Ospreys hunt. History enthusiasts will appreciate nearby Appomattox Manor and General Ulysses S. Grant’s Cabin at City Point, headquarters of the Union Army during the Siege of Petersburg and visited by President Lincoln during the Civil War. The beautiful grounds are abundant with photo opportunities (in fact, Appomattox Manor is a favorite backdrop for local wedding photographers). For those that fancy angling, the surrounding waterfront is revered as prime fishing ground. City Point is also one of the best spots around to catch the sunset or sunrise. In fact, it’s what convinced photographer, Pedro Ledesma III, to capture the essence of Hopewell.

Before you head into the countryside, enjoy a meal at the Boathouse at City Point. With a fantastic view of the confluence of the Appomattox and James Rivers, The Boathouse offers a terrific menu, including locally caught oysters, craft brews, and a great wine selection. The Boathouse is perfect for a romantic, sunset dinner on the terrace. Click here for other food options.

Having explored Downtown Hopewell and City Point, turn East and cruise down Route 10 into Prince George County. Once a part of Charles City County, Prince George County became independent when it built a new courthouse on the South side of the River. Named after Prince George of Denmark, the county is home to one of the oldest churches in America, Merchant’s Hope, and one of the largest Czech/Slovak populations in the country, which settled in the little community of New Bohemia.  Near the historic courthouse you will find ziplining at Treetime Adventures, Scotts Park disc golf, and restaurants.

Located less than 2 miles from Route 10, Jordan Point Marina is a delightful gateway gem. At this marina, you have the opportunity to rent both kayaks and pontoon boats. The marina store is well-stocked, offering not only items you might have forgotten at home but also various practical gear. If you’re interested in kayaking, their fleet of single-person kayaks comes with flexible rental options. As for the pontoon boats, you can choose between 8-hour or 4-hour rentals, and they comfortably accommodate up to 8 adults. The best part is that these pontoon boats are also pet-friendly, so you can bring your furry friends along for a great time on the water.

No route is complete without a food stop. Driving East on Route 10, you can pick up Virginia’s best-fried chicken at the Breez-In and begin an affordable art collection by investing 50 cents in a Lamb Arts collectible button. Just after it intersects with Route 31, you’ll find Meats of Virginia which is the perfect place to stock up on cured meats and fresh cuts. Have a sweet tooth instead of a hankering for something carnivorous? Stop in Just for Kicks and grab a world-class ice cream cone or one of their impressive cupcakes.

Before you get to the Ferry, stop in for a meal at Surry Seafood Company. Overlooking Gray’s Creek, near the James River, this picturesque waterfront dining experience offers indoor and outdoor seating. The adjacent marina provides docking space for boats, and there are four comfortable overnight suites available. Since taking over in 2018, Pack Brothers Hospitality has transformed the restaurant into a showcase for Surry County, with plans for future expansions and exciting new ventures on the horizon. Continue down Route 10 and queue up to embark on the Jamestown-Scotland Ferry, which will carry you to the North bank of the James River to the Historic Jamestown Settlement. Here you link back up to Route 5 and the Virginia Capitol Trail where you can loop back to Hopewell.

Sunset on the James River