When it opened to pedal pushers and pedestrians alike in 2015, the hope was that the Virginia Capital Trail would be a route dedicated to recreation, healthy living—and, of course, history. The 51.7-mile, multi-use trail runs from Virginia’s past capital of Jamestown to the current capital city of Richmond.

Reflecting on the well-planned pathway’s fifth anniversary last fall, Virginia Capital Trail Foundation executive director Cat Anthony told me that trail usage has exceeded expectations. She boasted, deservingly, about it being the second-most-visited attraction in the Richmond region.

“With over 1.2 million trail counts this past year, it is great to see so many people utilizing this awesome resource for physical and mental health or for transportation,” Anthony said. “We have seen economic growth with businesses and housing pop up along the Capital Trail, and we have also seen people buy bikes and be more active due to having this resource in our community. Trails are a great investment for all communities, and I cannot wait to see what the next five years will hold for the Capital Trail.”

Anthony added that one of the best aspects about the Capital Trail is encountering a wide range of riders, including a mixture of kids learning how to ride a bike, people walking or skating, cyclists who are trying to get in 100 miles of training, and also people commuting to work.

But as rewarding as it is to just ride along this mostly flat, paved, and mile-marked gem, the scenery and stops along the Route 5 corridor make it that much more worthwhile.

“It is fun to bike up the hill leaving Richmond and look back and see the city skyline,” said Anthony when I asked for her insider tips. “I also enjoy going over the Chickahominy Bridge in James City County and viewing the river. Besides the views, I love going to Upper Shirley Vineyards for a glass of wine or heading to Cul’s Courthouse Grille to enjoy a sandwich after my rides.”

With Anthony’s knowledge and notes, and my desire to get active outdoors, I planned three Capital Trail adventures in order to fully experience all of the different sections and what they have to offer—sites, bites, sips and all. Anniversary weekend provided the perfect reason to kick off my inaugural trail trip in Jamestown.

Trail Trip 1: Mile Marker 0 to 19

Billsburg Brewery

Cycle Scene: My husband and I decided to try our new four-bike rack and take our daughters along for our first ride. It seemed many other families had the same idea, as it was a beautiful anniversary weekend day, and the trail was packed with people of all ages. It made sense as we rode over mostly flat, wide paths and on wooden bridges nestled between shady trees. This section proved to be a great option for kids or recreational riders looking for a more leisurely trail trip.

Park: Spaces were plentiful, and free, at Jamestown Settlement. The area has a café, restrooms and plenty of historic attractions to explore before or after your journey.

Stop: We spun our tires for just a few miles before making our first stop at the charming Spoke & Art, a community gathering spot with adorable gifts, outdoor stage, fridge stocked with Virginia beer, and a bike repair station. I couldn’t pass up an iced latte made with Blanchard’s Coffee from Richmond, and we added sandwiches to our order for a picnic lunch at our next detour—Chickahominy Riverfront Park. After a rest here, we headed to Sherwood Forest Plantation—home of President John Tyler—before riding back to our starting point and celebrating with a view of the James City County Marina and a Fly Away IPA at Billsburg Brewery. 

Trail Trip 2: Mile Marker 20 to 39

Melissa-Virginia Capital Trail

Cycle Scene: This time around, we were celebrating another anniversary—ours—so we opted for a solo pedal session with a day date itinerary. This leg definitely took us over more hills but nothing too strenuous. We were motivated by packs of serious cyclists and fresh air as we flew by vast fields and farmland. 

Park: We ditched our car at Charles City Courthouse and decided to fuel up at the throwback Cul’s Courthouse Grille. As we crossed the street to get there, an older gentleman in a red convertible rolled down his window to recommend the burger. I trusted him, and my instincts were right on.

Stop: In my book, dates always involve food and wine, so we used our burger and craft beer calories to keep our legs moving for about 13 miles before veering off the trail toward Upper Shirley Vineyards. Relaxing with a bottle of 2018 Chardonnay on the estate’s epic porch seemed appropriate and well-deserved. We watched an influx of like-minded riders roll up before beginning our trek back. One final stop at Indian Fields Tavern was worth it, as we sat outside drinking a Deschutes Brewery Black Butte Porter and toe-tapping to live music.

Trail Trip 3: Mile Marker 40 to 51.7

Virginia Capital Trail

Cycle Scene: We picked a warm day for our final excursion, and I earned plenty of active minutes and exercise points on what was definitely the toughest Capital Trail segment. My legs felt the elevation changing as we transitioned from the Tidewater to the Piedmont region and approached downtown Richmond.

Park: We unloaded at Four Mile Creek Trailhead and quickly headed west—we had a lot of (not so flat) ground to cover in Henrico County.

Stop: As eager as we were to get to the city’s attractions, we could not pass up a pulled pork sammie at the iconic The Original Ronnie’s BBQ and walking the grounds at the Clarke-Palmore House. When our well-worked muscles made it to Rockett’s Landing, we treated ourselves to local oysters at The Boathouse Restaurant and then a few brews at Hardywood Park. (Once you arrive at the flood wall you’ve officially completed the trail portion of this trip and can ride along Richmond’s Riverfront and Canal Walk and enter downtown.)

Written By

Melissa Stewart

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