Richmond to Colonial Williamsburg Weekend Cycling

Trip Length 4 Days
Group Size 4?11
Activity level
Starting from
$1,299 for REI Members
$1,429 for non-members
Departures Sep 2020-Oct 2020

Four days of laid-back cycling on quiet country roads and the Virginia Capital Trail, on this cycling tour of American history. Ride from Richmond to Colonial Williamsburg, with stops in the historic settlements of Jamestown and Yorktown along the way.

Discover Virginia?s important place in American history on this four-day cycling tour of some of our nation?s most important cultural and historical sites. Our tour starts in Richmond, the capital of the Confederacy for most of the Civil War. Visit Jamestown, the first successful English settlement of what is now the United States, founded in 1607. We?ll roll through Yorktown, the site of the final battle of the American Revolution, and visit the living museum that is Colonial Williamsburg. We explore the rich heritage of our early nation as we take an easygoing cycling tour through Virginia?s historic triangle on trails, parkways and roads that are generally flat to lightly rolling. This four-day excursion brings together the scenic landscapes of the Virginia lowlands with its abundant wildlife, inspiring history, and charming historic towns filled with quaint shops and local artisans.

We have e-bikes available for anyone who finds the mileage beyond their reach, so that partners, friends or solo riders can stay in proximity of the full group, while still enjoying the beauty of the Commonwealth of Virginia.

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Trip Highlights

  • Ride the car-free Virginia Capital Trail from Richmond to Jamestown
  • Visit the historic Yorktown Battlefield, Colonial Williamsburg and Chippokes Plantation
  • Explore Jamestown, the first successful English settlement in North America
  • Cycle the smooth, scenic Colonial Parkway from Jamestown to Yorktown
  • Experience three nights of REI Classic Camping


This trip is rated Easy Active[2]. The route includes the Virginia Capital Trail, the lightly traffic Colonial Parkway, and rural Virginia roadways. Participants should comfortable in the saddle for 3?4 hours per day. Rides consist of days covering 10?45 miles in distance with total daily elevation gains less than 1200'. Vehicle support will be available throughout the trip when needed to shorten any day. E-Bikes are available in limited quantity as well.

We recommend a conditioning program beginning at least 1?2 months prior to departure that incorporates rides of at least 15?25 miles. The better cycling shape you're in, the more you'll enjoy all this trip has to offer!

  • Cycling
  • Road Cycling

What's Included

Lodging and meals as indicated on the daily itinerary; professional guide services; flat or drop bar road bike or e-bike (guest's choice); transportation during the course of the trip; park entrance fees.


REI Classic Camping, 3 nights

Your wheels for the journey

Every great tour begins with a great bike, and our top-flight fleet has been carefully curated for your cycling adventure.

Want to bring your own bike?  You can do that too.

Your Adventure Itinerary

Day 1

Cycling the Virginia Capital Trail

Meeting in the lobby of our host hotel at 8am, we start with an orientation and a quick bike fitting. Today?s ride is the longest by mileage but might be the easiest day of the trip. We begin at the host hotel and travel along the Virginia Capital Trail towards Jamestown. The 51-mile paved bike path connects the modern and original capitals of Virginia?Richmond and Jamestown. Along the way we stop to visit the Civil War Visitor Center at Tredegar Iron Works, which documents the history of Richmond as the iron and coal center of the south during the Civil War. We continue along to our trail-side lunch stop prepared by the guides before continuing on to our campsite near the banks of the Chickahominy River. As the guides prepare our evening meal, we can kick back and relax or take a walk to explore the park. Lunch and dinner included.

Cycling: 46 miles (5?6 hours, paved trail), Elevation gain/loss: +1,025'/-1,081'

Day 2

Visit Jamestown and Chippokes Plantation State Park

After a hearty breakfast and we break camp. Today we take a leisurely ride along the remainder of the Virginia Capital Trail to Jamestown. Jamestown was the first successful English settlement in North America, founded in 1607. We take time to explore its archeological sites and ride the loop road around Jamestown Island. After a guide-prepared lunch we take the Jamestown-Scotland ferry across the James River and cycle along rural, lightly rolling roads to our home for the evening: Chippokes Plantation State Park. Chippokes Plantation is one of the oldest operating plantations in the commonwealth and has been in continuous operation for 400 years. Here we can explore the visitor center, farm museum, the beach overlooking Jamestown Island, or the historic exhibits and buildings traversed by the many hiking trails. We pitch camp here for the evening and enjoy a guide-prepared dinner and some relaxing time around the campfire. All meals included.

Cycling: 25 miles (3?4 hours, paved road), Elevation gain/loss: +550'/-505'; Ferry: 30 mins

Day 3

Explore Colonial Williamsburg and its historic surroundings

As the sun rises on the horizon, burning off any lingering morning fog, we break camp after breakfast and loop back toward the Jamestown-Scotland ferry. After the ferry crossing we bike the Colonial Parkway until we reach Williamsburg?s historic center, and the Revolutionary War-era, living museum that is Colonial Williamsburg. Dressed in period clothing, performing period tasks, the staff of Colonial Williamsburg delight us with historic stories of life long ago. We have lunch at a well-known local restaurant, then mount our trusty steeds and head to our accommodations for the evening just outside Yorktown, VA. All meals included.

Cycling: 36 miles (3?5 hours, paved road), Elevation gain/loss: +1,176'/-1,207'

Day 4

Discover historic Yorktown and return to Richmond

On our final day together we cycle around Newport News Park, making our way to Yorktown? where British General Cornwallis surrendered to George Washington?s colonial army, marking the end of the American Revolution. Our short, meandering ride takes us to the Yorktown Battlefield Colonial National Historical Park and Visitor Center, where we take some time to explore the park. We then make our way to our final celebratory lunch together in a well-known, local restaurant before loading up the van for the drive back to Richmond. All departing flights should be scheduled for 6pm or later tonight. Breakfast and lunch included.

Cycling: 10 miles (1?2 hours, paved road), Elevation gain/loss: +285'/-254'; Van transfer: 1 hour

Gear List

This gear list has been created to help you choose the best equipment for the trip. Try to bring only what is necessary, as this will help you and the field staff. The weather and other conditions at the time of your arrival will dictate what clothing and equipment you will be required to use each day and what (if anything) can be left behind. It may be a necessary precaution that you bring certain items on the list, even if it is uncertain whether or not they will be needed.

Collection of selected R E I Co-op cycling merchandise and snacks laid out to pack for a bike tour

What to pack

Contact Us

Feel free to give us a call at 800-622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales (800-426-4840) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.