Colonial Virginia

A Bike Tour of Smithfield, Jamestown, Williamsburg & Richmond Virginia

A Bicycle Tour of the Founding of America

Virginia's Lower Peninsula is rich in history:  Home to the first successful English colony in America, the current capital city,  and the incomparable living historic park that is Colonial Williamsburg.  This itinerary also includes Smithfield, Virginia - a picturesque small town on the south side of the James River with lots of heart and much to love!  Bike routes on gently rolling hills and flat terrain connect these sites and more.  Lodge nightly in upscale properties and dine in fine restaurants nightly. 

Book this Tour

Colonial Virginia

Richmond, VA

Tour Difficulty

Mostly Flat, with a few Gentle Hills


6 Days, 5 Nights


Richmond International Airport area

Nearest Airport

RIC Richmond International


From $2825 per person


9/29/24 - 10/4/24 10/6/24 - 10/11/24

Tour Status

Both dates are a go, and both have several spot available as of June 4. Please do not make travel plans until we have confirmed your spot. Enrollment can change quickly.
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Williamsburg is an amazing place, and I'm glad we did some of the recommended readings before the trip. The bike path between Richmond and Jamestown is the best I've ever biked.
Karen, Green Bay, WI

ItineraryDownload Itinerary

Day 1

20–42 miles, mostly flat terrain

After a group shuttle from airport parking at Richmond International Airport, we will all arrive together at Smithfield Station in downtown Smithfield, VA.  We'll have time for bike fittings for renters and a quick lunch orientation.  Afterwards, our first bike ride will take us from the inn to nearby quiet country roads dotted with farms, forest, and creek and marsh crossings.  A couple of distance options are available, as well as strategic van shuttles for any who want more time back in town.  We'll enjoy dinner as a group at a local favorite.

Day 2

20–60 miles, mostly flat

This will be a lovely full day of cycling the country roads in Isle of Wight and Surry Counties.  We will have options for everyone.  One highlight will be a stop at Hampton Roads Winery for wine tasting and a picnic on their lovely grounds, complete with their entertaining "goat tower."  Those who want to get back to Smithfield to do some shopping will have that option.  Downtown Smithfield is a quaint business district dating to 1752, although the first English from across the river in Jamestowne settled the area in 1634.  Multiple museums and art galleries offer a look back at the long history of the area, and you will have an opportunity to find local artwork.  And, you'll want a "selfie tour" with the many local-artist-painted hog statues that are scattered about town.  Smithfield is proud to be the "ham capital of the world."  

Day 3

30–60 miles, mostly flat with a few small hills

After breakfast, it is time to leave charming Smithfield behind.  We pedal more quiet country roads to the Jamestown-Scotland Ferry, which will take us across the James River.   On the way, we will pass the oldest brick dwelling in North America, Bacon's Castle, which is now a state historic site.   Just on the other side of the river, we reach Historic Jamestowne, site of the first successful English Settlement in North America.  Now a very active archaeological site, we will enjoy a talk by one of the expert interpreters employed by Preservation Virginia.   Enjoy lunch, exhibits and monuments onsite afterwards.  A short shuttle or optional more urban bike ride will take us to Williamsburg Lodge at Historic Williamsburg.   We will enjoy dinner as a group in Williamsburg.

Day 4

12–50 miles, a few hills

The historic district of Williamsburg, the second Colonial Capital of Virginia (the first was Jamestown) has been painstakingly restored and replicated over many years by The Colonial Williamsburg Foundation.  Leadership (and money) for this project came from John D. Rockefeller, Jr. and other local and national leaders in the early 20th Century.  Today, we can tour homes, gardens, government buildings and churches in the walkable historic area, and interact with interpreters in period costume.  Passes to Historic Williamsburg will be provided so that you may enjoy the afternoon touring on your own schedule.  We'll move into the Williamsburg Lodge, a beautifully equipped property that is part of Historic Williamsburg. Dinner is "on your own" this evening, with numerous restaurants available within a short walk.   

Day 5

25–61 miles, a few hills

Today is a cyclist's delight!  The Virginia Capitals Trail is a 51 mile, beautifully paved, dedicated bike path traversing the distance from Jamestown to downtown Richmond.  On the way, it passes woods, farms, historic sites, parks and a quaint county courthouse.  As it approaches downtown, the trail slips through a newly revitalized area where we will enjoy lunch and savor the ride.  It is just a mile or two further to our hotel for the final night, located in Richmond's historic Shockhoe Slip neighborhood.  Our final dinner together will be at a fantastic Richmond eatery.


Day 6

3–5 miles, walking tour with some hills

On our final day together, we are going to leave the bikes in storage and enjoy a fascinating guided walking tour of downtown Richmond.  The city has been at the center of Virginia and national history through momentous events and movements.  There is more to see here than we can possibly include, so you will want to consider extending your stay in the area.


$2,825 - $2,925
Bike Rental
Single Room Supplement

Low end of tour price range reflects the 6 month Early Bird Discount.  High end of price range reflects no Early Bird Discount. 

What's Included in Your Tour Price


5 nights at boutique inns and hotels

Included Meals:

Dinners: 3. Lunches 5. Breakfasts: 6; snacks; and hors d'oeuvres most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.

Complimentary Airport Transportation from Richmond

Carolina Tailwinds picks up on the morning of Day 1 and drops off in the early afternoon on Day 6 at the Richmond Airport area (RIC).  Parking will be arranged at an off-airport lot.  Timing formally coordinated 2 weeks prior to tour date.

More details on what's included: 

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View from room at Smithfield Station Virginia bicycle tour

Nights 1 & 2

Smithfield Station

Smithfield Station is a family run hotel, restaurant, marina and shopping complex on the banks of the Pagan River and at the edge of downtown Smithfield.  And short walk takes you into the heart of downtown, where shops and museums await.  Many rooms have balconies overlooking the marina and the surrounding salt marsh.

Nights 3 & 4

Williamsburg Lodge 

Enjoy your stay in a room decorated in fashions drawn from Colonial Virginia–style fabrics, which are vibrant as they are classic—and all of them are nonsmoking. Aside from its cozy atmosphere, the Lodge puts comfort and relaxation in the forefront.  Just steps away from the Lodge are all of the historic buildings of Colonial Williamsburg as well as the restaurants and boutiques of Merchants Square.

Hotel near the Virginia Capital Bike Trail

Night 5

Courtyard by Marriott, Downtown Richmond 

Located in Richmond's historic Shockhoe Slip neighborhood, our hotel is just steps away from the junction of the Virginia Capital Trail and the Canalwalk.



The terrain is a mix of flat terrain, paved bike paths and gently rolling hills, making it accessible to all ability levels.  Road bikes and hybrid style bikes are both appropriate.  

This 6 day tour offers routes of 25 - 50+ miles each day (at your option).  Less ambitious cyclists can take advantage of short cuts and "leap frog" van shuttles along the route to tailor the route to their needs.  

Tour Point of Origin:

Richmond International Airport area.

Getting to the Tour Start (Richmond International Airport)

Driving: Approximate travel distance to RIC--

  • Atlanta, GA:  542 miles
  • Louisville, KY: 568 miles
  • Charlotte, NC: 303 miles
  • Pittsburgh, PA: 340 miles
  • Washington DC:  100 miles

Airports: Richmond International (RIC) is approximately 15 minutes from downtown Richmond.  It is served by most major airlines.

Ground Transit: Taxi, limo, and shared sedan service is available to and from the Richmond airport.

Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Richmond Airport area (RIC).  Pickup timing formally coordinated 2 weeks prior to tour date.

Parking: We have arranged for long term parking there for the duration of your tour.  We will end the tour at the same airport parking area.

Arrival/Departure Timing

Arrival time on the first day of the tour is 9:00 a.m.  Everyone will be shuttled from RIC to Smithfield, VA.  If renting equipment from us, your fitting will take place upon arrival in Smithfield.   Everyone will meet at 12:00 p.m. for lunch and a quick orientation.   Guests will want to meet us at these times dressed in bike clothes, or have them ready to change into them.

On the last day, we plan to get you back to the airport area by 3:00 p.m.  Your return flight should be no earlier than 5:00 p.m. that evening.

Extend Your Vacation

Before or after our activity packed tour, you may want to tack on a few days.  There is a lot to do in and around nearby in Richmond if you have time. 

American Civil War Museum:  Learn about the history of the country’s toughest times exploring the world’s largest confederate collection.

Maymont:  A breathtaking 100 acre estate home to James and Sallie Dooley in from 1892 to 1925.

Virginia Museum of Fine Arts: Admission is free into one of the largest art museums in North America.

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