Virginia's Colonial Williamsburg Bike Vacation

October 26-31, 2025

Jamestown, Yorktown, and Colonial Williamsburg

Join us in October as we bike through history, exploring Virginia’s Historic Triangle – Jamestown, Yorktown, and Colonial Williamsburg. Each town played an important role in English Colonial rule in America, for it was in 1607 that the English first landed in the swampy marshes of Jamestown, and then 174 years later the British were defeated in the Battle of Yorktown (1781), the final major battle of the American Revolutionary War.

Our bike trip is based in Colonial Williamsburg, which in the 18th century was the capital of the Colony of Virginia – Britain’s largest and wealthiest colony in the New World. The entire old-town-area has been “frozen in time” and preserved as a living history museum portraying colonial Virginia on the eve of the American Revolution. Everyone remains in character 24 hours a day – shop keepers, townsfolk, children at play, marching militia, tavern folks, political figures, slaves – depicting the days, months, and years leading up to and during the Revolutionary War. Enjoy lots of open-air theatre, visit trade shops, and dine at 18th century taverns. Come, be part of the story, on your 21st century bicycle!

2025 Tour Dates

Oct. 26-31 Book Now

Rave Reviews

GBT provided the best possible experience of Williamsburg… biking, restaurants, picnics, lodging, and activities. They made it so pleasant that all I had to do was enjoy every moment. Judy Q.

Tour Cost

2023 tour cost was $2,995 per person (based on double occupancy)
Single supplement of +$675
2025 tour cost still to be determined

Level of Difficulty

Easy to moderate – 15-40 miles/day, with total mileage of 95-175. 60+ miles of paved bike paths. No big hills, although mileages are longer. Cycle at your own pace. Get a lift in the van whenever you like. E-bikes available (limited supply).

2023 Tour Dates

Oct. 22-27 Book Now

2024-25 Tour Dates

Late Oct. Learn More

Rave Reviews

GBT provided the best possible experience of Williamsburg… biking, restaurants, picnics, lodging, and activities. They made it so pleasant that all I had to do was enjoy every moment. Judy Q.

Tour Cost

$2,995 per person
(based on double occupancy)
Single supplement of +$675

Level of Difficulty

Easy to moderate – 15-40 miles/day, with total mileage of 95-175. 60+ miles of paved bike paths. No big hills, although mileages are longer. Cycle at your own pace. Get a lift in the van whenever you like. E-bikes available (limited supply).

Highlights

  • Explore Colonial Williamsburg, America’s largest living-history-museum
  • Enjoy 60+ miles of paved bike paths throughout the week
  • Unpack only once, by staying at the Williamsburg Lodge the whole week
  • Dine at historic 18th century taverns, with servers in costume
  • Cycle through history at the Colonial National Historic Park, run by the National Park Service
  • Witness America’s beginning during your private guided tour of Jamestown Settlement, a living-history-museum depicting the story of America’s first permanent English colony
  • Cycle the newly-completed Virginia Capital Trail, a paved bike path that connects Jamestown and Richmond – traversing 400 years of history
  • Cycle on quiet country roads passing cotton and tobacco fields
  • Sip wine at the Williamsburg Winery, the largest winery in Virginia
  • Marvel at General Washington reviewing his troops, complete with cannon salutes and fife & drum marching bands
  • Enjoy optional activities such as a sailing trip aboard Yorktown’s 105-ft Alliance tall ship

What’s included?

  • 6 days of cycling and other activities
  • 5 nights lodging (Williamsburg Lodge in downtown Williamsburg)
  • 10 meals (5 breakfasts, 2 lunches, 3 dinners), catering to all dietary needs
  • Free use of our bikes, plus helmet, rear rack bag for your personal items, rear safety light + triangle, water bottle, and T-shirt. E-bikes available
  • Superior level of support throughout your stay (each trip comes with two 15-passenger vans and three professional bike tour guides)
  • Ride with GPS navigation (using your own phone) or paper route notes
  • Exclusive GBT activities, including a private walking tour of Colonial Williamsburg and an evening theatrical show
  • Admission to the Colonial Williamsburg Historic Area, Jamestown Settlement, and Jamestown Island and Yorktown Visitors Centers
  • Full access to our online photo gallery with photos/videos from your trip
  • Small group size of 15-20 people (or organize your own private trip)
  • Pickup and drop-off in downtown Richmond, or at the Richmond International Airport (or nearby hotels)

Highlights

  • Explore Colonial Williamsburg, America’s largest living-history-museum
  • Enjoy 60+ miles of paved bike paths throughout the week
  • Unpack only once, by staying at the Williamsburg Lodge the whole week
  • Dine at historic 18th century taverns, with servers in costume
  • Cycle through history at the Colonial National Historic Park, run by the National Park Service
  • Witness America’s beginning during your private guided tour of Jamestown Settlement, a living-history-museum depicting the story of America’s first permanent English colony
  • Cycle the newly-completed Virginia Capital Trail, a paved bike path that connects Jamestown and Richmond – traversing 400 years of history
  • Cycle on quiet country roads passing cotton and tobacco fields
  • Sip wine at the Williamsburg Winery, the largest winery in Virginia
  • Marvel at General Washington reviewing his troops, complete with cannon salutes and fife & drum marching bands
  • Enjoy optional activities such as a sailing trip aboard Yorktown’s 105-ft Alliance tall ship

What’s Included?

  • 6 days of cycling and other activities
  • 5 nights lodging (Williamsburg Lodge in downtown Williamsburg)
  • 10 meals (5 breakfasts, 2 lunches, 3 dinners), catering to all dietary needs
  • Free use of our bikes, plus helmet, rear rack bag for your personal items, rear safety light + triangle, water bottle, and T-shirt. E-bikes available
  • Superior level of support throughout your stay (each trip comes with two 15-passenger vans and three professional bike tour guides)
  • Ride with GPS navigation (using your own phone) or paper route notes
  • Exclusive GBT activities, including a private walking tour of Colonial Williamsburg and an evening theatrical show
  • Admission to the Colonial Williamsburg Historic Area, Jamestown Settlement, Jamestown Island and Yorktown Visitors Centers
  • Full access to our online photo gallery with photos/videos from your trip
  • Small group size of 15-20 people (or organize your own private trip)
  • Pickup and drop-off in downtown Richmond, or at the Richmond International Airport (or nearby hotels)

BOOK YOUR TRIP (or request more information)

Join us in October as we Bike Through History. We only offer one exclusive departure for this trip, so contact us soon if you wish to be part of this special event.

Great Bike Tours

3282 Mt. Philo Rd,
Charlotte, VT 05445

Have any questions? Contact us!

(802) 777-2009

As Featured In

Trip Advisor Awards Great Bike Tours

BOOK YOUR TRIP (or request more information)

Join us in October as we Bike Through History. We only offer one exclusive departure for this trip, so contact us soon if you wish to be part of this special event.

Great Bike Tours

3282 Mt. Philo Rd,
Charlotte, VT 05445

Have any questions? Contact us!

(802) 777-2009

As Featured In