Tour de Chesapeake

Mathews, Virginia

Cost: $20-$40, depending on adult or child. Also, cheaper when registering early.

Difficulty: Easy to Moderate. It’s flat, but can be challenging depending on length and wind.

Around Mathews, all roads lead to water.  You will see a lot of it on this ride!  Whatever route you choose will take you off the main road to the nooks and crannies of the area, to the places the residents visit for quiet reflection, fun, and adventure. 

The starting point for all routes is Thomas Hunter Middle School, 387 Church Street, Mathews, VA.  Each route has SAG support, signage, and a Rest Stop with ample food, drink, and potties.

Routes include 23 miles, 30 miles to Gwynn’s Island, 24 miles to Bethel Beach, and 25 miles to New Point Comfort. By combining routes, you can complete your century ride!

Cyclists can take a water taxi — a deadrise waterman’s boat — from Williams Wharf (Route 614 – lunch site) to Mobjack (Mill Land Road) and back.  It can carry up to 6 passengers and their bikes at a time.  The fee (taken at the boat) is $2 per trip per person – CASH ONLY.  “It is a VERY NICE alternative to Route 14”, according to the ride sponsors.  

What’s Included in the above fees:

  • Route Maps
  • Road Signage
  • Full SAG Support
  • Well-Equipped Rest Stops
  • Hot Showers
  • Post Ride Dessert – see below
  • Ride Recovery Yoga 
  • Saturday night Party at the Wharf
  • Bike Repair Support (extra cost may apply)
  • Free Parking (Non-RV)

Tour de Chesapeake’s previous routes. Actual routes may be different this year.