Get ready for a weekend of scenic cycling, waterfront views, local flavors, and small-town charm! The Tour de Chesapeake is back and better than ever, now hosted by the Mathews Outdoor Club – a perfect match for keeping the wheels turning on this beloved tradition.
Haven’t registered? Don’t sweat, we take walk-ups!
To reduce lines at the time of registration, you can download the Walk Up Form and have it already filled out. Walk-up Registration will be held from Friday, May 16th from 4:00 p.m. until 8:30 p.m. & Saturday, May 17th from 7:00 a.m. until 10:00 a.m. at Thomas Hunter Middle School at 387 Church Street, Mathews. Each participant must sign their own waiver.
The Ride – Saturday, May 17
- Multiple route options – all flat, scenic, and relaxing
- Fully supported ride with rest stops and SAG support
- Free on-site camping at Thomas Hunter Middle School (ride HQ)
- Water Taxi from Williams Wharf to Mobjack (blue route) – bikes welcome!
- Pre-ordered box lunches at the Wharf with live music by The Tidewinders
- Homemade dessert reception back at HQ
- Yoga recovery and on-site massages to unwind
- Merch available inside THMS – while supplies last!
Weekend Activities for Riders & Guests
Make it a full weekend in Mathews! Enjoy:
- Kayak Tours with Craven Expeditions (Fri–Sun, 10–3, by reservation)
- Private Deadrise Boat Tours with Mathews Charters
- 13th Annual Art deTour with live music and artist demos on Main Street
- Mathews Farmers Market – Sat. 9 AM–1 PM
- Late-night shopping Friday, open galleries, and historic attractions
- “No Frills” rides on Sunday to explore Gwynn’s Island and Mobjack
- Breakfast and lunch options available throughout the county. Full schedule and details available at tourdechesapeake.org
📣 Help Us Spread the Word!
Follow Tour de Chesapeake on Facebook for updates (especially related to weather!), photos, and last-minute info.
Friday, May 16
• 4pm-8:30 pm – Registration & Checkin
• Book ahead a boat or kayak tour
• 10am-8pm – “Art Speaks Encore Exhibition” @ Bay School Arts
• Shop at the Mathews Visitor Center Mathews Visitor Center and local merchants
• Dinner on your own
Saturday, May 17
• 7am-10am – Registration/Check-in, TDC merch for sale until 3pm.
• 6:30-8:30am – Coffee and pick-up breakfast items
• 8:00am-5pm – All Routes open
• 9am-1pm – Farmers Market
• 9am-4pm – WATER TAXI is available from Williams Wharf
• 8am-4pm – 12th ANNUAL ART deTOUR
• 10:30am-3pm – Box Lunch by Creekside Catering (pre-registration ONLY & live music by the Tidewinders 11am-2pm
• 1pm-5pm – Tour dessert by Central Village Homemakers
• 4-5pm– Ride Recovery Yoga at THMS
• 5-9pm – PARTY AT THE WHARF
Sunday, May 18
• Cyclists are welcome and encouraged to ride on Sunday!! Signage will remain in place until 2:00 p.m.; SAG and rest stops not available.
• No scheduled events this day, but please enjoy all that our small town has to offer – restaurants, shopping, and local attractions!
🎶 Don’t Miss the Saturday Night Party at the Wharf!
Join us in a waterfront celebration to start summer off right! Open to the public! Hosted by the Tour de Chesapeake…that’s why it’s FREE TO GET IN!
Live Music by 7th Street. Seafood and sides available for purchase by Creekside Catering. Cash Bar – Beer and Wine. Bring a chair, your friends and your dancing feet! NO outside food or drinks, no coolers please.
Thank you to our sponsors!
Burton’s Waterfront at Isabell K. Horsley Real Estate
Rappahannock Bicycle Co.
Queens Creek Marina
Johnson Law Center
Lennon Dental Center
Chesapeake Bank
Interested in sponsoring the MOC? All sponsors will be listed on this webpage and on the race premium & event signage. Take a look at our sponsorship page here.
Mathews Outdoor Club 