Schedule Tour de Chesapeake 3 Day – coming – tying up loose ends for 2026
Friday, May 15, 2026:
4-8:30 p.m. – Registration and Check-In – Thomas Hunter Middle School, 387 Church Street, Mathews
- Waivers filled out/signed by EACH participant in person
- Pick up Participant packet, pre-ordered merchandise
- TDC merchandise on sale
- Entertainment provided by our local favorite, Shane Norris
- Baked Goods and snacks for sale by MHS After Prom Committee
- Sponsor/Vendor Tables open
PRIVATE BOAT TOURS by Mathews Deadrise Charters – Tour the East River’s historic homes and waterfront, explore the world of oyster aquaculture and even learn how to shuck the Chapel Creek Oyster – Book yours today! Contact Captain Trey at 804-815-6132 or mathewscharters@gmail.com – or – www.mathewscharters.com
10 a.m.-7 p.m. – Mathews Visitor Center AND Local merchants on Main Street keep their doors open late for your convenience – The Cottage and Lily Valentine Antiques offer 20% off! Also visit Cattails, The Vintage Pearl, Gypsy’s Wagon and more! https://visitmathews.com/shopping-in-mathews-county/
Dinner on your own – See Local Eats
Saturday, May 16, 2026
THE RIDE – CYCLIST INFORMATION/ACTIVITIES
7-10 a.m. – Registration/Check-in open (Inside THMS)
6:30-8:30 a.m. – Coffee and pick-up breakfast items will be on sale at the registration area – to benefit THMS SCA (inside THMS)
7 a.m.-3 p.m. – TDC merchandise available for sale – Inside THMS – GET IT BEFORE IT’S GONE!
8:00 a.m. – All Routes open; SAG available; Rest Stops open (wristband required)
9 a.m.-1 p.m. – Farmers Market – located on the Court Green – Fresh veggies, breads, muffins, soup, granola, and more – grown and made in Mathews!
9 a.m.-4 p.m. – WATER TAXI is available from Williams Wharf (Route 614) to Mobjack (Mill Lane 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 please. It is a VERY NICE alternative to Route 14!!!
**Please note: Lunch time is the taxi’s busiest time…you may want to plan to take it earlier or later in the day.
9 a.m. – 4 p.m. – 14th ANNUAL ART deTOUR – The artists of the Art deTour and other Market on Main vendors will gather on Main Street and around The Bay School Community Arts Center to exhibit and sell their fine art and handcrafted works. Live music can be enjoyed on the porch of the Arts Center as well as at the Farmers’ Market throughout the day.
10 a.m.-3 p.m. – TDC merchandise available for sale – Inside THMS – GET IT BEFORE IT’S GONE!
10:30 a.m. -3:00 p.m. – Box Lunch by Mouth of the South Treats and More – Williams Wharf Landing (pre-registration ONLY) located on Route 614, Williams Wharf Road – Outside, plenty of room to spread out – $13.50 – Menu includes your choice of one of the following:
- Option 1 – Classic Chicken Salad Croissant – Scratch-made chicken salad with diced onion and celery served on a buttery croissant;
- Option 2 – Italian Hoagie – Ham and salami with provolone, shredded lettuce and tomato on a shorty hoagie roll, with house dressing served on the side. Condiment packets will be available;
- Option 3 – BBQ Pulled Pork Sandwich – Slow-roasted pulled pork lightly tossed in BBQ sauce on a fresh roll. Includes a side cup of house-made cole slaw; OR
- Option 4 – Mediterranean Salad (Vegetarian) – Mixed greens topped with chickpeas, English cucumber, cherry tomatoes, red onion, black olives, feta, and a light olive-oil herb vinaigrette
All Lunches Served with Miss Vickie’s kettle chips, fresh fruit, a Quaker chocolate chip chewy granola bar, Welches fruit snack, and Assorted Beverages (Coke/Pepsi products, Bottled Water, Gatorade)
11-2 p.m. – Enjoy live music by local bluegrass favorites, The Tidewinders, while lunching at Williams Wharf Landing
For other lunch options, see Local Eats
11:30 a.m.-1:30 p.m. – Neck/Shoulder Massage available at Williams Wharf – $15 for 15 minutes (pay cash on site)
1 – 5 p.m. – Tour dessert by Mathews’ own, Miss Violet Owens at THMS, ride headquarters – Enjoy a slice of her FAMOUS homemade pound cake created especially for this event! *Free for all Registered Full Tour cyclists at THMS. (wristband required)
4-5 p.m. – Ride Recovery Yoga at THMS – FREE to all participants; bring a yoga mat or towel – This will be outside in front of the school weather permitting (if bad weather, it will be inside THMS)
5 p.m. – All Routes Close and Services End
5 – 9 p.m. – SATURDAY NIGHT PARTY AT THE WHARF – Williams Wharf Landing, Rt. 614
FREE ADMISSION AND OPEN TO THE PUBLIC
- Fresh seafood and other options by Mouth of the South Treats and More; Available for purchase on site – this company takes credit cards.
- Cash Bar – Beer and Wine – Cash only please
- Entertainment/Dancing provided by 7th Street, an 8-piece dance band out of Yorktown, VA.
- Shuttle available to/from THMS (no drinks permitted on the bus)
Sunday, May 17, 2026
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.
Breakfast is on your own – try Richardson’s Café, Howard Dooley Cafe, Mathews Grill & Deli, Hardee’s, or Subway.
Visit the Mathews Visitor Center and other local shops along Main Street and beyond – hours vary
PRIVATE BOAT TOURS by Mathews Deadrise Charters – Tour the East River’s historic homes and waterfront, explore the world of oyster aquaculture and even learn how to shuck the Chapel Creek Oyster – Book yours today! Contact Captain Trey at 804-815-6132 or mathewscharters@gmail.com – or – www.mathewscharters.com
Visit “Local Attractions” , “Weekend Activities” , and “Places to Worship” for more things to do for riders or non-riders AND the kids in your group!
