Cyclists will return to the flat roads and scenic views of Mathews County this weekend to take part in Saturday’s 27th annual Tour de Chesapeake.
The Mathews Outdoor Club event will welcome cyclists from around the state and beyond for a weekend of cycling, local eats, music, “and nice, down-home folks to help with whatever is needed,” a Tour de Chesapeake release stated.
The county will welcome cyclists on Friday evening for check-in and registration at Thomas Hunter Middle School from 4 until 8:30. Entertainment will be provided by Mathews’ own Shane Norris. TDC jerseys and 2026 Tour T-shirts will be on sale as well as a large variety of event merchandise. Several vendors will be on site as well, including After Prom, the P. Buckley Moss Gallery and others. Main Street merchants will be open late for shopping.
Cyclists may also check-in and register on Saturday morning from 7-10.
The supported ride will take place from 8 a.m. to 5 p.m. Saturday, which includes maps, route signage, SAG (safety vehicles), and fully-stocked rest stops provided by the Mathews Rotary Club, Gwynn’s Island Civic League, Scout Troop 1651 and the Bay School Community Arts Center.
There are four concise routes throughout the county each starting at Thomas Hunter Middle School, which will once again serve as event headquarters. The routes take cyclists to Mobjack, Bethel Beach, New Point Lighthouse, the Glebe and Gwynn’s Island, totaling over 100 miles.
The Middle Peninsula Amateur Radio Club and the Mathews Sheriff’s Office will provide security and emergency management on all the routes during the event.
Homemade breakfast items by the THMS SCA and FCCLA will be on sale for cyclists at THMS on Saturday and box lunches by Mouth of the South Treats and More will be offered at Williams Wharf. Lunch entertainment will be provided by another local favorite, William Earl Sadler.
Neck and shoulder massages by Heartfelt Touch Massage will be available for a small fee at Williams Wharf from 11:30 a.m.-1:30 p.m. and THMS from 2:30-4 p.m. Ride Recovery Yoga is offered by Lisa White at THMS from 4-5 p.m. and a “celebration” dessert of Violet Owens’ famous pound cakes will also be provided to all registered cyclists at THMS from 1-5 p.m., both for no charge.
Trey Sowers of Mathews Deadrise Charters will be offering Boat Tours on the East River on Friday and Sunday and will man the Water Taxi for cyclists traveling between Williams Wharf Landing and Mobjack on Saturday.
“The water taxi has become one of the most popular attractions at our event,” said Smith. “Where else can cyclists get shuttled to the next route on a beautiful Chesapeake Bay deadrise?”
On Saturday evening, a Party at the Wharf will be held at Williams Wharf Landing from 5-9 o;clock. This event is free and open to the public. Mouth of the South will be on site offering fresh seafood and more. A cash bar will be available and entertainment will be provided by Lynda Smith and the 7th Street Band. A shuttle will be offered from THMS to Williams Wharf all evening.
The Bay School Community Arts Center will showcase local artists at its Main Street location and the P. Buckley Moss Gallery, located on Poplar Grove Road, will feature special Open House hours throughout the weekend.
Cyclists are encouraged to ride on Sunday on their own; maps and route signage will remain available until 2 p.m.
“There are so many parts to this event and I truly appreciate everyone who works together to make it happen,” Smith said. “I want to thank the locals for your patience and kindness and for helping to keep everyone safe. I hope to make it a fun weekend for cyclists and locals alike.”
This year’s tour is presented by Candace Segalini of Southern Trade Realty, Lennon Dental, Riverside Walter Reed Hospital, Queens Creek Marina, Mathews Visitor Center, M&M Building Supply, One Man Liquor Stand, and Mathews Economic Development Authority.
“We couldn’t do this event without these wonderful sponsors who believe in providing healthy, affordable activities for the whole family to enjoy,” event director Lynda Smith said.
For more information or to register for the tour, visit www.tourdechesapeake.org. If you would like to help with the event, contact Smith at tourdechesapeake@gmail.com.

