Gwynn’s Island Festival Race

4m Run, 10m Ride or Run/Ride Duathlon

2021 June 26th starting at 7am

Held in conjunction with the annual Gwynn’s Island Festival on the last weekend in June, with options for runners and cyclists.

Gwynn’s Island in Mathews County is the host site of this annual festival. Join runners & riders in this unique tour of one of Virginia’s special locations – then hang around to enjoy the charming island festival. 2021 registration will close when 200 participants have signed up OR on June 19.

Our local school athletes ability to train and compete has been seriously impacted by the recent health crisis – along with their ability to organize fundraising activities. Our club receives support from these local athletes and their parents during our events, and is paying back with cash and equipment donations. The race director for the Gwynn’s Island Race has selected the local athletes as the recipients of this event’s proceeds. The Gwynn’s Island Civic League (festival hosts) receive a donation as well every year.

Consider Sponsoring the Gwynn’s Island Race. Your support of the Gwynn’s Island Race will significantly enhance our donation to these student athletes by helping us defray the cost of hosting such a large event. The race organizer is an IRS 501c3 recognized charitable organization so your donation is tax deductible – Tax ID will be provided on your donation receipt.

Race Details
4 mile road run

Starting and ending adjacent to the festival grounds, the route follows quiet backroads around the island, behind the local fire station, by the small rural post office, and alongside a wharf side dock. The race course is 4 miles and the cost is $30. For those looking for a shorter distance, we will have a Free Fun Run open for everyone (distance just > 1 mile).

10 mile bicycle ride

Weaving around the backroads of Gwynn’s Island, you’ll catch glimpses of the Chesapeake Bay, Milford Sound, and the popular campground & RV resort on the island as you complete the course. The route is 10 miles and the cost is $30.

Combine the run & ride

Feeling adventurous? Sign up for the combined Run & Ride and make it a duathlon. The 4 mile run and 10 mile ride routes are the same as the individual events described above – you’ll stage your bicycle so that as you complete the run leg, you can immediately head out onto the bike course. The cost is $50.

Race day start times

Please see the important COVID-19 information below. The run & ride will go “on” unless there is a major weather event – the start times and post-event activities are subject to change depending on current Virginia guidelines for group social activities. Unless stated otherwise, the Duathlon (Run/Ride Combo) and the 4 Mile Run at 7:00am, the 10 Mile Ride at 7:05am and the Fun Run at 7:10am.


All event participants will receive a commemorative t-shirt and finisher medal. Top finishers in the run, ride and combo will be recognized along with age group categories for each event. Back by popular demand: the Solar Power Hula Dancers!


The health & safety of event participants, spectators, volunteers and community residents are top of mind as we plan & prepare for our events. Check back to this section for the latest adjustments to this event in response to Virginia state guidelines. Important to note: the Gwynn’s Island Festival Run/Ride will proceed on the date scheduled barring any weather-related disruptions. The start times and post-event activities may be subject to change as noted here. Direct email communication will be sent out to registered participants as well.

January 1, 2021 Update. As of this date, registration for the Gwynn’s Island Run/Ride will be capped at 200. Participants may start in waves depending on the current Virginia state guidelines. We continue to monitor the restrictions on group gatherings and will adjust/adapt our start & finish areas to comply.

Other EVENT Facts
4-Mile Race Course

Start/Finish at Gwynn’s Island Civic Center > Old Ferry Road > Chesapeake Rd > Mad Calf Rd > North Bay Haven > Old Ferry > turnaround at Tin Can Alley > Old Ferry > South Bay Haven > Edwards Landing > turnaround at dock > South Bay Haven > Old Ferry to finish.

Mathews County Visitors

Learn more about the area by visiting the Mathews Visitor Information website at which also includes a full calendar of events and recommended places to eat & stay during your visit. The Gwynn’s Island Museum is just one of the county’s historic sites and sits right next to the festival grounds.

Places to Stay in Mathews

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