Island Running: Gwynn’s Island

Thank you Caryn. You know who you are… Caryn is a recent visitor to Mathews County who reached out to the MOC for recommended running routes. After sending Caryn some of my personal faves, it struck me: this request cannot be unique. When I travel, I also search my destination area for safe & peaceful-looking routes to run, I consult the various exercise apps, or do like Caryn and see if there is a local club with recommendations. That led me here – blogging about Mathews area routes – and if you enjoy these, you have Caryn to thank.

I’m starting this blog series with Gwynn’s Island, which is on the list of “6 Virginia Islands That Everyone Should Visit” – and sits at the end of Cricket Hill Road (VA Rte 223). Curious about the Cricket Hill name? Well, here is a little more information about its Revolutionary War era history. You’ll see this sign as you approach the bridge over Milford Sound which leads you on to Gwynn’s Island. Cricket Hill Road becomes Old Ferry Road (VA Rte 633) once you cross the Milford Haven bridge.

Most Mathews County routes, including the majority of those on Gwynn’s Island, are out-and-back because the roads end at the waters edge. There is at least one 1.25 mile loop on the island that you can incorporate into your own trek. I’ll start off describing the longer distances; all of these courses can all be extended by adding several together to make your own custom island run.


SIX MILES out-and-back. Park at Hole in the Wall restaurant, pictured above, which is the first parking area on the right after you arrive on the island. This parking area also supports the county boat launch so take note of which parking spaces are designated for the restaurant only. Exit the parking lot to the right on to Old Ferry Road (VA Rt 633) and run past several island landmarks, pictured below. After passing the Gwynn’s Island Museum, Old Ferry takes a right turn after which you’ll see the Gwynn’s Island Baptist Church on the left and the Civic Center on the right.

Continue along Old Ferry Road past the Fire Station & the Gwynn VA Post Office (zip code 23066) until Old Ferry Road intersects with Buckchase Road (VA Rte 740) and turn right. The intersection will show another not-so-proud landmark: Tin Can Alley which is a very short dead end lane with countless ‘no parking signs’ (see image below). Tin Can Alley is a sore subject for island residents. As the island’s only public beach access, it became a contentious issue between some late-night beach goers and the residents who live right there. As a response to years of dispute, Mathews County posted the signage.

Buckchase Road leads to Gwynn’s Island RV Resort, where you’ll reach the 3 mile turnaround point to retrace your path back along Buckchase & Old Ferry Roads to Hole in the Wall.


FOUR & 3/4 MILES includes the 1.25 mile “Mad Calf Turnaround” loop! This one starts & finishes at the Hole in the Wall Restaurant and follows Old Ferry Road. Approx 2 miles in, turn left at the Gwynn Post Office (North Bay Haven Rd VA 636) to the end, then left onto Mad Calf (dirt & gravel road) to the end. Cross the wooden footbridge (see photos below) and then turn left onto Chesapeake Road. At the Fire Station (intersection of Chesapeake and Old Ferry Roads), turn right and follow Old Ferry Road back to Hole In the Wall restaurant.

FOUR MILE ROUTE for the Annual Gwynn’s Island Festival Race starts and ends at the Gwynn’s Island Civic Center on Old Ferry Road. During the festival (4th weekend in June) the Civic Center has designated parking in the field near their building. Otherwise, limited parking is available at the Gwynn’s Island Baptist Church (not on Sunday mornings). Exit the Civic Center circular driveway to the right and take the first left onto Chesapeake Road (at the Fire Station. Follow Chesapeake Rd to the wooden footbridge on Mad Calf Road (see pictures above) and turn right and cross the footbridge. Mad Calf Road (dirt & gravel) ends at North Bay Haven – turn right onto North Bay Haven and continue to Old Ferry Road, Gwynn VA Post Office is at this intersection.

Turn left on Old Ferry Rd to the end and U-Turn at Tin Can Alley (see picture above – with all of the ‘no parking’ signage). Retrace the route on Old Ferry Road back to the Gwynn VA Post Office and turn left on South Bay Haven Road. Follow South Bay Haven to Edwards Landing and turn right – see pictures below. Go to the dock and U-Turn back out along Edwards Landing Road, then left onto South Bay Haven, then left onto Old Ferry Road back to the Civic Center.


THREE MILES to the campground. And last but not least, a three miler from the Civic Center to the Gwynn’s Island Campground & RV Resort, which is another out-and-back that can be added onto if desired. Click on this interactive map for the route, along which you’ll see most of the landmarks pictured previously in this blog. I hope you enjoy – look out for more of my favorite routes in Mathews County. When the weather warms up, I’ll be adding my favorite cycling routes as well!

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