Gloucester County
Walking Events Calendar near Gloucester County 2026-2027
Monthly updates for Gloucester County
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Gloucester County for 2026-2027! We've gathered 28 great walks in the area. Check out our detailed list below to find your next local walk.
August 2026
Walkers may choose 5K, 10K, or 13.1 Miles, starting at 850 Jolly Pond Rd, Williamsburg, with limited water at lap ends and the finish alongside running races.
September 2026
Walkers can choose a 1 Mile Fun Walk or a 3.1 Miles 5K, following roads parallel to Jamestown Rd with a Landfall turnaround and finishing in the meadow across from Jamestown Settlement. Dogs allowed on leash; no retractable leashes and water for..
Walkers can choose 5K, 10K, or 13.1 Miles, starting at 850 Jolly Pond Rd in Williamsburg on a clear course with limited water at lap ends and no EMS on site.
Walkers can choose 5 km, 10 km or 13.1 miles on a clear local road course starting at 850 Jolly Pond Rd, Williamsburg, with limited water at lap ends and no EMS on site.
A family friendly 5K walk on the Mariner's Museum certified course, from E Boundary Rd (Williams Field) across from Warwick High School. Race day packet pick up and parking at Warwick High School are provided; proceeds benefit Transitions Family..
The event offers walking on paved cart paths at The Hamptons Golf Course on a 4.4 mile loop, with 5 hour and 11 hour options and parking plus aid stations at the clubhouse.
Walkers can choose a flat road 5K or 1 Mile route starting at the Fire Dept on Mark Pine and finishing at Buck Rowe’s Store Museum through the storied Guinea region.
October 2026
Walkers can do 5K, 10K, or 13.1 Miles from 850 Jolly Pond Rd Williamsburg on a marked course with limited water at lap ends and minimal staff.
Walkers follow a 3 Miles out and back course across the tree covered Williamsburg Landing campus beside College Creek, with the William A. Doig Health Club and Spa as the start location. Parking is at Laurel Lane Elementary with shuttles and ligh..
Walkers follow a 10 km out and back route starting at Chickahominy Riverfront Park that crosses the Chickahominy River Bridge and returns via the well maintained Capital Trail. The walk is a walking only event held alongside the 10K run.
Walkers can join the community 5K along City Center for 3.1 Miles, starting at Tradition Brewing Company, 700 Thimble Shoals Blvd in Newport News. Registration is $5 and each entry includes a raffle ticket and a post walk gathering at the brewery..
Walkers can choose 5K, 10K, or 13.1 Miles routes from 850 Jolly Pond Rd in Williamsburg; water is limited to lap ends and finish and EMS is not on site.
Walkers can do a 5K on a flat, fast course through Governor's Land between Two Rivers in Williamsburg. The start is at 2711 Two Rivers Road and the walking entry has a registration fee of $30.
Walker friendly 2.215 mile loop in Williamsburg VA on crushed gravel, mainly flat scenic trail with porta potties and food; full loops count toward 50k and half marathon.
Competitive 3.1 Miles walk starts and ends near Amblers House, 2205 Jamestown Rd, on a flat scenic route via Jamestown Island and the Virginia Capital Trail. Walkers must keep one foot on the ground; awards, race T, medal and refreshments provide..
November 2026
Walk options include a 10 km race walk, a 5 km walk and a 1 mile Healthy Hike, all based at 101 Mounts Bay Rd, Williamsburg. The course is the paved Carters Grove Country Road through the county complex, with parking and same day packet p..
Walkers can choose 5K or 10K routes starting at Lois Hornsby Middle School, 850 Jolly Pond Rd, Williamsburg. The event is low pressure and local, with limited water at lap ends and the finish and no EMS on site, so walkers should plan for wea..
Walkers follow a 10 km route from 180 Lakeview Drive, Toano VA on a 1.05 mile trail loop with woods and water views on flat dirt. Bodyweight strength stations include modifications, with light refreshments and a four hour cutoff.