Chepstow
Walking Events Calendar near Chepstow 2026-2027
Monthly updates for Chepstow
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Explore the top walking events near Chepstow for 2026-2027! We've gathered 23 great walks in the area. Check out our detailed list below to find your next local walk.
August 2026
Walkers follow a relaxed, music filled 5K through Newport, starting and finishing at banc coffee & records, with mobile speakers, no pace pressure and post event music and coffee.
September 2026
The event offers walkers 5k and 10k routes based in Charlton Hayes, family friendly and open to all abilities.
October 2026
At Box Recreation Ground walkers can do the 800 m colour loop (1 or 2 laps) or 5 km signposted trail through grassy Bybrook valley; marshalled, refreshments and toilets
Suitable for walkers on 5k, 10k, Half Marathon, Marathon or Ultra, using 2.5k laps on a tough offroad course at Pengethley Manor Ross on Wye with a hill, vineyard ups and a 7 hour limit.
November 2026
Walkers cover 2 laps of the scenic lake at Parc Bryn Bach, Tredegar; the course is wheelchair accessible with parking, changing and refreshments, virtual entrants record 5km.
December 2026
The event offers walking distances 5k, 10k, Half, Marathon and Ultra. Offroad 2.5k laps at Pengethley Manor Ross on Wye with hill and vineyard ups and downs and a 7 hour limit.
The event is suitable for walkers and offers 5k, 10k, Half Marathon, Marathon or Ultra on a tough offroad 2.5k lap course within Pengethley Manor, Ross on Wye, with a 7 hour time limit.
Walk options 5k, 10k, Half Marathon, Marathon or Ultra at Pengethley Manor, Ross on Wye on a tough offroad course of 2.5k laps through vineyards, 7 hour limit.
The event offers walkers 5k, 10k, Half Marathon, Marathon or Ultra on tough offroad 2.5k laps at Pengethley Manor with vineyard hills and a 7 hour limit.
Walkers can choose 5k, 10k, Half Marathon, Marathon or Ultra on a tough off road 2.5k lap course at Pengethley Manor, Ross on Wye with vineyards, a hill and a 7 hour limit.
Walkers may choose 5k, 10k, Half, Marathon or Ultra on a tough offroad course of 2.5k laps at Pengethley Manor with a hill and vineyard sections and a 7 hour limit.
Walkers can choose 5k/10k/Half/Marathon/Ultra on a tough offroad course at Pengethley Manor Ross on Wye with hills, vineyard ups and a 7 hour limit.
Walkers can choose 5k, 10k, Half Marathon, Marathon or Ultra on a tough offroad 2.5k lap course at Pengethley Manor, Ross on Wye with a hill, vineyard sections and a 7 hour limit.
Walkers can choose 5k, 10k, Half Marathon, Marathon or Ultra on a tough offroad loop at Pengethley Manor Ross on Wye; laps are 2.5k with a hill and a 7 hour time limit.
Walkers can choose 5k, 10k, Half Marathon, Marathon or Ultra on a tough offroad 2.5k lap course at Pengethley Manor with a hill and vineyards, 7 hour limit.
January 2027
Walkers can choose 5k, 10k, Half Marathon, Marathon or Ultra on a tough offroad course at Pengethley Manor, Ross on Wye, with 2.5k laps, hills, vineyard undulations and a 7 hour limit.
Walkers can choose 5k, 10k, Half Marathon, Marathon or Ultra on a tough off road loop at Pengethley Manor, Ross on Wye with a hill and vineyard laps, plus free parking, tea and coffee, sandwiches and toilets.
May 2027
Walkers can choose 100 km (Talgarth to Abergavenny) or the 100 mile loop from Abergavenny on Welsh trails including Offa's Dyke and Beacons Way with aid stations.
Walkers can choose 2.5k, 5k, 10k or 15k at North Somerset Showground Bristol on a 2.5k lap of inflatable obstacles with music zones and an on course water station.
Walkers can choose 3k or 5k routes starting and finishing on the seafront beach next to Revo Kitchen, on a fairly flat course over sand, the Promenade and the Grand Pier. Refreshments and toilets are available; the site is not wheelchair acce..