Haywards Heath
Trail Running Calendar near Haywards Heath 2026-2027
Explore the top trail runs near Haywards Heath for 2026-2027! We've gathered 138 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
A guided 12.5 mile trail run around Box Hill that gains about 1000 metres of elevation across woodland, heathland and open fields. Group pace with technical climbs and scrambling and a chance of an alcohol free beer at the finish.
Three single-loop ultra races of 50k, 55 miles and 100 miles start and finish in Eastbourne, crossing the Seven Sisters and running toward Plumpton. Courses use grass trails, farm tracks and woodland paths on the South Downs.
A 50 km trail ultramarathon from Dorking along the Greensand Way through the Surrey Hills, with a 5 mile loop, marked and supported aid stations, electronic timing and a finisher medal.
A continuous 200 mile winter trail loop around the South of England on the North Downs Way, Vanguard Way, South Downs Way, Wayfarers Walk and St Swithuns Way.
A 100 mile winter point to point trail across the South Downs and North Downs from Amberley Museum to Juniper Hall with a 35 hour limit, three aid stations, crew and drop bag support, medical cover and a strict mandatory kit list.
Mince Pi Run on 13 December 2026 at Shalford Park, Guildford offers looped offroad races from 3.14 to 31.4 miles, a Pi marathon option and a one mile fun run shaped like the Pi symbol. The course runs along the water and results are posted online.
A self-navigated festive night trail of about 5 miles through Friston Forest and downland, with medals, a bar perk and a fancy dress dessert prize.
A dawn to dusk trail challenge at Box Hill where runners complete laps of a roughly 10 mile loop with about 2,400 ft ascent per lap; entries include insurance, medical cover and a finisher medal.
A traditional 3.5 mile Boxing Day run around Hindhead commons and the Devils Punch Bowl, with Mens, Ladies and a Drinking Run category. All profits support Holy Cross Hospital.
January 2027
A challenging 10K trail race on Box Hill with steep climbs, rough trails, a water station at 6 km and a separate children s fun run.
An annual New Year five mile cross country in Penshurst village over rolling hills and woodland trails. Open to ages 10 and above with entry fees supporting Hospice in the Weald and awards across junior, local and canicross categories.
A guided 30 mile trail run from St Martha's Hill exploring the Surrey Hills and Box Hill with an experienced ultra runner and coach. Group pace, recommended 22 miles training, cost £55 and an alcohol free beer may be available.
Running at Bewl Water on 10 January 2027 with 10k, 5k and a junior run on multi terrain routes beside the reservoir; maps and GPX files are provided.
A last-person-standing backyard ultra near Alfriston featuring repeated 4.2 mile loops on mixed trail and farm tracks, token checks, basic aid station and sustainability measures.
A 10‑mile and 5‑mile trail challenge at Pippingford Park with 1568 ft of climbing, hard packed forest trails, wide views and bespoke medals.
February 2027
Guided 10 km trail run around the Devil's Punchbowl in Hindhead, Surrey, with hills, views and group navigation. Events take place at dusk or at night with headtorches and cost £22 per person.
Trail races of 10 Mile, 5 Mile and a junior run take place in Bedgebury National Pinetum & Forest on 7 February 2027. The undulating multi terrain courses can be muddy after wet weather and include a bespoke medal and free photos.