Trail Running calendar near Henley-on-Thames 2025-2026

Run the festive Christmas Jubilee River Run 2025, a pop up six hour event on a flat 5.24 mile out and back along the Jubilee River with views toward Windsor Castle. Places are limited and every finisher receives a bespoke medal.

Join the 20th Christmas Pudding Dash in Pett near Hastings for festive, family friendly cross country races across farmland and woods. Multiple distances, medals, prizes and mince pies make this muddy, fun run a great seasonal tradition.

Join the Chelmsford Brew Co 12ks of Christmas for a festive 12k trail from the Voodoo Keller Bar to the brewery and back, finishing in the town bar. Expect drinks, a Santa hat and prizes for the best Christmas fancy dress.

Celebrate the season at the Slow and Dirty, a family friendly trail race along a converted branch railway near Sturminster Newton, with a level 19k course or 11 mile option. Scenic Stour Valley running, dogs and buggies welcome.

Take on Winter Wanderlust, a 50 km trail ultramarathon along the scenic North Downs Way from Detling to Wye. Enjoy rugged chalk downs, three well stocked checkpoints, hot food and a finisher medal for those who make the cut.

Enjoy the Soup Run, a friendly 6 mile multi terrain social run on hilly trails around Bembridge, starting and finishing at the community centre. Entry includes a souvenir, warming soup and roll and a prize draw ticket.

Celebrate early with The Early Christmas Present, a timed loop along the peaceful Stroud Waterways canal where you can run from 5k up to ultra on flat towpath. Limited places, bespoke finisher memento and virtual entry available.

Join the Festive Friston Forest, a five mile night trail through Litlington woods and downs on 22 December 2025. This friendly timed adventure features festive fancy dress, a finisher medal and a pint or hot drink back at the pub when you r..

The Die Hard Christmas Marathon and Half Marathon is a festive running event taking place on December 24, 2025, at Caldecotte Lake in Milton Keynes. Participants can choose between a full marathon, consisting of 7.5 scenic laps, or a half m..

Join the Santa Claws 10km, a festive winter multi terrain cross country run at Renegade Brewery on the Yattendon Estate on 24 December. Expect muddier trails than the summer event, a canicross option and a finisher medal plus a beer or alco..

Run on Christmas Day along the Thames at the Christmas Day Cracker Run, a 7 hour time challenge where you choose laps from a 3 km minimum to ultra distances. Finishers get a medal and festive food and treats at race HQ.

Join Pitsea Running Club for the Crown to Crown Boxing Day 5k, an upbeat off road loop through Willow Park starting and finishing at Westley Heights Country Park. A friendly community race perfect for festive miles and post Christmas fun.

Winter X is a scenic trail running day from Meonstoke with routes along the South Downs Way. Distances from 10km to 70km, with checkpoints, chip timing, marshal support and a finisher shirt.

Tackle a scenic 7.5 km off road loop along the 1066 Country Walk past Farbanks Henge and finish by The Plough Pub. Entries are limited to 50 runners with post race tea and cake and prizes for first male and first female.

The Christmas Charity Run at Rathfinny The event takes place on 28 December 2025 at Rathfinny Wine Estate, The Tasting Room, Alfriston, Polegate, BN26 5TU. The run is limited to 75 places and is open to local runners only. Part of the entry..

Join the Layer Twixmas Trail on 28 December for a self guided 5 to 6 mile trail run around Layer de la Haye. Enjoy a Twix, hot drink and cake, optional festive fancy dress with a cash prize and dog friendly fun.

Take on a scenic 10 mile cross country through Hainault Forest with Ilford Athletic Club, three undulating laps across tracks and grass. Friendly club atmosphere, limited entries and post race prizes make it a rewarding winter challenge.

Tackle an undulating winter cross country on Sunday 28 December 2025 at Acresford Sand and Gravel in Huncote, featuring Croft Hill and a stream for a scenic but testing 10K. Junior one and two lap races share the same start and finish.

Join the Gingerbread Run on 28 Dec for a festive 5 mile off road farm run near Swindon with muddy tracks, small hills and a halfway prosecco station. Enjoy an edible gingerbread medal, post run treats and support local charities.

Tackle a scenic, hilly winter 12.5 mile run near Warminster on 29 December and support the Royal British Legion Poppy Appeal. Expect brisk, changeable weather, bespoke finisher medal and a friendly community atmosphere.