West Wight Chilly Hilly 2025: The Isle of Wight Legendary Community Run

Freshwater is bracing itself once again for the annual West Wight Chilly Hilly, scheduled for Sunday 14 December 2025, a ten-mile winter plod that claims to be “invigorating” but is more honestly described by regulars as “alarming in places”. The run begins and ends at the West Wight Sports & Community Centre in Freshwater and raises funds to support the centre’s community programmes, swim facilities and wellness activities. Enthusiastic locals insist it’s the perfect way to “shake off the winter fog” which, if we’re being truthful, is really shorthand for “a perfectly acceptable excuse to eat mince pies at 10.15am”.

Three of the Island’s more unusual residents have now emerged from retirement to “support” this year’s runners. Officials did not formally approve their involvement, but it turns out mythical creatures are adept at ignoring laminated signs.

THE FRESHWATER GORGON: DEADPAN GUARDIAN OF THE START LINE
The Freshwater Gorgon has confirmed it will once again be stationed at the start and finish area. It has lived in Freshwater since 2022, blending in with the locals by developing a strong interest in weather complaints, bin collection days, and pretending not to know what day it is.
The Gorgon enjoys the Chilly Hilly for the simple reason that it “requires no participation”, and last year turned only one marshal to stone, “by accident”, after being startled by a poorly timed cowbell.
Runners have described Freshwater’s opening section of the route as “beautiful” and “full of personality”. What they usually mean is:
“I’m pretty sure the Gorgon watched me warm up. I’m hoping it was the Gorgon. If not, I’m not sure what I saw.”
The creature does not interfere unless startled, so race organisers advise participants to avoid sudden lunges, jazz hands or comments about humidity.
Locally, the Gorgon can be spotted near The Piano Café (Totland Road, Freshwater), where staff have grown used to the sound of ceramic cups lightly cracking whenever the creature sighs. They report it is a decent tipper, although “eye contact is discouraged”.

THE ALUM BAY PEGASUS: DRAMA WHERE DRAMA IS NOT REQUIRED
Alum Bay’s Pegasus has announced, with considerable flair, that it intends to “oversee the cliffside miles” again this year. The creature’s retirement has been spent largely preening near the coloured sands and heavily implying that it was once worshipped. Visitors regularly mistake it for part of a theatrical installation.
According to the Pegasus, the Chilly Hilly route is “a sweeping odyssey of mortal bravery across the ancient bones of the earth”. According to runners, it’s “windy, muddy, and the bit near the Needles is a fair old climb”.
Reviews from past years say things like “spectacular views” and “stunning cliff paths”, but what many actually mean is:
“The wind nearly lifted me into the English Channel and something with wings kept circling overhead doing spoken-word poetry.”
After the run, Pegasus is usually found sulking at The Needles Landmark battery cafe because the chefs refuse to “char-grill bacon and cheese toasties with a celestial flame”. Staff say it often recites long monologues about destiny while waiting for its food.

THE TOTLAND BIGFOOT: LARGE, SHY, AND PERPETUALLY BETRAYED BY FOOTWEAR
Totland’s Bigfoot is expected to patrol the wooded sections near Totland Bay and Headon Warren, although “patrol” may be generous; it mostly hides behind trees and tries not to be seen. The creature’s long-standing grievance is the complete absence of footwear in size “prehistoric”.

Bigfoot attempted to join a Couch-to-5k group recently but quit after discovering jogging shoes do not come in “Hulk width”. Runners may hear heavy breathing or see trees gently swaying. This is not an omen; it’s simply Bigfoot attempting encouragement without startling nervous participants.
Totland’s section of the run is often described by finishers as “peaceful”, “serene”, or “very pretty indeed”.

What they usually mean is:
“I heard something snort behind me and decided not to investigate.”
After each Chilly Hilly, Bigfoot wanders down to The Waterfront Bar & Restaurant (Totland Bay) for chips. The staff say it sits outside, facing the sea, pondering where a creature is expected to buy socks in this economy.

WHY THIS EVENT MATTERS
The Chilly Hilly is one of the Island’s most beloved winter traditions, raising money for the West Wight Sports & Community Centre and attracting entrants from seasoned runners to enthusiastic walkers who just want a medal and a socially sanctioned pastry.
The route delivers everything West Wight is known for:
• dramatic cliffs
• woodland valleys
• beaches
• chalk hills
• unpredictable weather
• and this year, several mythical beings with questionable volunteer training
Most importantly, it brings footfall into Freshwater, Totland, Alum Bay and Colwell Bay at a time when local businesses really feel the winter dip.

HOW TO ENTER
Registration is open now via the West Wight Sports & Community Centre. Early booking is advised — the race often sells out due to its reputation for combining lovely scenery with mild peril.

Event information and booking: (HIT THE BUTTON BELOW)
https://westwight.org.uk/events/chilly-hilly/

The run takes place
Sunday 14 December 2025

beginning at West Wight Sports & Community Centre, Freshwater, PO40 9XH.