Winchcombe Way Weekender - Day 2- Eastern Loop - 21 miles

Schedule

Sun May 24 2026 at 08:00 am to 06:00 pm

UTC+01:00

Location

Winchcombe Long Stay car park, Back Ln, Winchcombe, Cheltenham, GL54 5PZ | Cheltenham, EN

Advertisement
Join us for Day 2 - The Eastern Loop of the Winchcombe Way.
The Winchcombe Way is a beautiful 42 mile figure of eight trail with it's centre being in the Cotswolds town of Winchcombe. The trail has been designed to show the highlights of the North Cotswolds and it doesn't disappoint.
Both loops (Sat & Sun ) will start and finish in Winchcombe.
Of course it is up to you weather you want to do both days or just the Saturday or Sunday.
Tickets for this Sunday walk cost £20. This payment is non-refundable. It will only be refunded in the event of a non-weather related cancellation. *Tickets/spaces for this walk/event are pre booked and pre paid, please don't just turn up on the day with cash*
So, on the Sunday we will be doing the Eastern Loop, 21 miles.
2,400ft of elevation.
Highlights include -
Stanton – Often called one of the most beautiful villages in the Cotswolds, with perfectly preserved cottages and hillside views.
Snowshill – A postcard-perfect hilltop village with winding lanes and sweeping views across the countryside.
Stanway – A charming estate village set in a broad valley beneath the dramatic escarpment.
Stanway House – A grand Jacobean manor famed for its towering gravity-fed fountain, one of the highest in Britain.
Winchcombe – A historic Cotswold town full of character, providing a rewarding and well-earned finish to the loop.
Hailes Abbey – Atmospheric medieval abbey ruins set in a quiet valley, once a major pilgrimage site

Please bring plenty of water - minimum 2 ltrs - it's a long day.
Also bring plenty of snacks and a hearty lunch.
Bring layers and check weather the day before.

How to find us -
Winchcombe Long Stay car park, Back Ln, Winchcombe, GL54 5PZ
What 3 Words - ///about.clerk.defender
Advertisement

Where is it happening?

Winchcombe Long Stay car park, Back Ln, Winchcombe, Cheltenham, GL54 5PZ, United Kingdom

Event Location & Nearby Stays:

Icon
Know what’s Happening Next — before everyone else does.
Steven Massey Hiking Tours

Host or Publisher Steven Massey Hiking Tours

Ask AI if this event suits you:

Discover More Events in Cheltenham

Please welcome back Unhooked
Sat, 23 May at 09:00 pm Please welcome back Unhooked

21 Church Street, Cheltenham, United Kingdom

MUSIC ENTERTAINMENT
AIRED SELECTS: May Mashup, 23\/05\/26, Under THE Prom
Sat, 23 May at 10:00 pm AIRED SELECTS: May Mashup, 23/05/26, Under THE Prom

Cheltenham: Under The Prom

Werewolves: An Interactive Gaming Experience
Sat, 23 May at 10:00 pm Werewolves: An Interactive Gaming Experience

Cheltenham Playhouse, 47-53 Bath Road, GL53 7HG Cheltenham, United Kingdom

Cheltenham carboot & market
Sun, 24 May at 07:00 am Cheltenham carboot & market

cheltenham A435, Gloucestershire

The Suffolks May Fair
Sun, 24 May The Suffolks May Fair

The Suffolks Cheltenham

MUSIC FOOD-DRINKS
Circular Knitting Class
Sun, 24 May at 11:00 am Circular Knitting Class

The Kiwi Fruit is Cute, Normandy House, 305-309 High Street, GL50 3HW Cheltenham, United Kingdom

WORKSHOPS
CWGC War Graves Week Tour 2026 - Cheltenham Cemetery World War 2 Tour
Sun, 24 May at 12:45 pm CWGC War Graves Week Tour 2026 - Cheltenham Cemetery World War 2 Tour

Cheltenham Cemetery & Crematorium

NONPROFIT CHARITIES
Tabletop Role-Playing Game: The Musical!
Sun, 24 May at 01:00 pm Tabletop Role-Playing Game: The Musical!

Cheltenham Playhouse, 47-53 Bath Road, GL53 7HG Cheltenham, United Kingdom

LIVE-MUSIC COMEDY
Wellesbourne Market &\/Or Stratford Upon Avon
Sat, 23 May at 08:15 am Wellesbourne Market &/Or Stratford Upon Avon

Marchant's

Winchcombe Way Weekender - Day 2- Eastern Loop - 21 miles
Sun, 24 May at 08:00 am Winchcombe Way Weekender - Day 2- Eastern Loop - 21 miles

Winchcombe Long Stay car park, Back Ln, Winchcombe, Cheltenham, GL54 5PZ

TRIPS-ADVENTURES WORKSHOPS
CWGC War Graves Week Tour 2026 - Cheltenham Cemetery World War 2 Tour
Sun, 24 May at 12:45 pm CWGC War Graves Week Tour 2026 - Cheltenham Cemetery World War 2 Tour

Cheltenham Cemetery & Crematorium

NONPROFIT CHARITIES
Weald & Downland Living Museum
Mon, 25 May at 08:15 am Weald & Downland Living Museum

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

ENTERTAINMENT
London - Museums or shops
Wed, 27 May at 07:15 am London - Museums or shops

Marchant's

WORKSHOPS SCIENCE-FAIR
Royal Air Force Museum Hendon, London
Thu, 28 May at 07:15 am Royal Air Force Museum Hendon, London

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

ART TRIPS-ADVENTURES
Ely
Sat, 30 May at 06:30 am Ely

Marchant's

Short tour stopping at Moreton in Marsh & Chipping Norton
Tue, 09 Jun at 08:45 am Short tour stopping at Moreton in Marsh & Chipping Norton

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

MEETUPS SHOPPING
The Donkey Sanctuary & Sidmouth
Thu, 25 Jun at 07:45 am The Donkey Sanctuary & Sidmouth

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

EXHIBITIONS ART
Sidmouth
Wed, 08 Jul at 07:45 am Sidmouth

Marchant's

ART LITERARY-ART
Kew Gardens & Palace
Sat, 12 Sep at 07:15 am Kew Gardens & Palace

Marchant's

WORKSHOPS

What's Happening Next in Cheltenham?

Discover Cheltenham Events