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

Holst The Planets and Star Wars Suite
Sat, 23 May at 07:30 pm Holst The Planets and Star Wars Suite

Cheltenham Ladies' College

ENTERTAINMENT MUSIC
The Oceanaires Big Band and Clare Teal
Sat, 23 May at 07:30 pm The Oceanaires Big Band and Clare Teal

Cheltenham Town Hall

MUSIC ENTERTAINMENT
DYLAN NIGHT @ Smokey Joe's, Cheltenham
Sat, 23 May at 07:30 pm DYLAN NIGHT @ Smokey Joe's, Cheltenham

Smokey Joe's Cafe Bar, Diner & Venue

Brighton
Sun, 24 May at 06:30 am Brighton

Marchant's

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
Sunday session \ud83c\udf99\ufe0f
Sun, 24 May at 07:00 pm Sunday session 🎙️

United Services Club

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

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

ENTERTAINMENT
Harry Potter - Studio Tour
Tue, 26 May at 06:40 am Harry Potter - Studio Tour

Marchant's

ENTERTAINMENT
Severn Valley Railway Bridgenorth to Kidderminster & Worcester free time
Tue, 07 Apr at 08:45 am Severn Valley Railway Bridgenorth to Kidderminster & Worcester free time

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

SHOPPING
Wells & The Bishops Palace & Garden
Wed, 15 Apr at 08:15 am Wells & The Bishops Palace & Garden

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

FARMERS-MARKETS
Winchester
Sat, 18 Apr at 08:15 am Winchester

Marchant's

SHOPPING
Dunster & Minehead
Sun, 26 Apr at 07:15 am Dunster & Minehead

Marchant's

TRIPS-ADVENTURES SHOPPING
16 Cotswold Villages tour stopping at Cirencester
Fri, 01 May at 10:00 am 16 Cotswold Villages tour stopping at Cirencester

Marchant's

Dorchester
Wed, 20 May at 07:15 am Dorchester

61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

ART LITERARY-ART
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 SHOPPING
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

What's Happening Next in Cheltenham?

Discover Cheltenham Events