Holidays
Shropshire Hills Skyline Challenge

Shropshire Hills Skyline Challenge

Challenge walks in Shropshire Hills

3 nights

Aug

Grades 4

3 nights from

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Members

From

£529

Non-members

From

£559

Groups of 10+

or call

020 3974 8865

Part of our all-new HF Holidays Skyline series, this trip is perfect for those that want to take on an exhilarating weekend walking challenge. With the help of an experienced HF Holidays Leader, you’ll hit all the famous highpoints of the Shropshire Hills National Landscape including the Long Mynd, Caer Caradoc, Ragleth, Hope Bowdler Hills and the Lawley. Over the course of two days, we’ll cover a total distance of 25.5 miles (41 km) with 4,530 feet (1380 metres) of ascent and be rewarded with spectacular views of the stunning Stretton Skyline. Take on this thrilling walk for incredible scenery, ancient history, and maximum bragging rights.

What You’ll Love

The sense of achievement from completing this Skyline challenge
Exploring the best of the Shropshire Hills
Discovering the history of the region
Learning about the unique geology of the area
Views over the Brecon Beacons, Snowdonia, and the iconic Stiperstones Ridge
A more personalised experience thanks to small group sizes (maximum 12 people)

What's Included

Comfortable en-suite accommodation in our country house
Cream tea on arrival day
Cooked or continental breakfast every morning
Daily packed lunches
Three-course evening meals, plus tea & coffee
Guided walking with experienced HF Holidays Leaders
All transport to and from walks where necessary

Itinerary

All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take alternative routes or adapt the running order for weather and/or operational reasons.

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Check-in at the hotel is available from 16:00. If you are a member you can arrive at the house from 14:00. Enjoy a complimentary cream tea at 16:30 and meet other guests.

Distance: 13 miles (20.5km)

Ascent: 2,250 feet (680m)

In summary: Leaving the house through Rectory Woods, we’ll follow the lower slopes of the Long Mynd, passing through the famous Carding Mill Valley to reach the quiet and hidden ‘Batch’ valley. The route continues into Jonathan’s Hollow, and upwards to the northernmost end of the Long Mynd plateau. Following the ancient Port Way which runs along the heather-clad ridge of Long Mynd, we’ll pass an ancient tumulus to reach Pole Bank, the highest point on Long Mynd at 516m. On a clear day Cadair Idris is visible to the west with the jagged quartzite outcrops of the Stiperstones ridge in the foreground.

From Pole Cottage, we’ll follow grassy paths across Round Hill and Callow Hill watching out for wild ponies grazing the common land, before descending to the pretty village of Little Stretton. After crossing the A49 which runs through the Stretton Valley, the route climbs steeply up Ragleth Hill to follow another stunning ridgeline with 360-degree panoramic views of the surrounding hills and valleys. Our descent takes us through woodlands on the side of Hazler Hill and down through Snatchfield Valley back to Church Stretton. From the town it is a short ascent through Rectory Fields to Longmynd House.

Distance: 12.5 miles (20km)

Ascent: 2,350 (720m)

In summary: After a short coach journey (5 minutes approx.), we’ll arrive at the start of the second stage of the Stretton Skyline. We’ll ascend past the Gaer Stone and traverse the stunning ridgeline and two cairned summits of Hope Bowdler Hill. A short descent takes us down to the ancient Cwms Lane from which we’ll ascend to the iconic Three Fingers Rock on the southern end of Caer Caradoc.

Hear about the myths and legends of Caractacus as we follow an ancient route to reach the ramparts of an Iron Age hillfort at the summit of Caer Caradoc and be wowed by 360-degree views. Passing Little Caradoc, we’ll descend to the valley floor, contouring the lower slopes of the Lawley. We’ll then ascend the final majestic ridge of the Lawley with its summit marked by a pole and a bird, visible for miles around. The path continues along the ridge southwards before dropping down to Comley and the lower slopes of Caer Caradoc before crossing the valley to reach the village of All Stretton. From here we’ll wind our way along field paths and quiet roads back to Church Stretton and Longmynd House.

Enjoy a leisurely breakfast before making your way home.

Download trip notes

Daily Walk Options

Medium Walks

Long distances in remote countryside and on rough terrain. You can expect some sustained ascents and descents; there may be occasional sections of scree and steep ground.

Accommodation

Longmynd Hotel

For rural calm in the Shropshire Hills National Landscape, the location of this characterful country house is hard to top. Set in a wooded hillside just a short stroll from the market town of Church Stretton (nicknamed Little Switzerland for its picturesque landscape), you’ll be within walking or driving distance of the Stiperstones, Caer Caradoc, Ironbridge Valley of Invention, and the historic towns of Ludlow and Shrewsbury. And then, of course, there’s the Long Mynd itself – an area of registered common land that has been cared for by a group of farmers (the self-named commoners) who have grazed sheep and ponies here for generations.

A warm welcome
We want you to feel comfortable from the moment you arrive. You’ll find a welcome pack in your room with guest registration forms, menus, order forms for dinners and picnic lunches, the Wi-Fi password, and the front door code. Our houses are locked at night, so we recommend noting the Duty Manager’s number on arrival in case of an emergency (or getting locked out).

Evening entertainment

While evening entertainment varies from house to house, HF Holidays Inter-House Quiz night held after dinner on Wednesdays is a weekly staple. Your HF Holidays leader may be around for tips on guided and self-guided waking routes as well as visit-worthy local attractions.

Walks talks
Our HF Holidays walk leaders host guided walking information briefings before dinner on guided walking holiday arrival days. This is followed by a group Walks Talk for information on the following day’s guided walks (held before dinner every evening). Self-guided walking guests are, of course, welcome.

The walking day
Prior to setting off on guided walks, your HF Holidays Leader will run you through a short safety briefing. There’s also an up-to-date weather forecast on display at the house to ensure you have appropriate clothing and footwear. If you choose to do your own walks or are on a self-guided walking holiday, we ask that you please complete an Independent Walker Card each day. These can be found near the Discovery Point in the house.

Check in & check out

You are welcome to check in from 4pm at the earliest. HF Members can check in earlier, from 2pm. On arrival, you’ll enjoy a complimentary cream tea and get to meet your fellow guests, our HF Holidays Leaders, and the rest of the friendly team. Check out 10am.

• 56 well-appointed guest rooms • Exclusive occupancy: 80 guests minimum • Check in from 4:00pm • For members check in from 2:00pm • Free Wi-Fi • Free on-site parking • Boot room and drying room • 2 travel cots & 2 high chairs • Discovery Point offering a wide range of local area maps, route guides, and information for self-guided walks • Books and games to borrow • Licensed bar • Lounges • Garden • Well-behaved dogs welcome on self-guided holidays • Electric vehicle charging point - Please note, you will need to bring your own cables to use this EV charging point

Seasonal dining, tailored for you

Our team of skilled chefs design our dinner menus to showcase the best of each season, from warming winter comfort food to vibrant summer dishes, including vegetarian, vegan and high-protein options. We also source fruit and vegetables within a 40-mile radius of each house, open every break with a Chef’s Special menu inspired by dishes and flavours of the local area, and are able to adapt dishes to suit special dietary requirements.

Welcome Cream Tea

What better way to start your stay than with a cream tea, served fresh on arrival to make you feel instantly at home. A quintessentially English tradition, our scones are baked in-house and served with preserves and clotted cream, providing the perfect opportunity to meet fellow walkers.

A hearty breakfast to start the day

Start the day with a freshly-prepared cooked breakfast and a wide choice from our continental buffet, including hot drinks, juices and fresh fruit. Our team offer a quick and friendly service, leaving you fuelled and ready for your day’s adventures.

Our famous picnic lunch

Our personalised picnic lunches are perfect for a day out walking, ready to enjoy when hunger strikes. Choose from a large selection of fresh sandwiches and salads, freshly baked cakes and snacks, including the ever-popular Freddos chocolate bar! Everything is designed to fit neatly into your rucksack, and all of the packaging we provide is recyclable or compostable.

3-course evening meals

Our à la carte evening menus feature a wide choice of starters, mains, and desserts, made with seasonal ingredients and, wherever possible, herbs and vegetables from our own gardens. Shared around sociable tables, dinners are relaxed occasions, with drinks available to order at the table or from the bar, and a traditional Sunday roast to round off the week.

Since 2022, the £3 million invested so far has established a flagship HF property. A full upgrade of all rooms is expected to be complete by April 2027 with 65% of guest rooms upgraded. Designed with your comfort in mind, Longmynd Hotel has 56 well-appointed guest rooms available in two categories: Classic and Premium.

Classic Rooms are comfortable en-suite guest rooms, ideal for a peaceful night's sleep. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, and shower gel), and a TV.

Premium Rooms are more spacious en-suite guest rooms*. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, body lotion, shower gel), and a 32-inch TV. Extras include bathrobes, slippers.

We love: For more privacy, the lodges have their own terrace.

The Choose Your Room service is available at our UK country houses, allowing you the option of choosing and confirming a specific room for an extra charge of £30 per room. This is subject to availability. Upgrade supplements apply.

Room supplements

Premium single	Premium double/twin	Choose your room
£20 pppn	£20 pppn	£30 per room

*Views and layout reflect each properties unique character and location

For accessibility and assistance information, please contact our expert team on 020 3974 8865 or view the accessibility information online for Longmynd Hotel

View more details View holidays here

More Information

Walks may be changed for safety reasons and are subject to a maximum and minimum number of guests.

Leaders always consider the safety of the group as a whole, and may need to alter or curtail the walk if the conditions dictate. Your leader may refuse to accept a guest where clothing, equipment or behaviour is unsuitable. In the event of a problem all leaders carry a mobile phone, first aid kit, group shelter, spare maps and a compass.

Please note: If you choose to leave the group your leader is no longer responsible for you.

If you have a particular health condition or disability please put this on your guest registration form. This information will be confidential to your leaders and the house manager, but leaders do need to take account of any issues when planning walks. Please carry a copy of these trip notes with you, or note down the contact phone number for your accommodation (details in the travel section) should you need them in case of emergency.

The UK has a famously unpredictable climate so it's best to be prepared for weather that’s sunny one minute and raining the next.  To make it easier, here’s a list of items you should consider packing.  

Essentials 

Suitable footwear such as waterproof walking boots that provide ankle support and good grip 
Waterproof and windproof jacket
Comfortable clothing (jeans & waterproof capes are not suitable) 
Mid-layer(s) to keep you warm. Fleeces make a good choice
Waterproof overtrousers 
Gloves and a warm hat
Rucksack with waterproof liner
Flask for hot drinks  
Water bottle (at least 1 litre capacity) 
Sunscreen 
UV sunglasses

For holidays operating October through to the end of March, please also bring the following on your walks:

spare warm clothing
spare high energy food
head torch and spare batteries
please note for the October to March season your waterproof jacket needs to offer a high level of waterproofing and wind resistance, and a hood. Look for a waterproof jacket with sealed/taped seams and a minimum HH (hyrodstatic head - this is the rating given on waterproof jackets) of 10,000mm+

Recommended 

Several base layers (long-sleeve or short-sleeve) 
Cushioned walking socks to avoid blisters 
First aid kit, including plasters and insect repellent
Sit mat  
Waterproof pouch for valuables 
Rubbish bag (remember to always leave no trace) 
Wallet/purse 
Camera
Walking poles

Carbon Footprint

We see it as our responsibility to minimise our emissions, not just for this year but every year to come. Our work with sustainability experts, ecollective, has enabled us to measure our carbon footprint and create a strategy to reduce the carbon intensity of our product by 5% each year. Our ambition is to be net zero by 2040 – earlier if we can.

Learn more

Reviews

Code: CSCHF-3-

2026

Back to dates

Fri 21 Aug – Mon 24 Aug 2026

Trip Note Download

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Single Price - Land Only

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Non-members

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Single Supplement

Members

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Non-members

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Itinerary: 3 Nights - Itinerary

Trip Type: Challenge walks

All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take an alternative route, or vary the running order for weather and/or operational reasons.

All holidays are subject to availability. Supplements may apply.

Shropshire Hills Skyline Challenge

What You’ll Love

What's Included

Itinerary

Daily Walk Options