Olde Worlde England
Tour Dates
21 August 2027 – 30 August 2027 – Price £1990
This departure will be led by Lucy Burnett
The above prices are based on a shared room. The single room supplement for this tour is £495; this option will be available during the booking process.
Ride through the olde worlde heart of the West Country, where golden-stone villages, ancient monuments and rolling countryside make every day feel like a journey through olde England. From Bath to Stonehenge, Glastonbury Tor to Cheddar Gorge, this is a wonderfully varied cycling adventure packed with history, character and beautiful riding.
Cycling

261 miles, 12,975 feet ascent (420km, 3955m)
This tour is a journey through some of the most beautiful and fascinating landscapes in the West Country of England, linking Bristol, Bath, the Cotswolds, the North Wessex Downs, Salisbury, Cranborne Chase and the Somerset countryside. The riding is wonderfully varied, combining quiet country lanes and rolling hills with traffic-free railway paths, canal towpaths and cycleways. Most days are around 30–37 miles, with manageable climbs and plenty of time to ride at a relaxed pace, stop for coffee or lunch and explore the places we pass through. Most of the ride is paved, but there are some gravel sections requiring a recommended minimum 28mm tyre.
Along the way, we’ll pedal through picture-perfect Cotswold villages, ancient woodland and sweeping chalk downs, discover Bath’s Georgian splendour and Roman heritage, and spend time exploring the extraordinary prehistoric landscape around Stonehenge. Further west, the route takes us through the historic towns of Salisbury, Frome and Wells, across Longleat’s magnificent parkland and up to the legendary Glastonbury Tor. The finale is particularly spectacular, crossing the Mendip Hills to Cheddar Gorge before following traffic-free routes back towards Bristol. It’s a tour where the riding is only part of the adventure: every day brings another beautiful landscape, historic town or remarkable piece of England’s heritage to discover.
Highlights
• Bath’s Georgian splendour – explore the honey-coloured crescents, elegant streets and remarkable Roman remains of one of England’s most beautiful cities
• The Cotswolds – ride through quintessential villages, rolling hills and golden-stone countryside, including picture-perfect Castle Combe and Minchinhampton Common
• Stonehenge & Salisbury – discover one of the world’s most famous prehistoric monuments before finishing the day beneath Salisbury Cathedral’s spectacular medieval spire
• Glastonbury & the Somerset Levels – climb legendary Glastonbury Tor, explore the atmospheric town and take in the wonderfully distinctive landscape of the Somerset Levels
• Longleat & the West Country countryside – ride through magnificent parkland and across the rolling hills, quiet lanes and ancient landscapes of Wiltshire and Somerset
• Cheddar Gorge – finish with a spectacular ride through the Mendip Hills and the towering limestone cliffs of England’s most famous gorge
Practical details
Accommodation
We stay in comfortable hotels and high-quality B&Bs on a twin-share, bed-and-breakfast basis. We aim to keep the group together, though occasionally you may be split between nearby properties.
Single rooms are available for a £495 supplement at the time of booking.
Meals
Breakfast is provided by your hotel. Our support team delivers generous, high-quality packed lunches using the best local produce—think fresh sandwiches, bakery bites, fruit and cakes. If the weather turns, we’ll stop at a café instead.
On the road, regular van stops (or occasional cafés) offer hot and cold drinks, snacks, and sweet and savoury treats to keep you fuelled.
Evening meals are not included but are usually enjoyed together in carefully chosen restaurants—though you’re free to do your own thing.
We carry emergency energy supplies, but we recommend bringing your preferred ride nutrition.
(B, L, D) in the Tour Plan indicates meals included: Breakfast, Lunch, Dinner.
Bike Transfers
We make getting your bike to Bristol easy. Free delivery is available from Sheffield to the start and back again after the tour. Simply drop your bike at our Sheffield office before departure, or arrange collection from a convenient motorway service station or other stop en route.
We handle all bikes with care, but recommend you have appropriate insurance, as we cannot accept liability for loss or damage during transport or storage.
Alternative cycling holidays
We offer a wide range of cycling holidays in the UK, to suit all levels of rider. Why not check out some of the following tours, which are also around a week long, and therefore might suit you better than epic rides like Land’s End to John O’Groats!
Scotland End to End (Le Jock!)
We also have a Grade 1 tour in Europe: check out Pedal Nation’s version of the Tour of Flanders in Belgium.
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Starts inBristol
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Ends inBristol
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Road surfacesTarmac (conditions can vary).
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Bike TypeHybrid / Tourer / Road bike
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IncludedOlde Worlde EnglandAccommodationLunchCycling guideGPX filesVehicle supportBaggage transfer
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Not IncludedDomestic flightsEvening meals (unless specified)Bike hireTravel to start & from finishInternational flightsAirport transfersTravel insuranceCookie Policy (US)Cookie Policy (US)Visas
Arrival Day - Bristol
Arrive in Bristol - easily reached by road, train or air - and travel to the hotel. After checking in, you'll have time to get settled and get ready to ride the next day. This evening we will meet for a welcome briefing followed by a group dinner. If you arrive early you might have time for a short self-directed ride along the River Avon - let us know if keen and we will share the route file. Alternatively, there is a lot to see and do in Bristol, including cycling related sights: get in your fill of the more modern and cutting edge before we launch into the Olde Worlde!
Sightseeing highlights
• Explore the Harbourside – wander around Bristol’s historic floating harbour, now packed with museums, cafés, bars and restaurants, with plenty of maritime history along the waterfront.
• Visit Brunel’s SS Great Britain – step aboard Isambard Kingdom Brunel’s extraordinary Victorian steamship and discover what life was like for the passengers and crew who sailed around the world.
• Walk across Clifton Suspension Bridge – take in one of Bristol’s most iconic sights and the spectacular Avon Gorge, then wander around the elegant streets and independent shops of Clifton Village.
• Go in search of Banksy – Bristol is famously associated with the elusive street artist, and exploring the city’s colourful streets is a good way to discover some of the works and neighbourhoods that have made his name.
• Discover Bristol’s creative side – browse the galleries, independent shops and street art around areas such as Stokes Croft and the Harbourside, or visit M Shed to delve into the story of the city and its people.
Bristol to Chippenham via Bath
31 miles, 1,250 feet ascent

Today’s ride takes us deep into the olde worlde heart of England, following a wonderfully varied route from Bristol to Chippenham. We begin on the traffic-free Bristol & Bath Railway Path, following the route of the old railway through leafy cuttings and tunnels before emerging into the beautiful Avon Valley. Over half of the day is on traffic-free cycleways, with just a couple of miles of compacted gravel.
Our route brings us into the magnificent city of Bath, where we will meet the van to exchange cycling shoes for walking footwear. We will stop for a couple of hours here to give you time to explore its extraordinary Georgian architecture and Roman heritage on foot (walking route taking in Royal Crescent, the Circus, Bath Abbey & Roman Baths and Pulteney Weir provided).
But Bath is just one of the day’s highlights: after soaking up the atmosphere, we head onwards along the Kennet & Avon Canal before returning to quiet country lanes and pretty villages. We will stop at a café in historic Corsham and you will have time to wander around afterwards before we continue riding: exploring its picturesque high street with stone buildings that has served as a filming location for Poldark, looking out for the peacocks which roam the streets from nearby Corsham Court and if timings work (12.30 – 3.30pm) visiting the almshouse / schoolroom.
Afterwards, we continue through the Wiltshire countryside to our final destination, the attractive market town of Chippenham. (B, L)
Highlights
• Staple Hill Tunnel – pedal through one of the original railway tunnels on the route
• Bitton Station – a beautifully preserved Victorian station with plenty of old railway atmosphere
• Bath’s Georgian splendour – stroll among the honey-coloured crescents, squares and elegant terraces and discover the remarkable remains of the Roman city beneath the streets of modern Bath
• Pulteney Weir – one of England’s most picturesque weirs, framed by Bath’s historic buildings
• Kennet & Avon Canal – a peaceful stretch alongside this historic waterway, with narrowboats and waterside scenery
• Corsham’s ancient almshouses – a charming glimpse into centuries-old village life
• Chippenham – finish the day in this historic Wiltshire market town
Chippenham to Stroud
32 miles, 1,725 feet ascent

Leaving Chippenham behind and heading into the rolling hills of the Cotswolds, we follow quiet lanes through a landscape of golden stone villages, ancient churches and peaceful farmland. Our first stop is Castle Combe where there is a chance for a wander – down to the bridge to take photos, past the market cross, a chance to nip inside 13th century St Andrew’s church – followed by refreshments at the Old Stables café. As with most days on tour, the pace is leisurely with plenty of stops and time to explore.
From here we continue towards Tetbury, with the riding becoming increasingly scenic as we cross the southern Cotswolds, with some rewarding climbs and wonderful views across the surrounding hills and valleys. We will have lunch in the Veloton café (paid for by us), a special cycle themed café before you have time to walk off your lunch while exploring Tetbury and its medieval steps!
At Cherington we briefly join the Mercian Way, following this long-distance cycle route through the beautiful Cotswold landscape to Minchinhampton. The final miles take us across the open countryside of Minchinhampton Common before descending into Stroud and the Five Valleys.
Here the olde worlde England of the morning meets something rather more contemporary: Stroud is a characterful former wool town that has become a thriving centre for artists, craftspeople and independent businesses, with galleries, studios, markets and a lively creative scene tucked among its historic buildings and old industrial landscape. We will aim to arrive mid afternoon to give you time to explore before dinner. (B, L)
Highlights
• Castle Combe – one of England’s most picture-perfect villages, where honey-coloured cottages cluster around an ancient market cross and stone bridge
• Tetbury – a handsome old market town whose fortunes were built on the medieval Cotswold wool trade. Key sights include the Chipping Steps, Tetbury Market House, the gothic St Mary the Virgin Church and Tetbury Police Museum
• Cherington – a tiny traditional Cotswold village centred around its village green and historic church
• Minchinhampton Common – open Cotswold grassland with wonderful views across the valleys towards the Severn Vale
• Stroud’s creative quarter – discover galleries, artists’ studios, independent shops and a thriving arts scene in this unconventional Cotswold town
Stroud to Swindon
37 miles, 1,850 feet ascent

Albeit our biggest cycling challenge of the tour so far, today's ride also one of the most rewarding. With 37 miles to cover, there’s plenty of time to take the climbs at your own pace, and the occasional steeper gradient is all part of the adventure. There’s no need to race the hills – take them steadily, stop for a breather or even walk a short section if you need to. The reward is a wonderful day of classic Cotswold riding, with quiet lanes, beautiful villages, exhilarating descents and far-reaching views.
We leave Stroud on the wonderfully atmospheric Painswick Old Road, a narrow, twisting lane climbing through wooded hillsides before opening out into the countryside beyond. After checking out the yew trees in the churchyard in Painswick, we continue through the Cotswolds towards Sapperton and the beautiful Daneway Valley. The van will be parked here for refreshments and to give you the chance to swap your cycling for walking shoes during a 2.5 mile wander around the nature trail. Or else you can just relax by the river!
We will detour briefly into both Sapperton and Frampton Mansell villages, which are among the prettiest hereabouts, before continuing to Tarlton and Sout Cerney with an option to detour to the source of the River Thames along the way (not included in mileage – adds about 2 miles including short stretch of busy road). At South Cerney we rejoin the Mercian way through the Cotswalds water park to charming Cricklade – an area of lakes and nature trails created from former gravel pits. We end the day with a traffic-free route into Swindon. (B, L)
Highlights
• Painswick – a beautiful Cotswold village of golden stone, steep lanes and the extraordinary churchyard of ancient yew trees
• Sapperton – a quintessential Cotswold village with strong links to the Arts and Crafts movement
• Daneway Valley – a wonderfully secluded corner of the Cotswolds, with wooded hillsides, old waterways and some fantastic riding
• Frampton Mansell – a peaceful village in the Frome Valley, surrounded by classic Cotswold countryside
• Source of the River Thames – take the optional detour to Thames Head and stand at the beginning of one of England’s great rivers
Swindon to Andover
34 miles, 1625 feet ascent

Today we leave Swindon behind and head into the beautiful North Wessex Downs, where rolling chalk hills, peaceful lanes and wide-open views create a very different landscape from the Cotswolds. From Chiseldon we join a traffic-free railway path, following the route of the old Swindon–Marlborough line through the Wiltshire countryside. The gentle gradients make this a relaxed way to explore the landscape as we head towards the historic market town of Marlborough. We will stop here for a coffee and a wander, taking in the timber-framed buildings on the high street and the twice-weekly farmer’s market. The van will be on hand to transport any purchases (and to purchase local lunch supplies!)
From Marlborough we continue through the peaceful surroundings of Savernake Forest, riding beneath ancient woodland and along quiet country lanes. The route then heads south across the rolling chalk downs, with a series of gentle climbs and descents through the countryside around Great Bedwyn and Vernham Dean before finishing in Andover.
A more relaxed day in the saddle, but no less rewarding, with a wonderful mix of old railway, ancient woodland, historic villages and classic chalk-downland scenery. (B, L)
Highlights
• Chiseldon Railway Path – follow the peaceful route of the old railway through the Wiltshire countryside
• Marlborough – a handsome historic market town on the River Kennet, famous for its broad High Street
• Savernake Forest – ride beneath ancient oaks through one of England’s oldest forests
• Great Bedwyn – a traditional Wiltshire village surrounded by rolling chalk countryside
• North Wessex Downs – enjoy wide views and quiet lanes across one of southern England’s most beautiful landscapes
Andover to Salisbury
33 miles, 1,475 feet ascent

Today is a journey through some of England’s most extraordinary ancient landscapes, as we leave Andover behind and cross the rolling chalk country towards Amesbury and Stonehenge. The route takes us through the open countryside around Grateley and Cholderton before arriving in Amesbury, one of Britain’s oldest settlements. From here we enter a landscape shaped by thousands of years of human activity, with Stonehenge and Woodhenge providing two remarkable glimpses into prehistoric Britain.
We will gather in Amesbury for coffee before giving you 3 hours of independent time to explore Stonehenge and Woodhenge (entrance fee to Stonehenge not included). The van will be parked in the visitor centre car park with picnics.
After exploring this extraordinary corner of Wiltshire, we regather in the Woodhenge car park, leave the open downs behind and follow the River Avon through the peaceful Woodford Valley, passing through Upper and Lower Woodford and a succession of quiet rural lanes. Our final historical flourish is Old Sarum, where an Iron Age hillfort, Norman castle and the remains of Salisbury’s medieval city occupy the same atmospheric site. From here we descend into Salisbury itself, with its magnificent cathedral providing a spectacular finale to a day spanning thousands of years of English history. We will aim to arrive in time to visit the Cathedral before returning to our hotel. The city itself is stunning for an early evening wander. (B, L)
Highlights
• Amesbury – one of Britain’s oldest settlements, at the heart of the Stonehenge landscape
• Stonehenge – encounter the world’s most famous prehistoric monument in its vast chalk downland setting
• Woodhenge – a mysterious prehistoric monument of timber posts, just a short ride from Stonehenge
• Woodford Valley – peaceful lanes and pretty villages following the River Avon through the Wiltshire countryside
• Old Sarum – explore the atmospheric remains of an Iron Age hillfort, Norman castle and medieval city
• Salisbury Cathedral – finish beneath one of England’s most spectacular medieval spires in this beautiful cathedral city
Salisbury to Frome
37 miles, 2,100 feet ascent

We leave Salisbury behind and head west today through the beautiful countryside of Cranborne Chase and the western Wiltshire Downs. The route quickly leaves the city behind, following quiet lanes through rolling chalk hills and peaceful villages before reaching Barford St Martin and continuing towards Fonthill Bishop. It’s a day of big views, winding country roads and some rewarding climbs, with the landscape becoming increasingly rural as we head towards the Somerset border.
At Fonthill Bishop we will stop for a coffee at the highly rated Riverbarn café. We then pass the Fonthill Arch and beneath the old railway line through an atmospheric tunnel before continuing through Hindon and across the rolling countryside towards Kingston Deverill and Maiden Bradley. We will have a picnic lunch in Kingston followed by an optional 2 mile wander up to the trig point on Cold Kitchen Hill for expansive views. You will be provided with a gpx file for this and instructions but it will be self led.
The final section takes us through the magnificent Longleat estate and its sweeping parkland before we continue into Somerset and on to Frome. Here we finish in one of the West Country’s most characterful towns, with its medieval streets, historic buildings, independent shops, galleries and lively creative scene. (B, L)
Highlights
• Cranborne Chase – sweeping chalk downs, wooded valleys and wonderfully quiet country lanes
• Fonthill Bishop – a pretty Wiltshire village surrounded by beautiful countryside and the historic Fonthill estate
• Fonthill railway tunnel – pass through an atmospheric old railway tunnel as the route heads towards Hindon
• Kingston Deverill & Maiden Bradley – peaceful villages tucked among the rolling Wiltshire and Somerset countryside
• Longleat – ride through one of England’s grandest estates, with its magnificent Elizabethan house and expansive parkland (option to visit house and maze, ticket not included)
• Frome – explore the atmospheric old streets, independent shops, galleries and creative spirit of this historic Somerset town
Frome to Wells
33 miles, 1,625 feet ascent

The great riding just keeps coming, as we continue through the beautiful Somerset countryside, leaving Frome behind and heading towards the historic town of Shepton Mallet where we will stop for a coffee and the chance for a wander. And that’s all before reaching one of the most evocative landscapes in England. Rising dramatically from the Somerset Levels, Glastonbury Tor has been a place of pilgrimage, legend and mystery for centuries. From the top, there are wonderful views across the surrounding countryside and, on a clear day, a real sense of just how distinctive this corner of Somerset is. The van will meet us at the bottom of the hill with shoes and a picnic to enjoy from the summit!
After taking in the atmosphere of Glastonbury via a cycle loop around the town, we join the traffic-free EV1 for a peaceful final stretch towards Wells. The route follows quiet lanes and cycleways through the Somerset countryside, bringing us to our destination beneath the magnificent cathedral. After so many days exploring the olde worlde landscapes of southern England, Wells makes a wonderfully fitting place to spend our final night before returning to Bristol. We will go straight to the cathedral before the hotel to give you a chance to visit it before closing. The medieval streets provide wonderfully atmospheric evening wandering.
Nb the route can also be shortened by riding straight from Shepton Mallett to Wells and a gpx file and support will be provided for this option.
Highlights
• Shepton Mallet – an ancient Somerset market town with a fascinating medieval past and historic streets
• Glastonbury – climb the iconic Tor, explore the atmospheric ruins of Glastonbury Abbey and wander the wonderfully eccentric historic town, steeped in legend, pilgrimage and folklore
• Somerset Levels – enjoy views across the flat, watery landscape surrounding Glastonbury, in striking contrast to the hills we’ve crossed
• EV1 – follow a peaceful traffic-free route through the Somerset countryside towards Wells
• Wells – arrive beneath the magnificent cathedral in England’s smallest city, ready to explore its medieval streets and historic heart
Wells to Bristol
28 miles, 1,625 feet ascent

Our final day is a spectacular finale, taking us from the medieval splendour of Wells into the Mendip Hills and the dramatic landscape of Cheddar Gorge. We climb through the hills via Wookey Hole and Priddy, with the road steadily gaining height before reaching the top of the gorge. If you are weary from the previous days of riding you can either rest up here or ride down through the gorge and get a lift back up (numbers dependent – might need to be shuttled). Alternatively, you can enjoy one of the great rides of the tour: a thrilling descent through the towering limestone cliffs of Cheddar Gorge, followed by the climb back up the way you have come!! (not included in mileage or ascent because this would push the holiday into a different grade, but 100% worth the effort). Depending on everyone’s decisions, we we will take a chance to explore the gorge and enjoy coffee in Cheddar itself (and the chance for a wander to buy some cheese!)
With the biggest drama behind us, we leave the Mendips and head towards the peaceful waters of Chew Valley Lake for lunch. The final miles are a gentler affair as we follow the traffic-free EV1 towards Bristol, bringing our Olde Worlde England adventure to a satisfying conclusion in the city where our journey began. If we arrive early, there is the option of an extra short loop along the river cycle path – or a well deserved drink or coffee to celebrate arriving! (B, L)
This evening we shall head out into Bristol for a celebratory dinner.
Highlights
• Wookey Hole – pass through this atmospheric Mendip village, famous for its spectacular limestone caves and underground river
• Priddy – a beautiful Mendip village surrounded by open limestone grassland and ancient landscapes
• Cheddar Gorge – ride through England’s most spectacular gorge, with towering limestone cliffs rising dramatically on either side
• Cheddar – explore the village at the foot of the gorge, home of the famous cheese and surrounded by the dramatic Mendip landscape
• Chew Valley Lake – enjoy the peaceful waters and open countryside as the tour begins its final approach to Bristol
Departure day
Today you are free to enjoy breakfast and to check out in your own time, before making your way home. In the meantime we will transport any bikes back to Sheffield or drop-off points en route. Or else why not add a few days to your trip and enjoy what Bristol has to offer? Just ask and we can add a few days on to your hotel booking. (B)
