Horse Riding in Dresses: The Ridgeway Romp

Tess and Michele in their ballroom dresses in a small town with a pony

When two adventuresses decided it was a good idea to ride “The Ridgeway” in their ballroom dresses, neither had a clue what they were really in for. “You will die,” their saner friends from home told them. One thing was certain, dead or alive, they would be the best dressed ladies on horseback for miles!

Authors: Michele Rumsey and Tess Glanville

You Will Die… (Probably.)

As we struggled up the Ravine, urging the horses against the gushing water with lightning raging above, I began to wonder how we had got here…..And more importantly, if we would live to tell the tale. After all, when we first began to plan our adventure, a ‘friend’ simply stated, “You will Die.”

So how did it all begin? With Ball Dresses! At the time I ran a Riding for the Disabled Centre, and Tess was my Right hand man/woman. Someone had just donated a load of Ball dresses straight out of the 1980’s, and we were wondering how on earth we could make money out of them. Oddly, I had always had a hankering to ride the Ridgeway, a prehistoric trackway in Southern England, running 120 miles in total. Somehow, on a wet, March afternoon, we put two and two together….And decided to ride “The Ridgeway,” wearing the Ball Dresses, to attract attention and donations to our RDA Centre.

Planning to Ride the Ridgeway

The idea grew wings, and we basically spent a frantic few months, planning, getting my ponies fit, and dodging the worst Summer of Storms in History, for a 5 day Adventure that we will never forget. It wasn’t all about us … That part was crammed into looking after the 14 horses and ponies that belonged to the RDA and teaching (not to mention family life, which may have been neglected slightly).

Having decided on the rough plan … Ride the Ridgeway on horseback, dressed in Ball Dresses to raise money, we then had to fill in several gaps. We decided to take my ponies, mostly because they were my ponies and I wanted to do the ride on them, but also because they were younger than the RDA ponies. At that time I had Paddy, who was around 13 years old, a 14.2hh Fell Gelding, and could be described as having a sense of humor!!

I also had Ryscheyed, an 8 year old 14.2hh Arab gelding, a complete drama queen, but bred for the job of long distance riding. This may have been where the comment about our imminent deaths came in, as neither pony was what you would call quiet, or sensible!

How to Be Famous

Next plan….Publicity! To that end, firstly we dressed up, took pictures and sent them to the local free paper. Next thing you know, the local Newspaper, which has quite a large readership was on it. Once it was in print, there was no going back.

Newspaper article about horse riding in dresses for charity alone the Ridgeway
We are famous! Credits: East Anglian Daily Times

Tess started a Blog, we began hacking the boys out anytime we weren’t working and the weather wasn’t throwing thunder and hail at us. We thought we had a lorry from the local riding school and figured we would pick up a driver along the way. We actually started looking at maps and planning routes (around 15 – 20 miles a day), then phoning round for places to stay. Having fallen in love with the Ridgeway from walking some of it (the most touristy route which has nice tracks and Prehistoric Castles), I was surprised to discover it also crossed major Motorways, ran through built up urban areas, and encountered railway tracks. I may have forgotten that we have built quite a lot of towns and stuff since the Stone Age. Not Tess and I, of course, but civilisation in general!

Having annoyed other RDA Centers in the Areas we wished to stay in, we secured accommodation for most of the nights, we were raising money and even spent a whole afternoon choosing which dresses to wear.

We had a couple of Publicity Stunts in the local Area, namely taking a small sweet pony to the nearest town, dressed in… yes those dresses. We also did a Pub Crawl on Horseback (well someone’s gotta do it!), but the least said about that the better… although it’s all in print for posterity!

Tess and Michele in their ballroom dresses in a small town with a pony
Tess and Michele With Bridie. Photo Credits: Tess Glanville

Losing Horsepower

Maybe at this point we thought our planning skills were going ok. We had a few moments along the way with the ponies. Rash had a slight cough, sniffle moment, and Paddy pulled a muscle. The weather never gave us a break. It must have been the wettest, coldest, stormiest Spring ever!

Then disaster struck! The Lorry we were going to borrow fell through, along with its floor it seems. With only about 6 weeks to go we had no transport. We were lent a trailer … better than nothing. BUT. Rash had a thing about trailers. And then there was the logistics about moving a trailer along the route. We still didn’t have a driver. We even considered riding to the next stop, then biking back to pick up the trailer. Tess began a desperate campaign online to find a lorry. We coerced friends into doing radio interviews. We took to begging! That actually worked. We were offered a lorry from a complete stranger, and a friend offered to drive for us. Oh the sweet relief!

All for the Charity

All we had to worry about was a final place to stay. Tess had joined some “Long Distance Riding Groups” by then and began to gather quite a following on the Blog. One kind lady, who was laid up with a broken leg took it upon herself to find us accommodation for the night we had failed. We were already thinking electric fencing, tethering, moving to a foreign country etc.

With all the plans in place we could relax… just kidding. The last three weeks was madness! We were constantly picking up donations such as Hemp Bedding, hay and general supplies. We were lining up interviews from Radio Stations and Newspapers on route. Of course a lot of this was because we were doing it for Charity and we had to raise as much money as possible. We wrote endless lists.

What to Pack

We had a huge packing list for the ponies … Feed, hay, bedding, water containers, buckets, hay-nets, boots, bandages, first aid kit, rugs, tack, grooming kits, sunblock, fly spray… and then spares of everything! First timers mistake I guess. Of course we didn’t use half of it, and we were only going for 5 days. If the worst disaster struck we could have simply loaded up and come home.

For ourselves … Errr … Baby wipes, 2 Ball Dresses each, boots, Very pink jodhpurs, mobile phones, a map, a camera and that was about it. Luckily the Lorry was fully stocked with alcohol. We were told to drink it….And we tried our hardest.

The “Turd”

“The Turd” was the lorry kindly lent to us. Stalled for 4 horses, with tack storage, toilet/shower, dining, kitchen area, tv, heating, … It was HUGE! I had never driven anything this big before. Perfect for the job in hand. We only picked her up two nights before we left. Having somehow got back to the yard, we loaded up the equipment the next day and tried to get a good night’s sleep.

The Adventure Begins

The Day finally dawned. Over-excited is an understatement. Rash wouldn’t load! 3 hours later, Excitement was turning to Exasperation! I mean, we only had to drive for 5 hours to get to the start, then ride 10 miles to the first destination. No Pressure!

We tried him first, we tried him last. Poor Paddy was on and off, on and off. We coaxed, we pleaded, we used food, we growled, we swore…and smoked a lot. Finally I phoned a friend. We knew his problem was claustrophobia, but couldn’t see the solution. That’s what friends are for! Having undone ALL the partitions and slid them back, Rash was finally happy to load into the space designed for 3 large Eventers! Paddy had the tiny gap between the last partition and the ramp … but Rash was too nervous to eat, so Paddy also had two hay-nets!

The Best Back Up Crew

Having picked up Cheryl-the driver, and her dogs, I drove the 5 hours to the start of the Ridgeway at Overton Hill in Wiltshire. The Turd was laid out so all the doors opened into the stalls, so I could watch my ponies in the rear view mirror. Cheryl was much more than just a driver. Not only could she park that Lorry in places people would struggle to get a Smart Car into, she also found unlikely places to meet up with us, cooked for us, got the feeds and hay ready for the horses and was basically the best one-man/woman back-up crew we could have wished for.

And so we eventually arrived at Overton Hill, in Wiltshire. We unloaded the ponies, Paddy took one look at the sheep everywhere and tried to reload himself! Maybe now is the time to mention, Paddy (Brave across country, and head of his herd) was terrified of farm animals. Any and all farm animals … Rash on the other hand freaked at traffic. This may have been the reason for the dire warning of our impending death. On the other hand, I thought they were well matched. One would lead the other??

Time was marching on as we were 3 hours late, so with a quick photo of the start, and a change into those ball dresses, we set off with absolutely no fanfare.

Ladies in ballroom dresses at the beginning of the Ridgeway
Here we Go!! The Beginning of the Ridgeway, Overton Hill, Wiltshire. Photo Credits: Tess Glanville

The First Day

The first 10 miles were mostly uphill, and fairly boulder strewn. And also covered in sheep. Having snorted and spooked for about 5 miles, Pads realized they were more scared of him. He may also have realized it was getting dark, and he had no idea where he was. Tess and I were starting to think 10 miles was quite long, when over the brow of the hill we spied Cold Comfort Farm, our first stop. It wasn’t really called that, but it should have been! Having settled the ponies, showered (yes, there was a shower), we set off to the nearest village for a pint and food. There was a pub. But it was shut. Back to The Turd for crisps (chips) and bed! We were up and about, the next day, excited to be off.

Leaving the stables to go horse riding in dresses on the Ridgeway
All Elegance leaving Cold Comfort Farm … NOT. Photo Credits: Tess Glanville

Day 2: We rode around 20 miles, from Ogbourne St George to Sparsholt Down. This is the part of The Ridgeway that I had walked, the stuff dreams are made of. Except this day turned a bit nightmarish! The first part of the track is great, over the South Downs, apart from the tire tracks of 4WD vehicles. We enjoyed Uffington Castle, an earthworks type of castle near to the Uffington White Horse.

Legend Has It…

We also passed Waylands Smithy, a neolithic tomb, where legend has it if you leave your horse overnight, he will be shod in the morning. Though, we didn’t test this! Then we hit the M4, one of the busiest motorways in Britain. Of course we knew it was coming, but unsure of the crossing. Well it’s not that bad. If your Horse is happy crossing a roaring Motorway on a very small bridge with open railings. Paddy was fine … Rash not so. Luckily the pub beyond the crossing was open, so Tess could calm herself. If I had known what lay ahead i would have bought a bottle of whisky!

Pig Country

It turned out we were in pig country! Paddy’s worst fear. As soon as we came down off the Ridgeway we arrived at a Pig and Cattle Farm. Sadly the Farm we were staying. Paddy made it clear he wasn’t sleeping in a barn with cows, the Lady Farmer made it clear she thought we were totally incompetent. We hid in the lorry and drunk alcopops from the bar, until we were less scared of the pig lady!

We left in a hurry the next day. After another quick adventure, we re-joined the Ridgeway. I have to say, the next 20 miles was a bit boring. Miles and miles and miles of bleak downs. The going was rough. This was Day 3 Sparsholt Down to Streatley.

Horse riding in dresses into the unknown on the Ridgeway
Into The Unknown. The “Turd” is pictured on the right. Photo Credits: Tess Glanville

After what seemed like forever, we came out into civilisation. Streatley on Thames. We had a lovely host and lovely stables. We also had a lovely pub meal.


When we woke up we had a lovely start to Day 4 in rush hour traffic across the River Thames. As we were in Oxfordshire, we had a quaint idea that we would be riding through lots of Villages, and we could stop at a cafe, sit outside holding the ponies while eating bacon butties. Not So. At this point us horse riders are chucked off The Ridgeway, and sent on a detour up The Icknield Way, which has zero signposts! Or Villages! Or Shops. We were starving! We got lost! Eventually at about 4pm, we finally met up with Cheryl for breakfast. At this point, we hadn’t been shopping … so breakfast was extra strong cider!

The Ladies in their ballroom dresses are a little worn out towards the end of their charity ride
A Little Worse For Wear!!!! Photo Credits: Tess Glanville

Luckily we had re-joined the Ridgeway, and were relieved to see the chalky downs again. We only had 5 miles to go to our overnight stop in Lewknor, which is just off another motorway. We had to ride down the slip road (on-ramp) and down some steps, but were oblivious to the dangers.

This was the accommodation, in a private yard, of a friend of a friend of someone who felt sorry for us. It was very posh! We quietly slipped into the village for pub grub, slept, and quietly crept out at dawn to greet the last full day.

Lewknor to Dunsmore

A day of getting lost! We had to go under the M40 in a tunnel. By this time the boys were very laid back ( or traumatized). Then we crossed a very fast main road before getting very lost in the town centre of Princes Risborough. It’s not necessary to go into town! And I really wouldn’t recommend it.

The track we should have taken, leads up into woodland. By the time we had literally slid down a hill into another pub (just in time for lunch), it was becoming normal to tie the ponies up in odd places, while we ate.

Leaving a pub to ride horses in dresses
Always Leaving Pubs! Photo Credits: Tess Glanville

Having got even more lost, hacking our way through a woodland track, and popping out on the lawn of some important MP (Member of Parliament), we finally found ourselves at Dunmore, where a journalist wanted to interview us about the ride, and the impending storms, floods and doom. Is this where we die?

We met up with friends that night (being closer to home), and drank way too much. The final day, Dunsmore to Wendover, dawned with hangovers, black clouds, torrential rain and lightning.

And so we found ourselves battling up a ravine …

If you want to read more stories about riding horses in dresses, check out the book: Ridgeway Romp available on Kindle, for the full shindig!

If You Want to Do Something Similar…

Although the Ridgeway is an ancient track way, it’s not overly horse friendly any more. The going lends itself to mostly walking with the odd trot. There are several major roads to cross, or in fact ride on.

Accommodation for the Ponies along the route was hard to find … Most of ours were just nice people who read the Blog, and offered us a field or stable. I would strongly suggest joining a local Long Distance Riding group on Facebook for all the help you can get. The Equestrian Adventuresses Facebook Group is a good place to start.

We had a brilliant time with so many laughs and mini adventures along the way. If you have ever fancied chucking your horses on a lorry, and going for a 5 day ride… Just do it.

You can read more about Tess and Michele’s equestrian adventure in ballroom dresses on their blog!

riding in dresses on the ridgeway in England for Charity
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Published by Krys Kolumbus Travel

Krystal Kelly is a California girl on a Quest to see every country. She is a professional equestrian adventuress and has worked internationally with horses since 2010. Since then she has worked at professional competition and riding stables in Egypt, Italy, Romania, India and Bhutan! "I love travelling and I love horses and I am very blessed to be able to do both of my passions for a living!" She now has her own company, Krys Kolumbus Travel where she strives to empower women to travel and provides resources, tips and online courses to encourage women to travel SOLO to unique destinations. www.kryskolumbustravel.com www.krystal-kelly.com

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