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Selected Trips

    Simon Harry

    Simon Harry

    Enthusiastic | Spirited | Engaging

    Mini Bio

    I make a yearly pilgrimage to France to catch at least a few stages of le tour, and have actually managed to get my wife interested. I’m a qualified British cycling performance coach, work as a mountain bike leadership tutor training new guides, and volunteer at my local cycle club. I’ve loved all things two-wheeled since being swept up in the BMX boom of the ’80s and then the mountain bike boom of the ’90s. I love combining my love of cycling with guiding, and it’s so rewarding to take folks to some of the most beautiful parts of the UK. I’ve been bikepacking since before it was called bikepacking. Two years ago, I struck off a bucket list item by completing the French Divide, a two-week self-supported Bike backing race. In 2024, we have the Italy Divide, and then, in 2026, the big one – the Tour Divide in America.

    With my other hat on, I work as a lecturer at my local university, teaching Forestry and Countryside Management. I also don’t mind getting my hands dirty and can build a mean drystone wall.

    Having taken a two year ‘Let’s go to the other side of the world’ sabbatical with my wife-to-be, I headed to New Zealand to live out of a van to get to know the country – the results of which was that on our return, we promptly bought a van, converted it, and travelled extensively on this continent.

    Favourite Place to Play

    Wales and Yorkshire – having family in each area helps!

    Not a lot of People Know This

    I was in two episodes of Dr Who and a Bond film. I have also fought the boxer Joe Bugner (it’s on film!).

    Experience Read More
    • I have been obsessed with bikes since my first BMX (Skyway TA) in 1984
    • I got my first mountain bike in 1987 (a specialized stumpjumper, ahhh)
    • One of the first Qualified mountain bike leaders way back in 1992
    • I have completed Paris Roubaix, Tour of Flanders, and Gent Wevlegem
    • Completed the French divide in 2022
    • Can build and use a pretty good Bow and Drill for fire lighting
    Biggest Adventure Read More

    French Divide 2022 – 2250kms, 35000m of climbing, 80% off road, self supported. One one of 45 to finish out of 152 and only one of 8 to complete it on a gravel bike.

    Specialist Subject Read More

    Bikes, bikes, bikes!
    Also natural history, forestry, and ecology

    What Fellow Travellers Say About Simon

    Simon and Paul were both great as guides. They always had our wellbeing at the forefront of decision making.

    Michael (Mike) Dooley
    E-bike - The Orkney Isles
    Reviewed on 14/10/2024

    All three were excellent - Nikki, Simon and Fin - took great care of us, accommodated our requests, were always cheerful, fun to talk to at meals

    Jane Hoffner
    24WSTM Tailor Made
    Reviewed on 14/10/2024

    Guides were knowlegable and pleasant to work with. I would recommend them. i would request for them if it were possible in the future.

    Kathy Evans
    24WSTM Tailor Made
    Reviewed on 01/10/2024

    Finlay, Simon, and Nikki did a great job! They were fantastic!
    They took great care with us, made sure we had Garmins, bikes, information on the routes. Communication was very good.
    They cheered us on. Made us feel like we could conquer anything.
    Cheers to them!

    Becky Cleaveland
    24WSTM Tailor Made
    Reviewed on 01/10/2024

    I can't gush enough about Paul and Simon. They were clearly knowledgeable about all things bikes. But, they also were just fun to be around. I failed to focus on directions a few times. Paul and Simon made sure to keep me on the right path.

    Stephene Parry
    E-bike - The Orkney Isles
    Reviewed on 09/09/2024

    Couldn’t have been any better. Simon went out of his way to make bikes available for in impromptu sunrise ride. ❤️❤️

    Martha Wales
    E-bike - The Orkney Isles
    Reviewed on 05/09/2024

    Simon attempted to accommodate each of our needs and did very well at it. Paul was knowledgeable about all aspects of the islands, its ruins, history and fauna. Paul kept in line all the time and Simon looked after us. A good combination.

    Michael (Mick) Smith
    E-bike - The Orkney Isles
    Reviewed on 02/09/2024

    Simon and Fin were amazing. They managed to keep things run smoothly and resolve to alternative solutions incase something planned for didn’t work out. They have been a great company and getting to know them is always a pleasure.

    Yousef Al Nafisi
    Road Cycling - Outer Hebrides
    Reviewed on 12/08/2024

    Wilderness has the best guides in the business. Simon and Keith did everything possible to make sure our trip was safe, comfortable, and loads of fun. They were constantly working behind the scenes to make sure we were well taken care of, and their efforts were much appreciated.

    Karen Dean
    E-bike - The Cotswolds
    Reviewed on 07/07/2024

    Simon and Keith were great. They really made our trip effortless and fun for us.

    Eric Hubbard
    E-bike - The Cotswolds
    Reviewed on 26/06/2024

    Simon and Ben were excellent!

    Garmin were OK most of the time...screen a little hard to read with glare. My garmin shot down unexpectedly a few times while I was cycling.

    Joanne St-Coeur
    Road Cycling - The Five Countries Tour
    Reviewed on 10/06/2024

    SIMON & BEN WERE MORE THAN EXCELLENT…. THEY MADE OUR TRIP
    ( and I was not paid to say this)
    They said they had never worked together before and they made sure not to show it. They worked their A$&### off for us. Some of us were very demanding and they just pushed forward. Their support on the ride was always welcomed , be it van support for our breaks or encouragement on the ride. Their operation was clockwork, from the morning debrief , the ride support and hotel transfers. These two superb gentlemen provided us with as much info that they could for the day’s ride but also facts about the countries we were visiting. I would definitely hope that I would have them as my partners on my next tour with you. They were able in such a short period of time, to make us feel special as if we were part of their family.

    Andre Michaud
    Road Cycling - The Five Countries Tour
    Reviewed on 10/06/2024

    Simon and Ben simply were exceptional, as good as any guides I've had on any of my trips and better than most. I would travel with them again in an instant. Please employ them forever!!

    Howard Wiener
    Road Cycling - The Five Countries Tour
    Reviewed on 07/06/2024

    As I have already posted Simon and Ben went above and beyond. Also their individual knowledge of plants, animal, geology, geography and historical background was so much fun for me to learn about.

    Judith Pyle
    Road Cycling - The Five Countries Tour
    Reviewed on 07/06/2024

    As mentioned earlier, Scott and Simon were excellent!!! They were very knowledgeable about the local areas as well as the history. They were amazing bike riders and it helped them go back and forth to constantly be checking in on the other tour members. They were also helpful in making bike adjustments and repairs in a timely manner.

    Rahul Ravel
    Road Cycling - The Grand Tour
    Reviewed on 17/10/2023

    Scott and Simon were very friendly and personable. Their riding prowess and route knowledge was evident. Loved hearing about the routes and the corresponding history and facts.

    Lori Avis
    Road Cycling - The Grand Tour
    Reviewed on 06/10/2023

    Simon and Scott were outstanding guides. Very knowledgeable, attentive, and also very amusing.

    Jill Bobek
    Road Cycling - The Grand Tour
    Reviewed on 04/10/2023

    Simon and Scott were friendly, approachable, knowledgeable and warm. They kept the stories flowing every evening and are great fun. I felt safe with them as guides and they genuinely came across as people who are passionate about their jobs

    Yvonne Neubauer
    Road Cycling - The Grand Tour
    Reviewed on 03/10/2023

    Simon and q did an outstanding job looking after our needs/wants

    Stephen Chappell
    Road Cycling - Outer Hebrides
    Reviewed on 05/09/2023

    We were constantly looked after by our guides,..Simon stood out because he was always checking in, regardless of the time of day. The care was so appreciated by both Simon and Q.

    Pamela Millar
    Road Cycling - Outer Hebrides
    Reviewed on 04/09/2023

    Simon and Dan were the best guides I have ever had and I have ridden in guided tours to Croatia, Bosnia, Montenegro and Spain.

    Gregory Reeks
    Road Cycling - Outer Hebrides
    Reviewed on 08/08/2023

    Simon & Dan are rock stars!! Kind, generous, easy going, interesting, fun good people. Thank you so much to both of them for making this experience as memorable as it was.

    Jeff Faber
    Road Cycling - Outer Hebrides
    Reviewed on 03/08/2023

    Guides were prefect in every way. Simon and Dan went out of their way to be amazing perfect wonderful kind thoughtful helpful marvellous all week

    Samantha Barker
    Road Cycling - Outer Hebrides
    Reviewed on 24/07/2023

    Detailed previously. Very pleased with both caring, professional and often funny guides. Couldn't have dine better.

    Patricia Mulcahy
    Road Cycling - Outer Hebrides
    Reviewed on 24/07/2023

    I cannot say enough about our guides. Simon was kind, supportive, and thorough in setting expectations. He made sure we were always safe. Gave us realistic expectations for what was in store, and cheered me on when I thought I could go no further/higher. He even gave me one final push to help me crest the top of a particularly challenging ascent.
    Simon and Dan were knowledgeable about the areas we cycled through. History, customs, flora and fauna were shared. Really added to the experience.
    And Dan's cheese jokes cracked me up!

    Eve Barringer
    Road Cycling - The Grand Tour
    Reviewed on 31/05/2023

    Both Dan and Simon were great guides. I think they are super assets to the company and make the experience more safe and more fun. I appreciated their kindness, understanding, and lastly their encouragement during the ride. They were patient, empathetic, and genuine people to keep us company during the ride.

    James Faklis
    Road Cycling - The Grand Tour
    Reviewed on 26/05/2023

    Our guide Simon was great, he looked after our every need, he provided sustenance advice and encouragement . He was good company and knowledgeable.

    Peter Morrison
    Self Guided+ Cycling - The Outer Hebrides
    Reviewed on 02/05/2023

    Is there something better than excellent? I have run out of words for telling Simon and Will how good they are as guides. I hope they know how much our group truly appreciates them and all their hard work. They are the benchmark that all professional guides should aspire to. It was their first time on this itinerary and we honestly couldn't even tell. Not even 60mph, falling trees and a bonafide hurricaine threw them - they just quietly made a plan B and it was amazing. They are delightful, thoughtful, intelligent gentlemen and we would be so lucky to travel with them again.

    Karen Dean
    Road Cycling - The Five Countries Tour
    Reviewed on 08/10/2018

    Simon and Will are simply the best guides we have ever experienced and we have cycled all over the world.

    Guy Dean
    Road Cycling - The Five Countries Tour
    Reviewed on 07/10/2018

    Will and Simon are very special to our group. They are part of it, not just our guides but also our friends. Only warm thoughts, big smiles and huge thanks from me.

    Donna Mosford
    Road Cycling - The Five Countries Tour
    Reviewed on 05/10/2018

    Simon and Will could not have done more for us- they thought of everything. When they found out about our Dublin room days later, they were horrified that we hadn't said anything.

    They not only looked after us, they gave us confidence that we could achieve the demands of the trip, and were good company throughout.

    Kerry Davey
    Road Cycling - The Five Countries Tour
    Reviewed on 03/10/2018

    I have never been on a tour with two better guides than Will and Simon. Their thoughtfulness, tirelessness and attention to detail is extraordinary.

    Joan Dean
    Road Cycling - The Five Countries Tour
    Reviewed on 24/09/2018

    Simon's Gallery

    © Simon Harry / Wilderness England

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