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Top 5 long-distance cycling routes near Winchester


Looking for the best long distance cycling routes in Winchester. Read Jack Martins suggestions. Jack is a keen cyclist who lives in Winchester. Read his article on cycling the south downs. 

Cycling routes near Winchester


There is one obvious popular cycling route that is not on the list. This route is the south downs way. However, due to this route being off-road, I have chosen not to include it in this list.   However, we have covered this route before, and you can learn more about it here. These routes will start and end outside Winchester cathedral, and the GPS route can be downloaded from the links in this blog.    


Old Winchester Hill loop


A trip into the Southdowns is by far one of the most popular routes for weekend group rides, but it also provides a near-perfect location for those dreaded hill repeat interval sessions.

You can take many different roads to get to old Winchester hill, but the following route is a good combination of fast flat roads with quite scenic climbs taking in lots of the local wildlife, and for these reasons, this is my favorites route near Winchester.

Old Winchester Hill is a biological site of special scientific interest in Hampshire, and the top of the hill provides excellent views over the Southdown’s.

As you make your way out of Winchester will soon understand how challenging the hills are in the Southdown’s.   Within the first 10 minutes of the ride, you will ride up the short but steep magdalen hill and the picturesque cheese head. How to improve your cycling by steven robinson. 

The first 10-15 minutes of the ride can be busy during rush hour, so it can be advised that you if you are a novice or are taking kids on this route to avoid rush hour times.


Once you got over Cheese Head, take a right onto Longwood dean and go straight across at the crossroads.


You will now be into the Southdown’s and on smooth wide-open traffic-free roads. You can enjoy the undulating roads down into Warnford before taking a right into west melon and cycling up old Winchester hill.


When tackling the hill, pacing your effort is essential. The route has a series of pitches up to 12% and some false flat phases but make sure you save some energy for the top, where it averages 8% for the last 150 meters.


The road carves its way up old Winchester hill, bending and twisting up the hillside, but there are several views spots along the way, and you defiantly need to stop at least once to appreciate the view.


If you are lucky at the top, you may spot Alan’s coffee van, which serves some of the best coffee in the Southdowns at the top of old Winchester hill throughout the week.


You can take the same roads to get back to Winchester, but I prefer to come back via coombe, East Meon and then the route through West Meon.


Stockbridge coffe lab loop



This loop out to Stockbridge and back is one of my favorites cafe loops for those non-competitive social rides.


This routes also has minimal climbing in it compared to the old Winchester hill route. Starting at the cathedral and riding out of town along Romsey Road before getting on to Stockbridge road can be pretty busy. Common mistakes when cycling long distance.


So this route probably isn’t suitable for young children or absolute beginners. As you ride past Sparsholt, you will pass over several small rolling hills with spectacular views of Crawley Forrest and west wood before reaching upper someone. Long distance cycling tips.


These roads are far quieter but actually larger in width and much smoother, providing the perfect road for group rides. The road remains primarily flat for the next 2-3 miles until you take a right onto Stockbridge road.


Stockbridge is a 1.5-mile climb averaging 3.5 per cent with beautiful smooth tarmac providing an excellent location for that mid group ride strava segment attempt or just a view out over Crawley Forrest.


When you get to the roundabout at the bottom of Stockbridge road, take a left on the mini-roundabout, and you will see the beautiful Stockbridge high street.


During weekdays this sleepy road is home to the small population of the village but come the weekend, the high street is busy with cyclists and all manner of dog walkers and families.


One of my favourite cafes in Stockbridge is Coffee lab which sells some of the best chocolate cake I have ever tasted, and I’ve been readily informed that they make pretty good coffee too.


The route back to Winchester follows the same roads out of Stockbridge (I’m sorry about the 1.5-mile climb after the cafe stop, but there’s no way of avoiding it) and through kings Somborne until you reach Ashley road.


This turning will take you through the short, punchy hills of west wood and to the viewpoint of Farley mount. Some narrow country lanes with breathtaking views of farmers fields follow you all the way back into Winchester town centre.

Back roads to Alresford



This is one of my favourite social routes because it hardly has any hills and is suitable for cyclists of ages and abilities.


The route leaves Winchester via the short sharp hill of magdalen hill before taking a left turn at Fiar lane. Once on fiar lane, it is unlikely that you will see more than 10 cars on your whole ride.


Fair lane is a narrow country lane with breathtaking views of farming fields and the odd dear if you’re lucky. Once you reach Easton, take a right onto Avington park lane and appreciate the freedom that awaits you.


As you go through the quiet country lanes, you will reach Avington park (watch out for the cattle grids as you leave and enter the park), which is home to various wildlife throughout the year, including Highland cattle, sheep and cows.


In the summer, Avington Park provides an excellent spot for picnics and sunbathing with glorious views across the lake to Avington house, a 16th-century English country house.


As you exit Avington park and follow the river Itchen, you will see the Avington park golf course and then pass through Ovington, where there are several pubs.


Take a left turn and cycle for half a mile to reach the historic village of Alresford, which has a variety of independent pubs and cafes.


After stopping at Alresford, I usually go the quicker way back, following the other side of the river, Itchen going through Itchen stoke and Itchen Abbas.


However, if you are taking little kids with you on this route, I would stick to the back roads through Avington as it has less traffic and is a lot safer.


Test valley route


This route may be just a simple out and back course along the same roads, but it is one of my favourite routes because it has everything you need for interval training.


Leaving Winchester and head out towards kings worthy, taking a left onto Lovedon Lane. You will now be on rolling hills with sweeping turns and minimal traffic.


Once you get to stoke charity, take a right turn, follow the road to Micheldever, and take a left. Be careful of farm traffic as you pass through here! Once you’ve ridden through the sweeping bends and rolling hills of Micheldever, head towards Micheldever station and go straight across at the crossroads.


You are now officially in the test valley, and you better have your climbing legs ready because you are in for a lot of really, really steep hills over the next 5-10 miles.


Going over the bridge and taking a right-hander down towards the test bally golf club is usually the fastest part of this route, and it’s easy to hit speeds of 40-45 mph.


However, your speed soon slows down as you ride over Whitehill and into the punchy hills of Overton. If your legs are still feeling good, then you can continue onto the menacing climb that is the warren but be warned, it’s a lot longer and way steeper than it looks.


However, if you aren’t in the mood for the extra hills, now is a good time to turn around and take the same roads back to Winchester, and the good news is that most of the time, it is a tailwind the whole way back.


Off the beaten track towards Andover


This is another out and back route and is really only suitable for experienced cyclists due to small sections of main roads being used on this route.


As you head out of Winchester, join Andover road and go straight across at the road about. This route starts off with fast-rolling hills and wide roads but switches up once you enter the B3420.

From here on in, expect to see tanks, chinooks and other military vehicles as the roads around here are often used for military training by some of the military training camps nearby. The twist and turn following the contours of the rolling hills and the descent down into Hill Farm is a personal favorite, and if you have the confidence, you can reach some very high speeds.


Once you take a left on to Wherwell high street, get ready for one of the most challenging climbs in the area. Once you’ve taken a right at the white lion Inn, you will probably be in your easiest gear for the next 3-5 minutes as the gradient of the road is relentless and only gets steeper.


The road sign only says 8%, but I can assure you that the hairpin and the road after it are more like 12-14%. Whilst the climb may be tricky, on a clear day, the views from the top are more than worth it. 10 tips for planning your first cycling adventure.


You may see some retro single-seater planes landing on the grass airstrips in newton Stacey and Chilbolten down if you are lucky. You can continue after the Wherwell climb and make your way towards Andover, but I usually turn around at this point and follow the same roads back into Winchester.



Useful links


Top 5 long-distance cycling routes near Winchester


Old Winchester hill


Stockbridge coffee lab loop


Back roads to Alresford


Test valley route


Off the beaten track towards Andover



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