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8 Hard Cycling Hills in Gloucestershire

by | May 3, 2017 | Gloucestershire

The Cotswolds and hills go hand in hand, therefore it’s only right that Cyced dedicates an article to some of the toughest inclines in the area. Many of the hills on this list are around the Cheltenham area and are children of Cleeve Hill, the largest in the county. The statistics are taken from the specific Strava segments Cyced created for each climb, so the measurements and categorisations of the hills should be familiar.

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Birdlip Climb

Distance: 0.9 miles | Elevation Gain: 555ft  | Average Gradient: 11%  | Peak Gradient: 28%  | Category: 3 | Strava

With the highest peak gradient on this list, Birdlip Climb is a tough opponent to face. The incline lacks any flat sections, and so there’s no real time to rest and recoup whilst riding. However there are places at the side of the road to pull in if this monster starts to take its toll on you. The climb ends once you break through the trees and enter Birdlip, where you can refuel if you need to. 

Cleeve Hill North

Distance: 1.5 miles | Elevation Gain: 430ft | Average Gradient: 5% | Peak Gradient: 14.9% | Category: 4 | Strava

Cleeve Hill North is located on the B4632, heading from Prestbury/ Southam into Winchcombe. This climb is one of the most ridden in the area, and is host to some fierce competition.  There are plenty of places to rest on the hill, as a pavement is present for most of the incline, and there are several flat sections to take it a little easier on. However, the sections that aren’t flat are challengingly steep. The official Cyced segment ends once you reach the junction for Cleeve Hill Golf Course. 

Cleeve Hill South

Distance: 1.4 miles | Elevation Gain: 349ft | Average Gradient: 5% | Peak Gradient: 13.2% | Category: 4 | Strava 

This climb is the reverse for Cleeve Hill North, but is definitely worth a mention as it boasts as much of a challenge as its cousin, but requires a more tactical approach. Starting just outside of Winchcombe and following the B4632 all the way to the junction for the Cleeve Hill Golf Course, this climb has no places to stop and is more of a steady incline rather than a short burst effort. 

If you’re looking to cycle onto Cleeve Hill and the Cleeve Common, please look through the cycling code of conduct for this preserved area.

Cycle up Cleeve Hill with these Gloucestershire cycling routes

Cleeve Hill Cycling


Harp Hill

Distance: 0.3 miles | Elevation Gain: 412ft | Average Gradient: 9% | Peak Gradient: 16.4% |Category: N/A |Strava 

There are many hills in the Cotswolds that receive the attention of cyclists, but Harp hill is a little less known, and so made it to this list as our underdog. This is the shortest segment here, but offers a quick burst effort as opposed to a long arduous climb. Situated in the Charlton Kings area of Cheltenham, just off of the B4075, Harp Hill is made up of one quick rising incline and a turn at the top of the segment.      

Leckhampton Hill

Distance: 1.6 miles | Elevation Gain: 368ft | Average Gradient: 4% | Peak Gradient: 23.2% | Category: 4 | Strava 

Leckhampton Hill is one of the most notorious leg killers in the Cotswolds. The segment is split into two main inclines with the first being steep and painful, and the second being a long slow rising gradient that finishes you off. There are a few drives to pull into if you’d rather take the climb in two parts, but other than that the road lacks a pavement on the left side to ease your struggle. 

Painswick Climb

Distance: 2.6 miles | Elevation Gain: 476ft | Average Gradient: 3% | Peak Gradient: 16.3% | Category: 4  | Strava

Anyone who has ridden through this area will know why it’s called Painswick.  The Cyced segment begins just after the fork in the road at Pitchcombe, where you will need to follow the A46 Stroud Road. As the longest segment in this list, it supplies around ten minutes of constant struggle, the whole time of which you’ll be screaming at your legs to shut up. The climb itself is a complete contrast to the unique beauty of the Gloucestershire village, which is situated about halfway up the hill and provides the perfect resting opportunity to catch your breath. Don’t let the lower average gradient of this segment fool you, there is enough of an incline over the extended distance to defeat even the most seasoned rider. The Painswick Climb is the very definition of an uphill battle.


Distance: 1.8 miles | Elevation Gain: 559ft | Average Gradient: 6% | Peak Gradient: 19% | Category: 3 | Strava

Snowshill, and Winchcombe Climb, are two infamous hills included in the Wiggle Cotswold Sportive. The climb itself is a little effort to get to if you’re coming from one of the bigger towns in the Cotswolds, but once you reach it, and if you can get to the top, that adrenaline rush will be all the reward you need. This is definitely not one to underestimate; there is very little warning that you are approaching the climb, so it can catch you off guard. The segment starts just outside of Broadway on Snowshill Road, heading towards Snowshill, and ends on the other side of the village. There aren’t many places to stop, but you can refuel in the village if you’re running low of water and food.

Winchcombe Climb

Distance: 1.2 miles | Elevation Gain: 560ft | Average Gradient:  8% | Peak Gradient: 24.1% | Category: 3 | Strava

I’m sure we’ve all faced a monster climb or two in our time, many of you may even have tackled a few on this list, but this hill is just cruel. The segment can be found just outside of Winchcombe, starting at the crossroad for Sudley Castle and finishing at the very top of the hill. The finish is characterised by a hole in the wall on the right hand side, which is a popular place for cyclists to take photos to document their triumph over this beast, but getting there is no easy feat. The first section of the hill is a slow rise, leading into an unforgivingly steep section, which is followed by a false flat for a few hundred meters, which eventually leads to the final incline of the hill. The road is tight and the only places to rest are towards the end of the climb, so clip in tight because you’re in for a long one. 

It’s difficult to say which of these hills is the most difficult, as they each offer a different kind of challenge. Some of the roads that these segments are home to can become busy at peak times of day, so be wary of when you choose to tackle them.

Don’t forget to see the ten best cycling routes in Gloucestershire with our free ebook. Download it here.

 Update 04.05.17 

Aggs Hill

Aggs Hill is a brutal climb. Thanks to our commenter Steven for pointing this Gloucestershire hill out! Just south of Prestbury and North of Charlton Kings, this will get your legs into gear. Wrap round to Whittington and you’ll soon find yourself into the beautiful cotswolds where I can assure you, you will be welcome with more awesome climbs.

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  1. Steven

    You should try Aggs Hill. It’s just after Harp hill and is relentless especially after doing Harp!!! I might be wrong but that may top all of these

  2. Alex

    If you take left up Leckhampton hill onto Hartley Lane it goes up a notch to a level 3 hill. Nice views over the fields too.

  3. Richard Tuck

    The only hill that’s defeated me in Gloucestershire is the lane leading up to Haresfield Beacon. Give it a go in the spring when the roads is wet and muddy and you’ll find your rear wheel spinning on the spot!

    • Arek

      This is tough one indeed. There is Hearfield Beacon climb and two more climbs that can be done in a row if you feel for it – all of them in very close proximity: Both of them starting in Harescombe, first one going Cotswold Way ending nearly same place as Haresfield Beacon climb, second going from Harescombe up to Edge (unnamed road).

  4. Fred Flintstone

    Not to forget Salter’s lane climb near Hailes Abbey, it’s an absolute beast. And Corndean lane from Winchcombe to Belas Knap.

  5. Big Al

    I would give Portway climb a go from Upton st Leonards to join the painswick road – nice short sharp pain.

  6. Nick B

    The 3 other climbs up Cleeve Hill are brutal too- Bushcombe Lane, Stockwell Lane and Gambles Lane, all hit 25% in places. Bushcombe in particular with having you seeing stars by the top of the steepest stretch.


    No Castle Street out of Winchcombe toward Guiting Power on there – I think that is toughest after Aggs. I have not included the feeder lanes onto Cleeve which top at 25%


    Belas Knap short and sharp for sure

  9. Russ F.

    Waterley Bottom climb has a tricky top section, and the surface isn’t helping either. Very narrow lane, if a car comes down the hill you’re probably getting off and not getting back on.

    Similarly steep and tricky, Peak lane joining Frocester hill near the top.

  10. Edward Gibbons

    Good effort, but too many easy gradual ones on this list. Birdlip, Portway and Haresfield are the three serious climbs with Castle Street a tough fourth. Can understand why you missed them off as most people are too cowardly to ride them so Strava activity would send you elsewhere. The climb to Painswick you have is super easy too. There are no tough ones on a county level, but Painswick Rd from Gloucester finishing with the kick to the Beacon is probably the toughest though also riding in and out of the valley in either direction to/from Sheepscombe has seriously steep kicks.


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