4.5
(443)
16,145
riders
306
rides
Road cycling around Upton St. Leonards offers diverse terrain within the Gloucestershire countryside, characterized by the picturesque Cotswold hills. This Area of Outstanding Natural Beauty provides varied elevation gains, from gentle ascents to demanding climbs like Cooper's Hill and Nut Hill. The region features a network of roads that traverse ancient woodlands, farmland, and offer panoramic views across the Severn Estuary. Cyclists can expect a mix of paved surfaces suitable for various fitness levels.
Last updated: May 14, 2026
5.0
(1)
132
riders
41.0km
01:49
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
56
riders
28.2km
01:18
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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36
riders
27.0km
01:08
160m
160m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
31
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
31
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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I stick to the black bear in future n tbh dont rate the staff tbh either far more welcoming at the old black bear in Tewkesbury n cheaper to
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Amazing Italian-style ice cream, fresh milk and coffee Opening Times Gelato: Mon-Thurs - 1200-1700 Fri - 1200-1900 Sat & Sun - 1000-1700 Milk Vending: Thurs - 1200-1900 Fri-Sun - 0800-1900
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Great circular walking route - beautiful part of the world!
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The Pilot Inn at Hardwicke offers traditional pub food with a nice view. Open Mon to Thurs 12:00 - 22:00, Fri and Sat 12:00 - 23:00 and Sun 12:00 - 21:00. Food served Mon to Fri 12:00 - 14:30 and 17:00 - 20:30, Sat 12:00 - 21:00 and Sun 12:00 - 19:30.
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A sharp little climb up to the Painswick Road... if you want a real challenge, cross the road and carry on up Green Street... 25% and loose!
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Some very impressive gates to an equally impressive house!
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There are over 300 road cycling routes around Upton St. Leonards, offering a wide variety of options for different skill levels and preferences. These routes are highly rated by the komoot community.
The region is characterized by the picturesque Cotswold hills, an Area of Outstanding Natural Beauty. You can expect varied terrain, from gentle ascents to demanding climbs like Cooper's Hill and Nut Hill, offering significant elevation gains. Routes primarily feature paved surfaces.
Yes, Upton St. Leonards offers numerous easy road cycling routes. For example, the Roadbike loop from Gloucestershire is an easy 27 km route with moderate elevation, perfect for those looking for a less strenuous ride. There are over 100 easy routes available.
For challenging climbs, routes incorporating hills like Cooper's Hill and Nut Hill are ideal. The Green Street Climb – View Down Green Street loop from Gloucestershire is a moderate route that includes notable ascents and rewarding views. The area has 12 difficult routes for experienced cyclists seeking a challenge.
Road cycling routes often lead to stunning viewpoints and natural features. You can enjoy expansive views from Haresfield Beacon and Painswick Beacon, stretching across the Severn Estuary and the city of Gloucester. Many routes also traverse ancient woodlands and nature reserves like Frith Wood and Laurie Lee Wood.
Yes, you can incorporate historical landmarks into your rides. The Short, Steep Rural Climb – Gloucester Cathedral loop from Hucclecote Meadows takes you past Gloucester Cathedral. Other attractions include the distinctive 18th-century Painswick Rococo Garden and the historic Crickley Hill, known for its wildlife and archaeological significance.
Many routes in the area pass through charming villages like Cranham, Painswick, and Matson, which often feature local pubs and cafes. The Gloucester Old Spot Pub loop from Gloucestershire is a popular option that includes a pub stop, offering a classic countryside cycling experience.
The spring and summer months generally offer the most pleasant conditions for road cycling in Upton St. Leonards, with milder weather and vibrant landscapes. Autumn also provides beautiful scenery with changing foliage. While cycling is possible year-round, winter conditions may include colder temperatures and potentially wet roads.
Upton St. Leonards has some public transport links, but options for cyclists with bikes may be limited. It's advisable to check local bus services for their bike carriage policies if you plan to use public transport to reach your starting point. Gloucester, a nearby city, offers more extensive public transport connections.
Parking is generally available in and around Upton St. Leonards, particularly in village centers or designated car parks. Many routes start from locations with accessible parking. It's recommended to check specific route details on komoot for suggested starting points and parking information.
While many routes involve hills, there are easier, flatter sections and quieter roads suitable for families. Look for routes designated as 'easy' on komoot, which typically have less elevation gain and are shorter in distance. The area's network of roads allows for varied options to suit different family abilities.
The road cycling routes around Upton St. Leonards are highly rated by the komoot community, with an average score of 4.5 stars from over 350 reviews. Cyclists often praise the diverse terrain, stunning Cotswold landscapes, and the rewarding panoramic views from the various hill climbs.
Yes, many of the road cycling routes around Upton St. Leonards are designed as loops, allowing you to start and finish at the same point. Examples include the Canal Bridge at The Pilot Inn – St. Laurence Church, Longney loop from Gloucestershire, which is an easy 39 km circular route, and the Gloucester Old Spot Pub loop from Gloucestershire.


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