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Road cycling routes
United Kingdom
England
West Midlands Region

Oswestry

The best road cycling routes around Oswestry

4.7

(9)

729

riders

66

rides

Road cycling around Oswestry offers diverse landscapes, from quiet country lanes winding through rolling farmland to routes alongside tranquil canals and challenging climbs into hills. The region, situated on the border of England and Wales, features varied terrain including well-paved surfaces and some unpaved segments. Cyclists can explore scenic vistas of Shropshire and Wales, with routes often incorporating historical landmarks. The area provides options for both relaxed rides and demanding ascents.

Best road cycling routes around Oswestry

  • The most popular…

Last updated: May 1, 2026

5.0

(1)

8

riders

#1.

Ostwestry to Ellesmere Lake loop via Whittington Castle

63.6km

02:44

360m

360m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Popular around Oswestry

Cycling around Oswestry

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MTB Trails around Oswestry

Tips from the Community

Walk The Walk 🌳
June 7, 2025, Chirk Tunnel

Chirk Tunnel is a canal tunnel near Chirk, Wales. It lies on the Llangollen Canal, immediately northwards of the Chirk Aqueduct. It is 421 metres (460 yd) long and has a complete towpath inside. The tunnel is claimed to be the first in Britain to have a towpath running through it (along with its shorter neighbour, Whitehurst Tunnel). However, Berwick Tunnel on the Shrewsbury Canal was open by 1797 and included a towpath throughout its 970-yard (890 m) length. As the tunnel at Chirk is completely unlit, a torch/flashlight is necessary for anyone walking through the tunnel, as it is pitch black in the centre. A wooden handrail along the entire length prevents walkers from falling into the canal.

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Friendly pub and hotel. Good food good price

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samzy
April 6, 2025, V20 Coffee

New coffee shop in Ellesmere, really good coffee and good parking for bikes infront of the cafe.

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Cypher
March 26, 2025, Chirk Castle Gates

no cyclevtrails other than the driveway up to castle but nice tearoom.

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Dave
October 3, 2024, Chirk Tunnel

Interesting to walk through and take a wander on the adjacent aquaduct

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Always a pleasure to see this sign.

2

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Lots of lovely fresh bread available from Smiths Bakery in Oswestry and delicious bloomers hot cross buns. Friendly village shop and one of the oldest post offices

2

0

Great little place. Helped me out with a new pedal when mine broke.

1

0

Frequently Asked Questions

How many road cycling routes are available around Oswestry?

There are over 70 road cycling routes around Oswestry, offering a wide range of options for different skill levels. Approximately half of these, around 36 routes, are classified as easy, making them suitable for relaxed rides.

What kind of landscapes can I expect to see while road cycling near Oswestry?

Road cycling around Oswestry offers diverse landscapes, from quiet country lanes winding through rolling farmland with scenic views of Shropshire and Wales, to routes alongside tranquil canals like the Montgomery Canal. For those seeking more challenge, routes extend into hills and valleys, including the breathtaking scenery of the Tanat Valley and the Eastern Berwyn Hills.

Are there any challenging road cycling routes for experienced riders?

Yes, Oswestry offers routes with significant elevation gain for experienced riders. The region includes challenging climbs in areas like the Tanat Valley and the Eastern Berwyn Hills. An example is the Chirk Tunnel – Chirk Castle Gates loop from Oswestry, a moderate 41.4 km path featuring substantial elevation.

What are some notable attractions or landmarks I can visit along the cycling routes?

Many routes incorporate historical landmarks and natural beauty spots. You can cycle past Whittington Castle or near Chirk Castle. The region also features the scenic Ellesmere Lake, part of Shropshire's Meres, and the Llangollen Canal Towpath. For panoramic views, the Oswestry Old Racecourse is a rewarding climb.

Are there any circular road cycling routes around Oswestry?

Yes, many of the road cycling routes around Oswestry are designed as loops, allowing you to start and finish in the same location. Popular circular options include the Ostwestry to Ellesmere Lake loop via Whittington Castle and the Mereside Lake – Whittington Castle loop from Oswestry.

What is the best time of year to go road cycling in Oswestry?

The best time for road cycling in Oswestry is generally during the spring, summer, and early autumn months when the weather is milder and the days are longer. This allows for comfortable rides through the rolling countryside and along the canals, with the natural features at their most vibrant.

Are there any routes that pass by water features or canals?

Absolutely. The region is known for its beautiful waterways. You can find smooth, traffic-free routes along the Montgomery Canal towpath, which is excellent for relaxed rides and wildlife spotting. Ellesmere Lake, one of Shropshire's Meres, also features in scenic loops, offering a pleasant stop with woodland walks and cafes.

What do other road cyclists enjoy most about cycling in Oswestry?

The road cycling routes in Oswestry are highly rated by the komoot community, with an average score of 4.6 stars from over 5 reviews. Cyclists often praise the varied terrain, from quiet country lanes to more challenging climbs, and the incorporation of historical landmarks and scenic views into the routes.

Can I find routes suitable for a longer distance ride?

Yes, Oswestry offers several routes that cater to longer distances. For example, the Ostwestry to Ellesmere Lake loop via Whittington Castle covers approximately 63.6 km. The area also connects to the broader Shropshire Cycleway, providing options for even more extensive exploration.

Are there any specific viewpoints or scenic spots along the road cycling routes?

Many routes offer stunning vistas. The Oswestry Old Racecourse, an 18th-century horse racing venue, provides panoramic views after a climb. Additionally, routes through the Tanat Valley and Eastern Berwyn Hills are known for their breathtaking scenery. You can also find great views from Llanymynech Hill and Gyrn Moelfre Summit.

Are there any routes that include a waterfall?

For those willing to venture into the more challenging terrain of the Tanat Valley, routes can lead towards natural wonders like Llanrhaeadr Waterfall (Pistyll Rhaeadr), one of the tallest waterfalls in the UK. While not directly on a listed road cycling route in the immediate Oswestry area, it's a significant natural attraction in the wider region.

Are there options for a quick, easy ride?

Yes, there are plenty of easy routes for a quick spin. The region offers options for easy two-hour rides with minimal elevation. The 'Morda Meander' is an 8-mile circular route mostly on quiet roads, with a shorter 4-mile option, perfect for a relaxed outing.

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