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United Kingdom
England
South East England
Buckinghamshire
Aylesbury Vale

Winslow

The best walks and hikes around Winslow

4.4

(133)

1,070

hikers

130

hikes

Hiking around Winslow explores the rural landscape of Buckinghamshire. The region is characterized by gentle terrain within the Aylesbury Vale, featuring a patchwork of open fields, farmland, and meadows. Routes often follow meandering streams like the Claydon Brook and pass through small pockets of woodland.

Best hiking trails around Winslow

  • The most popular hiking route is The Pilgrim Pub, North Marston – North Marston Village loop from Granborough, a 10.5 mile (16.9 km) trail that takes about 4 hours 30 minutes to complete. This moderate route crosses open fields and follows quiet country paths.
  • Another top favourite among local hiking enthusiasts is Runt's Wood – Romer Wood loop from East Claydon, a moderate 6.7 mile (10.8 km) path. The trail leads through sections of woodland and across the area's typical flat farmland.
  • Local hiking enthusiasts also love the St Laurence Church, Winslow loop from Winslow, a 4.9 mile (7.8 km) trail leading through the countryside surrounding the town, often completed in about 2 hours.
  • Hiking around Winslow is defined by pastoral fields, quiet woodlands, and paths along streams. The network of over 140 routes offers options for different ability levels, with the majority being easy or moderate.
  • The routes in Winslow are highly rated by the komoot community with an average score of 4.5 stars from over 120 reviews. More than 1,100 hikers have used komoot to explore Winslow's varied terrain.

Last updated: May 5, 2026

3.8

(6)

20

hikers

#1.

The Farm Deli, Winslow – Crumbs Winslow Café loop from Winslow

9.26km

02:24

50m

50m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Popular around Winslow

Midshires Way — An epic hike through England's rural heart

Road Cycling Routes around Winslow

Running Trails around Winslow

MTB Trails around Winslow

Cycling around Winslow

Other adventures around Winslow

Midshires Way — An epic hike through England's rural heart

Hiking Collection by

Alex Foxfield

Tips from the Community

foxy44
October 25, 2025, George & Dragon Coffee Shop & Tea Room, Quainton

Open every day of the week except Monday, popular with locals and cyclists alike. Great coffee, lovely selection of cakes, bacon sandwiches, plus many other options. Inside and outside seating.

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There is a water tap in the courtyard to fill bidons.

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late was £4

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Very flat walk nice and easy

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Lovely National Trust House, with memorabilia of Florence Nightingale, a Gamelan Orchestra and exquisite carving and mouldings.

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When I called approx 2mths ago the pub and cafe were closed with board posted. It is possible some one else may be found to to reopen it....

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From Ledburn to Marsh Gibbon and back (50 miles) with this cafe just over half away around. A welcome stop just before the two long hills into Whitchurch and Cubblington. A great place to stop and refuel! Good coffee, good food, friendly staff, pretty village and just as important, friendly locals!

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A nice spot to rest the legs or dodge a shower. As well as admiring the restored thatch and ancient tree. Walk a few yards for some expansive countryside views

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Frequently Asked Questions

What is the terrain like for hiking around Winslow?

The hiking around Winslow is characterized by the gentle, rolling landscape of the Aylesbury Vale in Buckinghamshire. You can expect routes that cross a patchwork of open fields, farmland, and meadows, often following meandering streams like the Claydon Brook and passing through small pockets of woodland.

Are there many difficult hikes in the Winslow area?

No, the region is best known for its accessible trails. Out of more than 140 routes, the vast majority are rated as easy or moderate, making it an ideal destination for relaxed walks and family outings. There are no designated difficult or expert-level hikes.

Are the hiking trails near Winslow suitable for families with children?

Yes, Winslow is very family-friendly. The gentle terrain and abundance of easy routes make it a great choice for hikers of all ages. For a shorter, manageable walk, consider the Addington Parish Church loop from Addington, which is just over 5 km and explores the quiet countryside.

Can I take my dog on the trails around Winslow?

Most countryside paths and public footpaths around Winslow are suitable for dogs. However, you will likely cross fields with livestock, so it's essential to keep your dog on a lead in these areas. Always follow the Countryside Code and respect local signage.

What do other hikers think of the trails in Winslow?

The trails are highly regarded by the komoot community, with reviewers often praising the peaceful rural scenery and quiet country paths. The area has an average rating of over 4 stars, based on more than 120 reviews from fellow hikers.

Are there any circular walks that start and end in the same place?

Yes, many of the best routes are circular. A great option that starts near the town is the St Laurence Church, Winslow loop from Winslow. This trail allows you to explore the surrounding fields and return to your starting point without needing to retrace your steps.

What should I pack for a day hike in Winslow?

For a day hike, you should wear sturdy walking shoes or boots, as paths can be muddy, especially after rain. It's wise to bring waterproof clothing, even on a clear day. Also pack water, snacks, and a fully charged phone with the komoot app for navigation.

How can I get to the trailheads using public transport?

Winslow has a railway station with connections to nearby towns, making it possible to access some trails without a car. Several routes start directly from the town or nearby villages which may be served by local bus routes. Check local bus and train schedules to plan your journey.

Are there any good options for a shorter, easy hike?

Absolutely. The area has nearly 100 easy-rated trails. A popular choice for a straightforward and pleasant walk is the Hiking loop from Swanbourne. At around 6 km, it's a great way to experience the local landscape without committing to a long day of hiking.

What is the best time of year to hike in Winslow?

Hiking is possible year-round, but spring and summer are particularly beautiful when the fields are green and the weather is mild. Autumn offers lovely colours in the woodlands. Winter walks can be rewarding on crisp, clear days, but be prepared for muddy and wet conditions underfoot.

Are there any hikes that go through woodlands?

Yes, while the area is dominated by open farmland, some routes feature pleasant woodland sections. For a trail that combines woods and fields, try the Runt's Wood – Romer Wood loop from East Claydon, which takes you through two local woods.

Where can I find a longer, more challenging hike?

For those seeking a longer day out, The Pilgrim Pub, North Marston – North Marston Village loop from Granborough is a great choice. This moderate route is nearly 17 km and takes you across open fields and along quiet country paths, offering a more substantial challenge.

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