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United States
Missouri
St. Louis County

Winchester

The best walks and hikes around Winchester

4.7

(25)

464

hikers

37

hikes

Hiking around Winchester offers a variety of trails through woodlands and along riverbanks, characterized by rolling hills and mostly gentle elevation changes. The region features well-maintained paths through state parks and local nature areas. These routes provide options for both shorter and longer hikes across varied terrain. The landscape includes open paths with gradual climbs and forested sections.

Best hiking trails around Winchester

  • The most popular hiking route is Riverscene Trail loop, a 3.4 miles (5.5 km) trail that…

Last updated: May 12, 2026

5.0

(2)

7

hikers

#1.

Riverscene Trail

2.90km

00:44

0m

0m

Hike the easy 1.8-mile Riverscene Trail in Castlewood State Park, enjoying river views and historical remnants.

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Easy

3

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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1.98km

00:32

30m

30m

Enjoy an easy 1.2-mile hike on the Bluebird Park Trail in Ellisville, Missouri, featuring lush greenery and diverse natural beauty.

Easy

4.3

(6)

68

hikers

5.51km

01:27

50m

50m

Hike the Riverscene Trail loop in Castlewood State Park, an easy 3.4-mile route offering bluff views and a riverside path along the Meramec

Easy

5.0

(1)

43

hikers

6.48km

01:43

60m

60m

Hike the easy 4.0-mile Hawk Ridge Trail loop in Queeny Park, St. Louis, Missouri, featuring woodlands, open fields, and historic landmarks.

Easy
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Popular around Winchester

Cycling around Winchester

MTB Trails around Winchester

Running Trails around Winchester

Road Cycling Routes around Winchester

Tips from the Community

Grace Mulligan
December 29, 2023, Queeny Park

Queeny Park has a network of paved footpaths that are perfect for running. Hawk Ridge Trail is the longest circling the entire park, and then Owl Creek and Goose Trail are slightly shorter and perfect if you're looking for a shorter run. The park features a number of interesting buildings, native trees, prairies and picnic areas.

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Grace Mulligan
December 27, 2023, Queeny Park

This is a sprawling park featuring beautiful nature, a collection of fascinating buildings, picnic areas and a network of walking trails. It's one of the largest parks in St Louis County and perfect location for a stroll in nature.

1

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Matthew
September 1, 2023, Riverscene Trail

The Riverscene Trail is the most popular trail in Castlewood State Park. The trail passes through a forest scene, a wide open are next to a beach area, and along the banks of a shaded river. The variety of scenery with pretty smooth terrain makes this loop trail a perfect choice for a lot of different occasions.

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Frequently Asked Questions

Are there many circular walks available around Winchester?

Yes, the area is excellent for circular walks. Many trails are designed as loops, allowing you to start and end at the same point without retracing your steps. For a shorter loop, the Hiking loop from Castlewood State Park is a great option that takes you through pleasant woodland scenery.

Can I bring my dog on the hiking trails near Winchester?

Most trails in the Winchester area are dog-friendly, but it's always best to keep your dog under control, especially near wildlife or livestock. The open spaces of the South Downs and riverside paths are popular with dog walkers. Just be mindful of local signage regarding leads.

Are there any easy, family-friendly walks in the area?

Absolutely. Winchester offers many gentle walks suitable for the whole family. The paths through Winnall Moors Nature Reserve are flat, well-maintained, and offer great opportunities for spotting wildlife. Another excellent choice is the Riverscene Trail loop from Twin Oaks, which is a relatively short and easy walk along the river.

Where can I find the best views while hiking near Winchester?

For some of the most rewarding panoramic views, head to St. Catherine's Hill. After a steep climb, you'll be treated to stunning vistas over the city and the Itchen Valley. Old Winchester Hill is another local favorite, offering beautiful countryside views from its Iron Age hillfort.

How can I get to the hiking trails using public transport?

Winchester's central train station provides excellent access to the city. From there, many trails are within walking distance, including the start of the South Downs Way, the Itchen Way, and walks to St. Catherine's Hill. Local bus services can also take you closer to trailheads further afield, such as those around the surrounding villages.

What are some popular places for hiking in Winchester?

Hikers in Winchester have several highly-regarded spots to explore. St. Catherine's Hill is a top choice for its dramatic views and historic features. For a peaceful walk with abundant wildlife, the Winnall Moors Nature Reserve is a protected area right near the city. Shawford Down also serves as a great starting point for various walks through woodland and open grassland.

Are there any challenging hikes available?

While the region is known for its gentle rolling hills, you can find more challenging options. The Hiking loop from Twin Oaks offers some of the area's more significant elevation gain. For a long-distance challenge, you can tackle a section of the South Downs Way, which begins in Winchester and features sustained climbs and descents.

What is the terrain like on the trails around Winchester?

The landscape is primarily defined by the rolling chalk hills of the South Downs and the flat water meadows along the River Itchen. You can expect a mix of woodland paths with tree roots, open grassland trails, and well-maintained riverside footpaths. Most routes feature gentle to moderate elevation changes.

Where can I find a good walk along the River Itchen?

The Itchen Way is a long-distance path that follows the river, and several shorter sections are easily accessible from Winchester. A popular route is Keats' Walk, a gentle and scenic trail that takes you from the city centre along the river through the famous water meadows.

What do other hikers think of the trails in Winchester?

The trails around Winchester are highly rated by the komoot community, with an average score of 4.9 stars. Hikers often praise the beautiful scenery, the variety of walks available, and the well-maintained paths that make exploring the region's woodlands and rolling hills a pleasure.

Is parking available at the trailheads?

Parking varies by location. Some popular spots like Old Winchester Hill and Shawford Down have dedicated car parks, though they can fill up on weekends. For trails starting in the city, it's often easier to use one of the city's Park & Ride services or public car parks and walk to the trailhead.

Are there any forested or woodland hikes?

Yes, many trails lead through beautiful woodlands. The Hawk Ridge Trail loop is a great example, offering a peaceful walk almost entirely through forested areas. Farley Mount Country Park to the west of the city also has extensive woodland to explore.

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