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Routes
Running Trails
United States
New Hampshire
Cheshire County

Winchester

The best running trails around Winchester

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runners

3

runs

Jogging around Winchester offers a varied landscape for runners, encompassing both urban and natural environments. The region features expansive parklands with established trail networks, serene river paths, and forested areas. Runners can find routes traversing chalk downland, ridgelines, and wetlands, alongside trails that connect urban areas with natural beauty. The terrain ranges from flat, gentle paths along waterways to more challenging routes with significant elevation gain through hills and woodlands.

Best jogging routes around Winchester

  • The most popular jogging route…

Last updated: April 27, 2026

1

runners

#1.

Kilburn Loop

4.85km

00:32

50m

50m

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

10.3km

01:21

270m

270m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Popular around Winchester

Hiking around Winchester

Cycling around Winchester

Road Cycling Routes around Winchester

Tips from the Community

mtm05005
November 8, 2023, Kilburn Trailhead

Trailhead with parking that lets you choose whether to take the paths that bring you east to Pisgah State Forest or west to Daniels Mountain. In the high season it can get busy, so make sure to get there early to get a parking spot.

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mtm05005
October 17, 2023, Hubbard Hill Trail

The Hubbard Hill Trail is a great, wooded path. It leads up to the peak of Hubbard Hill, so there is a sustained incline. Due to the elevation gain, the trail is considered to be moderate difficulty.

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At the base of Pisgah ridge, you can look out over scenic Pisgah Reservoir, the western lobe of which is also known as Round Pond. The trail east of here crosses Pisgah Brook, which connects the chain of reservoirs along the east side of the ridge.

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mtm05005
October 17, 2023, Lily Pond Trail

Nice, easy trail that runs next to a beautiful pond. The path is normally not too busy, so there is a good chance you might get the whole trail to yourself.

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Zachary
October 17, 2023, Mount Pisgah

Mount Pisgah is the highest point in Pisgah state park at around 1300 feet. From here you get a great view of the forest, the reservoirs, and over into Vermont.

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Zachary
October 17, 2023, Kilburn Pond

The pond is great for swimming and the edge is lined with large stones that are perfect for scrambling, picnicking, and enjoying the water.

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mtm05005
October 17, 2023, Kilburn Trailhead

Trailhead with parking that lets you choose whether to take the paths that bring you east to Pisgah State Forest or west to Daniels Mountain. In the high season it can get busy, so make sure to get there early to get a parking spot.

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The Fort Hill Recreational Trail is a 9-mile long multiuse trail that is built along the old Boston and Maine Railroad. The surface is crushed stone and gravel and is a great place for a quiet run.

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Frequently Asked Questions

What types of terrain can I expect on running routes around Winchester?

Winchester offers a diverse landscape for runners. You'll find routes traversing chalk downland, ridgelines, and mature forests, particularly within the South Downs National Park in the UK. There are also tranquil river paths along the River Itchen, expansive parklands, and forested hills. The terrain varies from flat, gentle paths to more challenging routes with significant elevation gain.

Are there any easy or beginner-friendly jogging routes in the Winchester area?

Yes, for those seeking a gentler run, the Kilburn Loop is an excellent choice. This 3.0-mile (4.8 km) trail offers a moderate experience through local green spaces with minimal elevation gain, making it suitable for beginners or a relaxed run.

Which running trails offer scenic views or interesting natural features?

Many routes provide beautiful scenery. In Winchester, UK, trails around St Catherine's Hill offer panoramic views of the city and the Itchen Valley. The River Itchen and its water meadows provide peaceful, flat routes. For a unique experience, the Mount Pisgah via Parker Trail leads through forested areas with notable elevation gain, offering a different kind of natural beauty.

Are there any longer distance running trails available?

Absolutely. For a longer run, consider the Hubbard Hill Loop Trail, which spans 6.4 miles (10.3 km) and features significant elevation changes, making it a good option for those looking to challenge themselves over a greater distance. Another option is the Fort Hill Recreational Rail Trail, a 6.0-mile (9.7 km) path that follows a former railway line, providing a relatively flat surface suitable for longer, steady runs.

Can I find circular running routes around Winchester?

Yes, several routes are designed as loops. The Kilburn Loop is a popular circular route through green spaces. Another excellent option is the Chestnut Hill, Reservoir, and North Ponds Trail Loop, which offers a varied experience around natural water features.

What kind of landmarks or points of interest can I see while running in Winchester?

While running around Winchester, you can encounter various points of interest. For example, the Fort Hill Recreational Trail itself is a notable feature. You might also pass through areas like Mount Grace State Forest or along the Hubbard Hill Trail and Lily Pond Trail, which offer natural beauty. In Winchester, UK, the historic Hockley Viaduct and the tranquil The Weirs walkway along the River Itchen are also points of interest.

Are there any challenging running trails with significant elevation gain?

For runners looking for a challenge, the Hubbard Hill Loop Trail features an elevation gain of approximately 270 meters over its 6.4-mile distance. Similarly, the Mount Pisgah via Parker Trail includes about 236 meters of ascent, providing a good workout through forested areas.

What do other runners enjoy most about jogging in Winchester?

The komoot community appreciates the varied landscape of Winchester. Runners often praise the mix of urban and natural environments, from serene river paths to challenging forested hills. The availability of routes for different ability levels and the scenic beauty of areas like the South Downs National Park and the River Itchen are frequently highlighted.

Are there any running routes that are particularly good for families or with children?

While specific family-friendly routes are not detailed in the guide, generally, flatter and shorter trails are best for families. The River Itchen paths in Winchester, UK, are known for being peaceful and flat, which could be suitable for a gentler run with children. The Kilburn Loop, being an easy route through green spaces, could also be a good option for families.

Are there options for running trails accessible by public transport in Winchester?

The guide focuses on the routes themselves, but in Winchester, UK, many trails, especially those along the River Itchen or near St Catherine's Hill, are often accessible from the city center, which is well-served by public transport. For specific public transport links to trailheads, it's advisable to check local transport schedules for the starting points of your chosen route.

What is the best time of year for jogging in Winchester?

Winchester offers enjoyable running conditions throughout much of the year. Spring and autumn provide pleasant temperatures and beautiful scenery, especially with the changing foliage in forested areas. Summer is also popular, though it's best to run in the mornings or evenings to avoid the midday heat. Winter runs can be invigorating, particularly on well-maintained paths, but be mindful of potentially muddy or icy conditions on unpaved trails.

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