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Routes
Running Trails
United States
Connecticut
Western Connecticut Planning Region

Topstone

Photo: Liv

The best running trails around Topstone

5.0

(2)

122

runners

28

runs

Jogging routes around Topstone offer diverse landscapes, including a scenic pond, accessible trails, and elevated viewpoints. The region features Topstone Mountain, providing varying terrain and rewarding views. Trails wind through 280 acres, encompassing natural features and historical significance. This combination creates an inviting environment for outdoor activities like jogging.

Best jogging routes around Topstone

  • The most popular jogging route is Silver Springs Swamp Dam – Prospect Hill loop from Weir Farm, a 13.3 miles (21.5 km) trail that takes…

Last updated: May 16, 2026

19

runners

#1.

Silver Springs Swamp Dam – Prospect Hill loop from Weir Farm

21.5km

02:15

190m

190m

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

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

Moderate
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10

runners

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

Easy

7

runners

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

Moderate

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Tips from the Community

Jamie S.
February 19, 2024, Silver Springs Swamp Dam

At this spot Silver Springs Swamp flows over a small dam into a small stream. This is a very pretty place to ride past as you explore the area.

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Frequently Asked Questions

How many running routes are available in the Topstone area?

There are over 30 dedicated running routes around Topstone, catering to various skill levels. You'll find options ranging from easy, flat paths to more challenging trails with significant elevation changes.

What kind of terrain can I expect on the jogging trails in Topstone?

The terrain in Topstone is quite varied, offering a mix of landscapes. You can expect trails that wind around the scenic 25-acre pond, as well as paths that ascend Topstone Mountain, providing elevated viewpoints. Some routes feature easy grades, while others present more challenging ascents and descents.

Are there any family-friendly running routes in Topstone?

Yes, Topstone offers several routes suitable for families. For an easier option, consider the Prospect Hill loop from Ridgefield, which is about 5 kilometers long and features varied terrain. The Pond Trail, just under a mile, also offers frequent views of the water and is generally an easy path.

What are some notable natural features or viewpoints I can see while running in Topstone?

Topstone Park is rich in natural beauty. A central feature is its beautiful 25-acre pond, which many trails run alongside. For breathtaking views, the Stuart Chase Long View Trail ascends Topstone Mountain, offering expansive vistas of the pond and, in all seasons, a 'very long view' towards Long Island Sound, considered one of the best overlooks in Redding. You can also find highlights like Parks Pond and Picnic Site and various viewpoints like the View of Saugatuck Reservoir.

Are there any historical landmarks along the running routes?

Topstone Park itself holds historical significance, as it was formerly part of the estate of renowned photographer Edward Steichen. While jogging, you might also encounter nearby historical sites such as Weir Farm National Historical Park, which offers a glimpse into the region's past.

What is the best time of year to go jogging in Topstone?

Topstone offers a great running experience year-round. The 'long view' from Topstone Mountain is enjoyable in all seasons. During summer, the park's pond features a guarded swimming area, making it a refreshing stop after a run. Spring and autumn offer pleasant temperatures and vibrant foliage, ideal for exploring the 280 acres of trails.

Are there any circular running routes in the Topstone area?

Yes, many of the routes in Topstone are designed as loops, allowing you to start and finish at the same point. Examples include the The Corner loop from Redding, a moderate 5.2 km route, and the more challenging Umpawaug Pond – Hawley Pond loop from Redding, which spans nearly 19 kilometers.

What do other runners say about the trails in Topstone?

The running routes in Topstone are highly regarded by the komoot community, boasting an average rating of 5.0 stars. Over 135 runners have explored the varied terrain, often praising the scenic pond views, accessible trails, and elevated viewpoints from Topstone Mountain.

Are there options for longer, more challenging runs in Topstone?

Absolutely. For those seeking a more demanding run, the area provides several difficult routes. The Umpawaug Pond – Hawley Pond loop from Redding is a challenging 18.8 km route with significant elevation gain, perfect for experienced runners.

Can I find places to relax or picnic near the running trails?

Yes, Topstone Park is well-suited for relaxation and picnicking. The park features a sand beach and picnic areas, particularly around the 25-acre pond. You can also find the Parks Pond and Picnic Site, offering a pleasant spot to unwind after your run.

Is there public transport available to reach the Topstone running trails?

While specific public transport routes directly to Topstone Park may be limited, the park is located in Redding, Connecticut. For detailed information on reaching the park via public transport, it's best to consult local transit authority websites or services like CTvisit.com's listing for Topstone Park for directions and accessibility.

Are there any opportunities for wild swimming near the running routes?

Topstone Park's 25-acre pond is a central feature, offering a sand beach and a guarded swimming area during the summer months. This provides a great opportunity for a refreshing dip after a run, though it's not strictly 'wild swimming' due to the managed facilities. For other natural water bodies, you might find highlights like Godfrey Pond and Bennett's Pond in the wider area.

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