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Routes
Running Trails
United States
Connecticut
Northwest Hills Planning Region

Chimney Point

The best running trails around Chimney Point

17

runners

2

runs

Jogging around Chimney Point offers a variety of routes through diverse landscapes. The region features moderate elevation changes, with trails winding through areas that combine open spaces and some wooded sections. Runners can expect paths that provide both distance and some gentle climbs, suitable for various fitness levels. The terrain primarily consists of established paths and natural surfaces, making it ideal for running.

Best jogging routes around Chimney Point

  • The most popular jogging route is Zalesskys Pond – Parkhurst Pond loop from New Milford, a 8.0 miles (12.8 km) trail that takes 1 hour 22 minutes to complete. This route offers a substantial distance with moderate elevation gain.
  • Another top favourite among local runners is Running loop from New Milford, a moderate 3.1 miles (5.0 km) path. This trail provides a shorter option with less elevation, suitable for a quicker run.
  • Local runners also love the Whalen Pond loop from Brookfield, a 4.2 miles (6.8 km) trail leading through varied terrain, often completed in about 42 minutes.
  • Jogging around Chimney Point is defined by moderate elevation changes, a mix of open and wooded areas, and established paths. The network offers options for different ability levels, from shorter loops to longer distance running trails Chimney Point.
  • The guide includes highly-rated routes that showcase the best of the region's landscape. More than 10 runners have used komoot to explore Chimney Point's varied terrain.

Last updated: July 1, 2026

6

runners

#1.

Zalesskys Pond – Parkhurst Pond loop from New Milford

12.8km

01:22

190m

190m

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

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Moderate

4

runners

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

Moderate
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2

runners

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

Moderate

3

runners

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

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

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Frequently Asked Questions

How many running routes are available in Chimney Point?

Komoot features a selection of running routes around Chimney Point, offering a variety of options for different preferences. Currently, there are several curated routes available in this guide.

Are there any longer running trails for endurance training in Chimney Point?

Yes, for those looking for a longer run, the Zalesskys Pond – Parkhurst Pond loop from New Milford offers a substantial 8.0 miles (12.8 km) trail. It features moderate elevation changes, making it suitable for a good endurance workout.

What kind of terrain can I expect on the running routes in Chimney Point?

The running routes in Chimney Point generally feature moderate elevation changes, with paths winding through a mix of open spaces and some wooded sections. You'll primarily encounter established paths and natural surfaces, providing a varied running experience.

Are the running trails in Chimney Point suitable for beginners or families?

While all routes in this guide are rated as moderate, shorter options like the Running loop from New Milford (3.1 miles / 5.0 km) or the Ball Pond loop from Taylor Corners (3.2 miles / 5.1 km) are excellent choices for beginners or families looking for a less strenuous run. They offer less elevation and a quicker completion time.

Can I find circular running routes in Chimney Point?

Many of the running routes in Chimney Point are designed as loops, allowing you to start and finish at the same point. Examples include the Whalen Pond loop from Brookfield and the Running loop from Brookfield, providing convenient options for your run.

When is the best time of year to go running in Chimney Point?

Spring and fall generally offer the most pleasant running conditions in Chimney Point, with mild temperatures and beautiful scenery. Summer can be warm, so early morning or late afternoon runs are advisable. Winter running is possible, but be prepared for colder temperatures and potential snow or ice on trails.

Are the running routes in Chimney Point dog-friendly?

Most outdoor trails in the Chimney Point area are generally dog-friendly, especially if your dog is on a leash. However, it's always recommended to check specific local regulations or signage at trailheads for any restrictions before heading out with your furry companion.

What are some scenic highlights I might encounter on a run in Chimney Point?

The routes often feature natural beauty, including ponds and wooded areas. For instance, the Zalesskys Pond – Parkhurst Pond loop takes you past two distinct ponds, offering tranquil water views and a refreshing environment for your run.

Is parking generally available near the running trailheads in Chimney Point?

Yes, for many of the routes originating from towns like New Milford or Brookfield, you can typically find parking options near the trailheads or in designated public areas within these communities. It's advisable to check local maps or specific route details for precise parking information.

Are there any challenging running options for experienced runners in Chimney Point?

While all routes in this guide are rated moderate, the longer distances and cumulative elevation gain on trails like the Zalesskys Pond – Parkhurst Pond loop can provide a good challenge for experienced runners. The varied terrain and moderate climbs will test your stamina.

What do other runners enjoy most about the trails in Chimney Point?

Runners often appreciate the diverse landscape of Chimney Point, which combines open spaces with wooded sections. The established paths and moderate elevation changes are frequently praised for offering a balanced and enjoyable running experience suitable for various fitness levels.

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