
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.
Last updated: July 1, 2026
6
runners
12.8km
01:22
190m
190m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
runners
5.04km
00:32
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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2
runners
6.82km
00:43
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
runners
9.62km
01:00
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
runners
5.17km
00:32
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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