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Routes
Running Trails
United States
Connecticut
Western Connecticut Planning Region

Lakeside Woods

The best running trails around Lakeside Woods

31

runners

8

runs

Jogging around Lakeside Woods offers access to diverse landscapes, characterized by extensive trail systems and varied terrain. The region features wooded areas, rugged hill country, and stretches of lakeshore, providing a range of environments for running. These natural settings include oak-hickory forests and areas with unique cedar-like trees. The network of routes allows for exploration of both challenging and more level paths.

Best jogging routes around Lakeside Woods

  • The most popular jogging route is Running loop from Village of Pawling

Last updated: August 21, 2026

7

runners

#1.

Running loop from Pawling

6.40km

00:40

50m

50m

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

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Moderate

6

runners

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

3

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
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Frequently Asked Questions

How many running routes are available in Lakeside Woods?

Lakeside Woods offers a selection of 8 dedicated jogging routes. These routes cater to various preferences, with a strong emphasis on moderate challenges, ensuring a rewarding experience for most runners.

What kind of terrain can I expect when jogging in Lakeside Woods?

You can expect diverse terrain, ranging from extensive wooded trails and rugged hill country to scenic lakeshore paths. Some areas feature significant elevation changes, such as a set of 315 man-made stone steps, while others offer more relatively level loops like the Ridgetop Trail mentioned in some parts of the region. The landscape includes oak-hickory forests and unique cedar-like trees.

Are there options for different fitness levels?

Yes, while most routes are classified as moderate, there is one more challenging option for experienced runners. The moderate trails offer varied distances and elevations, ensuring there's something suitable whether you're looking for a steady jog or a more vigorous workout.

Are there any scenic viewpoints or natural features to discover while running?

Absolutely. Many trails offer stunning views, particularly of Lake Taneycomo. You might also encounter unique natural features like the Grotto, which forms a spectacular waterfall during rainy periods, and areas with blooming Eastern Redbuds and Flowering Dogwoods in spring. For specific highlights, consider exploring areas near Squantz Pond State Park or the River Trail.

Can I see any historical or unique landmarks on the trails?

Yes, some areas of Lakeside Woods feature interesting historical and unique landmarks. You might discover an old soldier's cave, impressive hand-built stone walls, and a large wooden log archway marking trail entrances. These elements add a touch of historical charm to the natural setting.

Are there any circular running routes in Lakeside Woods?

Yes, many of the running routes in Lakeside Woods are designed as loops, offering a convenient way to start and finish your run at the same point. Examples include the Running loop from Village of Pawling and the Zalesskys Pond – Parkhurst Pond loop from New Milford, which are popular choices among local runners.

Are the running trails suitable for families?

While the guide primarily features moderate routes, some areas within Lakeside Woods, such as those with picnic areas and nature playgrounds, are very family-friendly. For a more relaxed experience, look for trails described as relatively level, like the Ridgetop Trail, which can be suitable for a family jog or stroll.

What is the average distance and elevation gain for runs in this region?

The running routes in Lakeside Woods vary in length and elevation. For instance, the Running loop from Village of Pawling is about 4 miles (6.4 km) with around 46 meters of elevation gain, while the Zalesskys Pond – Parkhurst Pond loop from Washington covers about 8.5 miles (13.6 km) with nearly 200 meters of elevation gain.

What do other runners enjoy most about jogging in Lakeside Woods?

Runners frequently praise the diverse landscapes, from serene wooded areas to rugged hill country and picturesque lakeshore paths. The variety of terrain and the opportunity to discover natural features like waterfalls and historical stone walls make for an engaging and rewarding running experience.

Are there any specific trails that go around lakes or ponds?

Yes, several routes incorporate beautiful lakeside scenery. For example, the Spring Lake loop from Sherman leads through natural woodlands and directly around Spring Lake. Another popular option is the Zalesskys Pond – Parkhurst Pond loop from New Milford, which features sections near ponds.

Is there a map available for the trails in Lakeside Woods?

While komoot provides detailed maps for each route, for a broader overview of some areas within Lakeside Woods, you might find external resources helpful. For example, a map of the Lakeside Forest Wilderness Area trails can be found at bransontourismcenter.com.

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