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Routes
Hiking trails & Routes
United States
Connecticut
Western Connecticut Planning Region

Hemlock Hills and Pine Mountain Trail

Moderate

2.6

(23)

39

hikers

Hemlock Hills and Pine Mountain Trail

03:35

12.7km

260m

Hiking

Embark on the Hemlock Hills and Pine Mountain Trail for a moderate hike spanning 7.9 miles (12.7 km), featuring a total elevation gain of 844 feet (257 metres). You can expect to complete this route in about 3 hours and 35 minutes. As you traverse the path, you will discover…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

1

2.22 km

Lake Windwing

Highlight • Lake

The Lake Windwing area has some nice trails that are fun in the summer and covered with snow in the winter. The lake itself is nice to visit while on …

Tip by

2

2.28 km

Porch Swing

Highlight • Structure

2.96 km

Leibowitz Section

Nature Reserve

4

6.29 km

Bennett's Pond

Highlight • Lake

This pond is part of the headwaters of the Saugatuck River, ultimately providing drinking water to lower Fairfield County. The trail circles the entire pond. We were there in August, …

Tip by

8.36 km

Wooster Mountain

Peak

6

10.5 km

Ives Cabin Chimney Ruin

Highlight • Historical Site

This is all that's left of a cabin built by Charles and Moss Ives in 1903 (Charles Ives was a well-known composer). Here is a picture of what the cabin …

Tip by

7

10.8 km

Great Viewpoint

Highlight • Viewpoint

Very nice place with a wonderful view. Just right for a short break.

Tip by

B

12.7 km

End point

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Way Types & Surfaces

Way Types

12.6 km

146 m

Surfaces

9.90 km

2.72 km

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (280 m)

Lowest point (160 m)

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Weather

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Today

Tuesday 26 May

27°C

12°C

0 %

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Max wind speed: 12.0 km/h

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Frequently Asked Questions

How long does it take to hike the Hemlock Hills and Pine Mountain Trail?

The full route, covering approximately 12.7 kilometers (about 7.9 miles), typically takes around 3 hours and 35 minutes to complete. This duration is for hiking and does not include stops for breaks or enjoying the scenery.

What is the terrain like on this trail?

The trail offers a diverse hiking experience. You'll encounter rocky and wooded singletrack, granite outcrops, and areas with swamps. The northern part features vast hemlock stands, while other sections have unique rock formations, some striated from glacial action. Expect varied landscapes, including some steep sections.

Are there any notable landmarks or viewpoints along the route?

Yes, the trail offers several points of interest. You'll pass by Lake Windwing and Bennett's Pond. A significant historical feature is the Ives Cabin Chimney Ruin, believed to be from composer Charles Ives's cabin. There's also a Great Viewpoint offering views of hills to the south, Ridgebury School, and Barlow Mountain.

Is the Hemlock Hills and Pine Mountain Trail suitable for beginners or is it challenging?

The trail is generally rated as moderate. While some sections are relatively easy, there are three steep climbs, and the Yellow Trail - Pine Mountain portion is considered the most strenuous, involving an uphill climb along a rocky slope. Hikers should be prepared for varied difficulty depending on the specific loop chosen.

What is the best time of year to hike this trail?

Spring and fall are often ideal for hiking this trail, offering pleasant temperatures and beautiful foliage. In spring, you can see an unusual abundance of marsh marigolds in swampy areas. The diverse flora, including mountain laurel, also makes for a scenic experience. Winter hiking is possible, but conditions can be challenging with snow and ice.

Is the trail dog-friendly?

Yes, dogs are generally welcome on the Hemlock Hills and Pine Mountain Trail. However, it's always best to keep your dog on a leash to protect wildlife and ensure a pleasant experience for all hikers. Please remember to pack out any waste.

Do I need a permit or is there an entrance fee for hiking here?

The Hemlock Hills and Pine Mountain Trail is located within Bennett's Pond State Park. Generally, there are no entrance fees or permits required for day-use hiking in Connecticut State Parks. However, always check the official Connecticut State Parks website for the most current regulations before your visit.

Where can I park to access the Hemlock Hills and Pine Mountain Trail?

Specific parking information for this trail is not detailed in the provided data, but access points are typically found near the Pine Mountain entrance or other designated trailheads within Bennett's Pond State Park. It's advisable to check local park maps or online resources for precise parking locations before heading out.

Does the trail intersect other well-known paths?

Yes, the route incorporates sections of several other trails. You will hike along parts of the Ives Trail Greenway, the White Trail, the Blue Trail, the Red Trail, and the Ives Trail, offering a connected network of paths through the area.

What kind of plants and wildlife might I see on the trail?

The trail boasts rich flora, including vast hemlock stands, mountain laurel (Connecticut's state flower), striped maple, witch hazel, and pignut hickory. In swampy areas, you might spot an unusual abundance of marsh marigolds. The diverse habitats also support various local wildlife, though specific sightings can vary.

Are there any specific challenges or unique features to be aware of?

Beyond the steep sections, hikers should be aware of multiple stream crossings near the Pine Mountain entrance. The trail also passes through areas with marble deposits, which influence the unique plant life found here, and offers interesting geological features like granite plateaus and glacial rock formations.

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