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Routes
Running trails & routes
United States
Connecticut
Northwest Hills Planning Region
Winsted

Highland Lake – Holland Beach loop from Winsted

Hard

4.9

(2768)

16,464

runners

Highland Lake – Holland Beach loop from Winsted

01:36

15.3km

150m

Running

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: May 26, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 6 m for 183 m

Customers only

After 15.1 km for 183 m

Customers only

Waypoints

A

Start point

Bus stop

Get Directions

3.66 km

Holland Beach

Beach

5.31 km

Long Point Ridge

Nature Reserve

10.8 km

Highland Lake

Lake

B

15.3 km

End point

Bus stop

Loading

Way Types & Surfaces

Way Types

6.33 km

6.00 km

2.85 km

< 100 m

Surfaces

10.1 km

3.57 km

1.39 km

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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 (290 m)

Lowest point (210 m)

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Weather

Powered by Foreca

Today

Monday 22 June

19°C

12°C

98 %

Additional weather tips

Max wind speed: 15.0 km/h

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Description

If you're seeking a challenging yet incredibly scenic workout, the Highland Lake – Holland Beach loop from Winsted delivers. This difficult 9.5-mile (15.3 km) jogging route, with 487 feet (148 metres) of elevation gain, can be completed in an estimated 1 hour and 36 minutes. It's an ideal choice for runners looking for a longer, rewarding loop with continuous lake views.

What to expect on Highland Lake – Holland Beach loop from Winsted

This route takes you on a journey around the beautiful Highland Lake, primarily following paved roads. While the terrain is mostly flat, you'll encounter a few gradual climbs that add a mild challenge to your jog. The highlight is undoubtedly the crystal-clear waters of Highland Lake itself, reflecting the surrounding trees and sky, especially vibrant during the fall foliage season. You'll pass Holland Beach, one of the public access points, and enjoy a mix of developed shoreline and natural areas, offering a peaceful atmosphere within Connecticut's Northwest Hills. This loop is perfect for those who appreciate a longer road run with consistent, picturesque scenery.

Planning your visit

As this loop utilizes public roads, access is straightforward. Holland Beach is a key public access point, and you can find parking near Holland Beach Highland Lake Winsted CT for runners. The route is popular for local running events, indicating its suitability for joggers. Consider visiting during warmer months for a lively atmosphere or in the fall to experience the stunning vibrant colors of the foliage. Check local public transport options, such as Northwestern Connecticut Transit District bus stops, for accessibility to the area.

Trail details

  • Distance: 9.5 miles (15.3 km)
  • Elevation gain: 487 feet (148 metres)
  • Difficulty: difficult
  • Estimated time: 1 hours and 36 minutes

Nearby routes

Moderate

5.0

56

Hartford Reservoir loop via Red Trail

00:38h

6.12km

50m

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