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Routes
Road cycling routes
United States
Connecticut
South Central Connecticut Planning Region

Lake Waramaug State Park – Lake Waramaug loop from Southbury

Routes
Road cycling routes
United States
Connecticut
South Central Connecticut Planning Region

Lake Waramaug State Park – Lake Waramaug loop from Southbury

Moderate

2.7

(23)

51

riders

Lake Waramaug State Park – Lake Waramaug loop from Southbury

04:28

95.3km

900m

Road cycling

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is right next to a parking lot.

Last updated: May 6, 2026

Tips

The surface along some of this route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 745 m for 809 m

After 62.7 km for 2.92 km

Waypoints

A

Start point

Parking

Get Directions

1

832 m

Larkin State Park Trail

Highlight • Trail

It's an awesome and easy trail. It's never too hard, pretty even terrain all the way there and back. Very few gradual climbs.

Tip by

2

897 m

Larkin State Park Trail

Highlight (Segment) • Trail

The trail stretches for 10.3 miles, winding through the woods and around lakes and low hills in four towns: Southbury, Oxford, Middlebury, and Naugatuck. It follows the former New York …

Tip by

3

7.68 km

Bates Rocks

Highlight • Natural Monument

Part of a quaint lumpy wooded ridge-line that is formed by East Hill in the SW and Bates Rocks in the NE.

Tip by

4

11.8 km

Hesseky Meadow Pond

Highlight • Lake

A nice pond surrounded by lush green surroundings. It makes for a very nice and scenic ride, allowing you to be at peace as you cruise.

Tip by

5

47.1 km

Lake Waramaug State Park

Highlight • Lake

This small lake-side park comes equipped with picnic benches and plenty of trees to provide shade on a summers day. A great spot to take a break.

Tip by

6

52.3 km

Lake Waramaug

Highlight • Lake

7

87.2 km

Radey Pond

Highlight • Lake

Radey Pond is a body of water that flows down from the Janie Pierce Park dam via Hesseky Brook. This section of road right along the borders of the pond …

Tip by

B

95.3 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

77.2 km

14.2 km

3.19 km

828 m

< 100 m

Surfaces

88.9 km

2.73 km

2.10 km

1.61 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 (310 m)

Lowest point (60 m)

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Weather

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Thursday 16 July

27°C

19°C

-- %

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Description

If you're looking for a substantial road cycling challenge that rewards you with classic New England scenery, the Lake Waramaug State Park – Lake Waramaug loop from Southbury is definitely worth your time. This moderate 59.2-mile (95.3 km) route packs in 2942 feet (897 metres) of climbing, taking around 4 hours and 28 minutes to complete. It's perfect for experienced cyclists ready for a long day in the saddle, combining a scenic lake loop with a significant journey to get there.

What to expect on Lake Waramaug State Park – Lake Waramaug loop from Southbury

The journey begins in Southbury, leading you through the rolling, hilly terrain typical of the Litchfield Hills. As you approach Lake Waramaug, the landscape opens up to reveal picturesque views of the lake, dotted with charming cottages and docks. You'll cycle past fragrant lilacs and lilies, and further on, the scenery shifts to pastoral meadows with grazing cows. The roads around the lake, including Lake Waramaug Road and Shore Road, are winding and can be narrow, requiring confident cycling. Don't miss a potential stop at Hopkins Vineyard for a break, or a detour into New Preston Village to see the waterfall. This route is best for cyclists who are comfortable with longer distances and varied terrain, and who appreciate quiet, scenic roads.

Planning your visit

Starting your ride from Southbury means you'll be navigating public roads through rural Connecticut to reach the main Lake Waramaug loop. While specific parking details for Southbury aren't provided, consider Lake Waramaug State Park as a key point of interest along the route, offering picnic areas. The roads around the lake are generally quiet, especially on weekdays, making for a more enjoyable experience. The area is particularly stunning in the autumn when the vivid fall foliage reflects beautifully in the lake, though it can also be a popular time for sightseers.

Trail details

  • Distance: 59.2 miles (95.3 km)
  • Elevation gain: 2942 feet (897 metres)
  • Difficulty: moderate
  • Estimated time: 4 hours and 28 minutes

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