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United States
Connecticut
Northwest Hills Planning Region

Lake Winfield Recreation Area

The best walks and hikes in Lake Winfield Recreation Area

4.3

(10)

80

hikers

23

hikes

Hiking trails in Lake Winfield Recreation Area Plymouth CT explore a landscape of dense woodlands, rolling hills, and lakeside paths. The region is part of Connecticut's Blue-Blazed Hiking Trail system, featuring sections of the Mattatuck and Tunxis trails. The terrain consists of well-marked forest paths with some rocky sections and moderate changes in elevation. The area encompasses a 9 to 16-acre lake, providing a scenic water feature.

Best hiking trails in Lake Winfield Recreation Area

  • The most popular hiking route…

Last updated: June 28, 2026

5.0

(1)

5

hikers

#1.

Mile of Ledges and Tory Den Trail

7.13km

02:01

110m

110m

Moderate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.

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Moderate

4.5

(2)

6

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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4

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

3.0

(1)

2

hikers

2.39km

00:37

10m

20m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

1

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Popular around Lake Winfield Recreation Area

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Tips from the Community

Scott
December 4, 2023, Tory's Den

In the woods of Burlington lies the impressive rock formation known as the "Tory Den," where British sympathizers once hid. This massive rock structure, with nooks, crannies, and a small escape hole, reveals its historical secrets amid blackened walls and rock ledges.

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Frequently Asked Questions

Are dogs allowed on the trails in the Lake Winfield area?

Yes, dogs are generally welcome on the hiking trails around Lake Winfield Recreation Area, but they should be kept on a leash. It's always a good practice to bring water for your pet and to clean up after them to help preserve the natural beauty of the trails.

Are there any easy, family-friendly hikes available?

Absolutely. The area offers several easier hikes suitable for families. A great option is the Leatherman Cave – Eagle Rock loop from Watertown. It's a relatively short trail that still provides a sense of adventure and rewarding valley views from an overlook.

Can I see any waterfalls on the hikes?

Yes, the region is home to some beautiful waterfalls. The Mattatuck Trail leads to Buttermilk Falls, one of the state's highest natural waterfalls. For a specific route that includes a waterfall, consider the Beaver Marsh – Freeman Hill brook Waterfall loop, which takes you through serene forests to a charming cascade.

Are there any circular or loop trails?

Many of the best hikes in the area are loops, allowing you to enjoy a varied journey without retracing your steps. A notable choice is the Black Rock Lookout loop from Watertown, which offers a rewarding climb to a rock face with panoramic views of the surrounding towns.

What is the best way to get to the trailheads?

Driving is the most convenient way to access the various trailheads around the Lake Winfield Recreation Area. There is parking available at the main recreation area and near the start of major trails like the Tunxis and Mattatuck. Be sure to check your specific route for the best starting point.

Are there any hikes with historical significance?

Yes, the trails are rich with history. The Tory's Den loop from East Plymouth Historic District is a must-do. This hike on the Tunxis Trail takes you to a rock formation that served as a hideout for Loyalists during the Revolutionary War, offering a fascinating glimpse into the past.

How many hiking trails are in the Lake Winfield area?

There are over 10 miles of marked trails in the Plymouth area, which are part of the larger Blue-Blazed Hiking Trail system. Komoot features more than a dozen curated routes, ranging from easy lakeside walks to more moderate forest hikes.

What is the terrain like on the trails?

The terrain is varied. You'll find everything from gentle, flat paths around the lake to more rugged and rocky sections on the Mattatuck and Tunxis trails. Most routes involve moderate elevation changes through dense woodlands and past scenic overlooks.

What do other hikers enjoy about the Lake Winfield area?

The area is highly rated by the komoot community. Hikers often praise the well-marked Blue-Blazed trails, the mix of serene forest scenery, and the unique historical and natural features like Tory Den and the various waterfalls.

Are there any challenging hikes with caves?

For a more challenging trek, the trail to Leatherman Cave is an excellent choice. The Leatherman Cave loop from Watertown involves some steep climbs and rocky ridges, but rewards you with a visit to the historic cave and beautiful scenic views.

What other activities are available at the Lake Winfield Recreation Area itself?

Besides hiking, the 33-acre recreation area offers plenty to do. There is a 16-acre lake perfect for fishing and non-motorized boating like kayaking. You'll also find a playground, a picnic gazebo, and courts for tennis and pickleball, making it a great spot for a full day of outdoor fun.

Most popular routes in Lake Winfield Recreation Area

Easy hikes in Lake Winfield Recreation Area

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