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Routes
Hiking trails & Routes
United States
Connecticut
Lower Connecticut River Valley Planning Region
Middletown

Herbert's Way Trail

Easy

4.7

(2150)

13,850

hikers

Herbert's Way Trail

01:07

4.06km

70m

Hiking

Embark on an easy 2.5 miles (4.1 km) hike along Herbert's Way Trail, a route that guides you through a diverse and scenic landscape. You will experience a gentle elevation gain of 232 feet (71 metres) over approximately 1 hour and 6 minutes, making it perfect for a relaxed outing.…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

1

1.48 km

Paddy Hill

Highlight • Summit

B

4.06 km

End point

Parking

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Way Types & Surfaces

Way Types

3.48 km

314 m

174 m

< 100 m

Surfaces

3.47 km

366 m

123 m

< 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.

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Weather

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Today

Saturday 9 May

14°C

7°C

96 %

Additional weather tips

Max wind speed: 10.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access Herbert's Way Trail?

You can find parking available at Highlawn Forest, which is located near the Middletown/Middlefield border in Connecticut. The trailhead is easily accessible from the parking area.

Is Herbert's Way Trail dog-friendly?

Yes, this trail is generally dog-friendly. However, it's always a good practice to keep your dog on a leash and clean up after them to ensure a pleasant experience for all visitors and to protect the local wildlife.

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

The trail offers a varied experience throughout the year. Spring and fall are particularly beautiful with changing foliage and comfortable temperatures. Summer is also pleasant, but be mindful of potential marshy areas. Winter hiking is possible, but conditions may vary, especially on the planked sections over wet ground.

Are there any permits or entrance fees for Highlawn Forest?

No, there are no permits or entrance fees required to access Highlawn Forest or hike this trail. It is part of the Connecticut Forest & Park Association (CFPA) network, which aims to provide accessible outdoor experiences.

Is this trail suitable for beginners or families?

Absolutely! This route is described as flat and easy, making it great for young or beginner hikers. There's even a handicapped-accessible "Discovery Loop" with a crushed bluestone path near the trailhead, perfect for strollers or wheelchairs.

What kind of scenery and terrain can I expect on the trail?

You'll experience diverse scenery, including second-growth forests, conifer plantations, mixed hardwood forests, and red maple swamps. The terrain is generally flat, though some areas can be rocky. A notable feature is long stretches of planking over marshy ground, and an impressive evergreen pine plantation with soft pine needles underfoot. You'll also pass a pond and a large vernal pool with an observation platform.

Is Herbert's Way Trail a loop?

The main Herbert's Way Trail is part of a larger trail system in Highlawn Forest. While the specific route described is not a full loop, the network allows for various loop configurations by connecting with other trails within the forest.

Are there any notable features or points of interest along the way?

Yes, the trail offers several interesting features. You'll pass by Paddy Hill, an outdoor amphitheater, and a unique "poet-tree" where visitors can create "family stone poems." Keep an eye out for historical elements like old stone walls and foundations from its past as a Christmas tree farm and agricultural land.

Does this route connect with other trails?

Yes, the route is part of a larger network within Highlawn Forest. Approximately 29% of the route also passes through sections of the Discovery Trail, offering opportunities to explore further.

What should I wear or bring for this hike?

Given the varied terrain, including marshy areas with planking, sturdy waterproof hiking shoes are recommended. Dress in layers suitable for the season, and consider bringing insect repellent, especially during warmer months. Don't forget water and snacks, as there are no facilities on the trail itself.

Is any part of the trail accessible for wheelchairs or strollers?

Yes, near the trailhead, there is a dedicated "Discovery Loop" that features a crushed bluestone path, making it accessible for wheelchairs and strollers. This loop provides an easy and enjoyable experience for everyone.

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