4.7
(2150)
13,850
hikers
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
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
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.