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Routes
Hiking trails & Routes
United States
New York
Chautauqua County

East Side Overland Trail

Hard

3.1

(15)

75

hikers

East Side Overland Trail

14:37

53.6km

840m

Hiking

Hike the difficult 33.3-mile East Side Overland Trail, gaining 2765 feet through forests, ravines with waterfalls, and wildflower meadows.

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Waypoints

A

Start point

Parking

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22.9 km

Boutwell Hill State Forest

Nature Reserve

24.9 km

Arab Hill Pond

Lake

33.8 km

Canadaway Creek Wildlife Management Area

Nature Reserve

37.3 km

Dibble Hill Pond

Lake

B

53.6 km

End point

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Way Types & Surfaces

Way Types

25.9 km

13.9 km

13.5 km

206 m

Surfaces

39.7 km

8.70 km

5.05 km

< 100 m

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Elevation

Elevation

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Weather

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Today

Wednesday 27 May

24°C

13°C

0 %

Additional weather tips

Max wind speed: 13.0 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 the East Side Overland Trail?

The trail is part of the larger Overland Trails system in Chautauqua County, and specific parking areas would typically be found at trailheads. While the research doesn't specify exact parking locations, it mentions a pond roughly two miles from one of the parking areas, indicating designated access points exist.

Is the East Side Overland Trail dog-friendly?

Yes, leashed dogs are welcome on the trail, making it a good option for pet owners.

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

The trail features wildflowers like daisies and milkweed blooming in meadows, suggesting spring and summer offer vibrant scenery. However, the heavily wooded forests with maples, cherry, evergreen, and hemlock trees would also provide beautiful views in the fall. Consider seasonal conditions for mud or slippery wooden bridges.

Do I need a permit or pay an entrance fee for this trail?

The provided information does not indicate any requirements for permits or entrance fees to access the East Side Overland Trail.

What kind of terrain can I expect on the trail?

You'll encounter diverse natural surfaces, including singletrack paths made of gravel, dirt, and leaf litter. There are also wooden bridges, which can be slippery when wet, and occasional muddy sections. Expect uphill climbs, clear streams, and sections alongside meadows and through heavily wooded forests.

How difficult is the East Side Overland Trail?

The trail is generally rated as "Blue difficulty" or "Intermediate" for hiking. While it includes a long, uphill climb in some areas, it's considered less popular with lighter traffic, offering a more peaceful experience.

Are there any notable natural features or landmarks along the route?

Yes, the trail features pretty ravines with miniature waterfalls, clear streams, meadows with wildflowers, and heavily wooded forests of maples, cherry, evergreen, and hemlock trees. Near a pond, you might also spot wind turbines, adding a modern element to the natural landscape. The trail also passes through Harris Hill State Forest.

Is there water available on the trail?

There is a pond roughly two miles from one of the parking areas, which has a water pump. However, the water from this pump is non-potable, so you should carry your own drinking water.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the East Side Overland Trail, Blue Trail, Red Trail, Yellow Trail, and Earl Cardot Eastside Overland Trail (Blue 1).

What makes this trail unique or a 'hidden gem'?

The East Side Overland Trail is part of the larger Overland Trails system, offering over 40 miles of trails in Chautauqua County. It's known for its diverse ecosystems, from ravines and streams to wildflower meadows and dense forests. It's also less popular, providing a more peaceful hiking experience, and is well-maintained with clear blue blazes for navigation. The trail is named in honor of Earl Cardot, who was instrumental in establishing many local forest plantations.

How long does it typically take to hike this trail?

The full East Side Overland Trail is approximately 53.5 kilometers (33.2 miles) long. A typical hike of this distance and difficulty (rated as difficult) would take around 14 hours and 36 minutes to complete.

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