Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Hikes
United States
New York
Warren County

Chestertown

The best walks and hikes around Chestertown

4.7

(6)

87

hikers

11

hikes

Hiking around Chestertown offers access to varied landscapes, including riverfront paths and forested trails. The region is characterized by its position near the Chester River, providing opportunities for walks along waterways. Elevation changes are generally mild, with some routes featuring gradual ascents. The terrain primarily consists of established paths through woodlands and open areas.

Best hiking trails around Chestertown

  • The most popular hiking route is Cat and Thomas Mountain Loop, a 5.6 miles (9.0 km) trail that takes 3…

Last updated: May 31, 2026

2

hikers

#1.

Cat and Thomas Mountain Loop

9.01km

03:05

340m

390m

Embark on the Cat and Thomas Mountain Loop for a rewarding hike that spans 5.6 miles (9.0 km) with a moderate difficulty rating. You will gain 1116 feet (340 metres)…

Navigate with device

Send to Phone

Save

Moderate

2

hikers

5.47km

01:43

260m

80m

The Cat Mountain Blue Trail offers an easy hiking experience, covering 3.4 miles (5.5 km) with an elevation gain of 858 feet (261 metres). You can expect to complete this…

Easy
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Embark on the Pack Demonstration Forest Loop Trail, a moderate hike that guides you through dense woodlands, past picturesque lakes and wetlands. This 7.0-mile (11.3 km) route features a gentle…

Moderate

3.7

(3)

26

hikers

Hike the moderate Cat and Thomas Mountain Loop for 7.4 miles (11.9 km) to enjoy panoramic views of Lake George and the Adirondacks.

Moderate

5.0

(1)

13

hikers

4.79km

01:32

210m

210m

Easy 3.0-mile hike to Thomas Mountain Lookout with panoramic views of Lake George and the Adirondacks.

Easy
Sign up for free to see 7 more hikes around Chestertown.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Chestertown

Road Cycling Routes around Chestertown

Cycling around Chestertown

Tips from the Community

Robert Fuchs
July 25, 2025, View of Lake George from Cat Mountain

bring lots of mosquito spray! amazing views from the top but can be painful insect experiences on the way

0

0

At this junction you can proceed west up the Richard Hayes Phillips Trail to the summit of Thomas Mountain, South along the Blue Trail to Cat Mountain via a collection of ponds, or northeast along the Blue Trail to the Thomas Mountain Trailhead.

0

0

You get a great view of Cat Mountain, the southern tip of Lake George and the Adirondack Mountains from the overlook.

0

0

The scenic marshy lakes you find along the eastern side of Thomas Mountain are unnamed. They are tributaries that flow into Edgecomb Pond.

0

0

You will find panoramic view of Lake George from the summit of Cat Mountain. The trails up the mountain are well maintained and well marked.

0

0

Schedule time to enjoy this vista. Great place for a meal break.

0

0

Bonnie24
October 31, 2019, Edgecomb Pond

Magnificent lake, serves as a drinking water reservoir. Swimming and fishing prohibited.

Translated by Google

5

0

Frequently Asked Questions

What kind of terrain can I expect on hiking trails around Chestertown?

Hiking around Chestertown offers a mix of riverfront paths, forested trails, and wetland boardwalks. The terrain is generally mild, with gentle hills and established paths through woodlands and open areas. You'll find diverse ecosystems, from brackish tidal marshes to upland forests.

Are there any easy hiking trails suitable for beginners or a relaxed stroll?

Yes, Chestertown has several easy options. The Cat Mountain Blue Trail is an easy 3.4-mile path. Additionally, the Wayne Gilchrest Trail (Chestertown Rail Trail) offers a paved, accessible 2.1-mile route along the Chester River. Within the Eastern Neck National Wildlife Refuge, trails like the Bayview/Butterfly trail and Duck Inn Trail are also accessible and offer gentle experiences.

Where can I find trails with scenic views or natural features?

For scenic views, the Eastern Neck National Wildlife Refuge is highly recommended. Trails like the Tidal Marsh Overlook provide views of tidal marshes, while the Bayview/Butterfly trail offers vistas of the Chesapeake Bay. The Boxes Point Trail leads to the Chester River bank, a good spot for bald eagle sightings. The Wayne Gilchrest Trail also provides excellent river views as it follows the Chester River.

Are there any family-friendly hiking options in the Chestertown area?

Absolutely. The Lawrence Wetlands Preserve, located near historic Chestertown, features trails and boardwalks designed for observing wetland wildlife and understanding watershed ecology, making it an educational and accessible option for families. The paved Wayne Gilchrest Trail is also suitable for families, including those with strollers or wheelchairs.

Can I bring my dog on the hiking trails around Chestertown?

Many trails in the Chestertown area are dog-friendly, but it's always best to check specific regulations for each location. For instance, the Wayne Gilchrest Trail is generally welcoming to leashed dogs. However, national wildlife refuges like Eastern Neck often have specific rules regarding pets to protect wildlife, so verify their current pet policy before visiting.

What kind of wildlife can I expect to see while hiking?

The region is rich in wildlife, especially birds. The Eastern Neck National Wildlife Refuge is a crucial staging site for migratory birds, with over 240 species, including bald eagles and tundra swans. You might also spot various wetland wildlife, butterflies, and other native species in areas like the Lawrence Wetlands Preserve.

Are there any loop trails available for hiking?

Yes, there are several loop options. The Cat and Thomas Mountain Loop is a moderate 5.6-mile trail, and the Pack Demonstration Forest Loop Trail is a 7.0-mile route through forested areas. Within the Eastern Neck National Wildlife Refuge, several trails can be combined to form loops, offering diverse experiences.

What do other hikers enjoy most about hiking in Chestertown?

The area is highly rated by the komoot community, with an average score of 4.7 stars. Reviewers often praise the diverse landscapes, from river views to tranquil forested paths, and the opportunities for wildlife spotting. The accessibility of many trails and the gentle nature of the terrain are also frequently highlighted.

Are there any accessible trails for people with mobility challenges?

Yes, Chestertown offers accessible options. The Wayne Gilchrest Trail (Chestertown Rail Trail) is a paved, wheelchair-accessible path. Within the Eastern Neck National Wildlife Refuge, the Bayview/Butterfly trail and the Duck Inn Trail feature accessible surfaces and boardwalks, designed to be enjoyed by all visitors.

Where can I find parking for hiking trails in Chestertown?

Parking is generally available at trailheads and nature preserves. For instance, the Wayne Gilchrest Trail has access points with parking, including at Wilmer Park. The Eastern Neck National Wildlife Refuge and Lawrence Wetlands Preserve also provide designated parking areas for visitors. It's always advisable to check specific location details before your visit.

Are there any notable natural landmarks or preserves to explore?

Definitely. The **Eastern Neck National Wildlife Refuge** is a significant natural attraction, offering a mosaic of habitats and crucial bird staging sites. The **Lawrence Wetlands Preserve** provides an accessible urban nature experience with diverse ecosystems. Both offer trails to explore their unique natural features.

What is the best time of year to go hiking in Chestertown?

While hiking is possible year-round, spring and fall generally offer the most pleasant conditions with mild temperatures and beautiful scenery. Spring brings blooming flora and active migratory birds, while fall showcases vibrant foliage. Summer can be warm and humid, and winter offers a quieter experience, especially for spotting waterfowl.

Most popular routes around Chestertown

Easy hikes around Chestertown

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Hikes in other regions.

Lake GeorgeBolton LandingWarrensburgSiamese Ponds WildernessRalph Road State ForestGlens FallsGlens Falls NorthCharles Lathrop Pack Demonstration ForestWest Glens FallsLake GeorgeLake LuzerneNorth CreekPottersville

Nearby adventure guides

Things to Do in Charles Lathrop Pack Demonstration Forest

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy