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Explore Chestertown, NY: A Charming Southern Adirondack Community

Large rooster statue outside of a restaurant in Chestertown NY

Chestertown is a little community with a big presence. Here you can enjoy a variety of restaurants, take a horseback ride along forested trails, ski miles of cross-country trails, and enjoy a free downhill ski and snowboard area with a rope tow. There's a 9-hole golf course located within Chestertown as well as an 18-hole course in nearby Warrensburg.

When it's time to relax, stroll the main street in search of that special gift or antique treasure. Indulge yourself at an old-fashioned ice cream parlor. Relax and enjoy a simple, uncomplicated lifestyle amid the beautiful scenery of the Adirondacks.

Visiting in the summer? Enjoy the many water activities in the area. Loon Lake near Chestertown offers boating, waterskiing and swimming. Try your hand at bullhead fishing, or enjoy the shimmering sunset on a dock with a good book. The nearby Schroon & Hudson Rivers offer opportunities for whitewater rafting, kayaking, or fly fishing.

Book A Room

a hot tub in a living room with as tone fire place, view of a patio outside
The Fern Lodge
Chestertown, NY
In the midst of the Adirondacks, overlooking pristine Friends Lake, there stands a wondrous guesthouse where luxurious lodging, su... [+More]
C+C Adirondack Snowmobile Tours Logo with a snowmobile in front of a mountain
C+C Adirondack Snowmobile Tours
Chestertown, NY
Our staff of C+C Adirondack Snowmobile Tours has a combined 40+ years riding on the trails, so get ready for an exciting trip. We ... [+More]
the exterior of friends lake inn
Friends Lake Inn
Chestertown, NY
Friends Lake Inn in Chestertown, NY, is a charming Adirondack hotel that offers a variety of room options and amenities, including... [+More]
Green Mansions Golf Club
Chestertown, NY
Located in the Southern Adirondacks, Green Mansions Golf Club features nine challenging holes, plus a driving range and pro shop. ... [+More]
Adirondack PC
Chestertown, NY
Adirondack PC has offices in Chestertown and Queensbury, and provides tech support, website design, computer upgrades, and more. T... [+More]
D&S Adirondack Sealcoating
Chestertown, NY
When you need sealcoating services for your driveway or parking lot, D&S Adirondack Sealcoating in Chestertown, NY can help!... [+More]
Dynamite Hill Recreation Center & Nature Trail
Chestertown, NY
Head on over to the Dynamite Hill Recreation Area for all sorts of fun outdoor activities, including cross-country ski trails, bic... [+More]
Panther Mountain Pub
Chestertown, NY
Located at the Panther Mountain Inn in Chestertown, NY, Panther Mountain Pub specializes in all your pub food favorites and pizza.... [+More]
Posh Primitive
Chestertown, NY
At Posh Primitive, you'll find custom made tents, queen-size beds, fresh linens, and an ideal location in the southern Adirondacks... [+More]
O.P. Frederick's
Chestertown, NY
Located on beautiful Loon Lake in Chestertown at the corner of Routes 8 and 9 O.P. Frederick's offers delicious food in a relaxed ... [+More]
Mountain Hardware
Chestertown, NY
Mountain Hardware in Chestertown has what you need for work around the house, home improvement projects, and more.... [+More]
J.C. Lumber Company
Chestertown, NY
J.C. Lumber Company is a third-generation business here for all your rough and finished lumber needs.... [+More]
Three Lakes Ride
Visit the beautiful lakes of the Southeastern Adirondacks along the 33.2-mile Three Lakes Ride. Beginning in Chestertown, NY, this... [+More]
The Crossroads
Chestertown, NY
Gear up for your Adirondack adventure at The Crossroads, a sport shop and country store located in Chestertown, NY. This family-ow... [+More]
Main Street Ice Cream Parlor & Restaurant
Chestertown, NY
For tasty icy treats, great food, and more, visit the Main Street Ice Cream Parlor & Restaurant in Chestertown, NY. The ice cream ... [+More]
Forest Lake Camp
Chestertown, NY
Forest Lake Camp sits on just over 800 acres in the Southern Adirondacks. The camp offers separate programs for boys and girls, wi... [+More]
North Warren Chamber of Commerce
Chestertown, NY
The chamber directs visitors to local businesses in the North Warren area including the towns of: Pottersville, Loon Lake, Friends... [+More]
The Bullhouse
Chestertown, NY
Located in the heart of Chestertown, NY, The Bullhouse is serving up Latin American cuisine in a casual yet upscale setting. Their... [+More]