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Explore Chestertown, NY: A Charming Southern Adirondack Community

Large rooster statue outside of a restaurant in Chestertown NYChestertown 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.

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Chestertown, NY Listings
the outside of friends lake inn during the evening
Friends Lake Inn
Chestertown, NY
Friends Lake Inn in Chestertown, NY, is a charming Adirondack boutique hotel that offers a variety of lodging options and amenities, including steam showers, jacuzzi tubs, private balconies, and roaring fireplaces.
Adirondack-styled bedroom
The Fern Lodge
Chestertown, NY
In the midst of the Adirondacks, overlooking pristine Friends Lake, there stands a wondrous guesthouse where luxurious lodging, sumptuous beds, indulgent baths & unforgettable breakfasts join an atmosphere of rustic elegance & lakeside living.
horseback rider looking down
Circle B Ranch
Chestertown, NY
Circle B Ranch is a family-owned and operated ranch offering trail rides, riding lessons, sleigh rides, and hay rides. Enjoy unparalleled Adirondack mountain views with your experienced guide - there are even pony rides available for the little ones!
Najer Realty
Najer Realty
Chestertown, NY
Personalized guidance in your search for the Adirondack dream--whether it be a ski home in the mountains, lakefront retreat, year-round home or land to build a home. Visit our website for up-to-date listings and ways to contact us for an appointment.
a quaint brown cottage
Twin Pine Lodge
Chestertown, NY
Located on 25 scenic acres of private land in the Adirondacks, Twin Pine Lodge is the premier choice for comfortable and affordable accommodations year round. The property features both authentic log homes and cozy, rustic cottages.
C+C Adirondack Snowmobile Tours
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 exiting trip. We offer a range of riding that is suited for everyone from the beginner to the most advanced rider.
a small greenish cabin
The Lakeside at Loon Lake
Chestertown, NY
Relax in the serene Adirondack Mountains and be close enough to all the activities. The Lakeside at Loon Lake lodging is only 15 minutes from Lake George Village and 15 minutes from the Gore Mountain Ski Area and Mountain Biking Center.
music graphic
The Carol Theater
Chestertown, NY
See a variety of live musical performances and other shows at the historic Carol Theater in downtown Chestertown from June through September. This theater is a huge asset to the Chestertown area, providing exceptional entertainment for the community.
Chestertown Farmers' Market
Chestertown, NY
Spring, late summer, and early fall are perfect seasons for visiting farmers' markets. From the small, mom-and-pop stand at the corner, to the large, organized market with multiple vendors and extensive selections, it is definitely worth the trip.
Crossroads Outdoors Country Store and Sport Shop
Chestertown, NY
Gear up for your Adirondack adventure at the Crossroads Outdoors Country Store and Sport Shop in Chestertown, NY. The local store features a variety of great products as well as a deli and ice cream.
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, bicycling, hiking, snowshoeing, ice skating, snow tubing, and 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, with a wide range of activities and opportunities for skill development.
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. Looking for added excitement? Try one of their night time golf outings by flashlight!
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 shop features an old-fashioned setting that is comfortable and nostalgic.
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 Lake, Chestertown, Schroon Lake, and Brant Lake.
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. They also offer live music entertainment and a wide selection of craft beers at the bar.
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. Farm-to-table meals are provided, and well-behaved dogs are welcome.
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 menus include tasty tapas and appetizers, seafood, steaks, and great craft beers from the region.
Three Lakes Ride
Visit the beautiful lakes of the Southeastern Adirondacks along the 33.2-mile Three Lakes Ride. Beginning in Chestertown, NY, this bike route passes by Brant Lake, Schroon Lake, and Loon Lake. It also features a mix of flat and rolling terrain.
Chester-Horicon Health Center
Chestertown, NY
Serving patients of all ages, the Chester-Horicon Health Center is part of the Hudson Headwaters Health Network family. The community medical center provides a variety of health care services, such as family practice, same day appointments, and more.
Conway's Lake Manor
Chestertown, NY
Year round resort with free internet, private beach area, BBQ, air conditioning, and more! Just a 5 minute drive from Interstate 87.
Gallo Realty ~ Locally Owned & Operated ~ We Know the Area!
Chestertown, NY
Specializing in Lakefront and Vacation Home Sales and Rentals on Brant, Schroon, Loon and Friends Lake. Open 7 days a week for the professional service you deserve! Located 1/4 mile off Exit 25 of I-87... just 20 minutes north of Lake George!
The Adirondack Ramblewood House Rental with Beach/Dock
Chestertown, NY
Beautiful 6 bedroom 3 bathroom house. Large party/reception hall available. Do it yourself party/reception and save money.
The Original Lincoln Logs
Chestertown, NY
The log home. What could be more authentically American? And no one makes log homes quite the way we do. Learn how our products and services make your dream a reality.