Chestertown

The Main Street Ice Cream Shop in Chestertown, a yellow two-story building with white trim, arched windows with shutters, and a porch entrance. Signboard advertising clothing boutique, gifts, cards, toys, pies, ice cream cakes, and a restaurant.
Illustration of St. James Catholic Church in Chestertown, New York, with surrounding trees and a circular garden in front.

Adirondack and then some.

Tucked between quiet lakes, Chestertown offers the kind of unhurried escape that’s hard to find in busier destinations nearby.

Spend your days hiking forest trails, paddling calm waters, or exploring year-round outdoor adventures—from summer kayaking to winter snowmobiling. Then settle into the simple pleasures: a local café, a scenic sunset, the sound of wind through the trees. Just minutes from Lake George yet worlds away in feel, Chestertown delivers an authentic, restorative Adirondack experience.

  • Loon Lake Marina

    The spot for all things boating on Loon Lake. Sales and rentals with all the equipment needed for a great day out on the water

    Pull up to the dock
  • An iced coffee sits on a ledge with the Two Sparrows Coffee Company logo artwork behind it.

    Two Sparrows Coffee Co.

    A community centered coffee shop with a variety of espresso drinks, drip coffee, fruit smoothies, grab and go style snacks and baked goods, and more!

    Coffee and Cheer

  • Hometown Charm

    The perfect gift is just inside the doors of Hometown Charm. Paintings, candles, and Adirondack crafts that will spruce up any interior.

    Charming gifts and fine art

  • Loon Lake Public Beach

    Right off Rt. 8 it’s the perfect sandy spot to dip your toes in the water.

    Ready to swim?

  • The Carol Theatre

    Movies, music, live events, check out all that The Carol has planned for the season.

    It's showtime

  • Friends Lake

    Visit Friends Lake for a quiet escape from the everyday. Try the wine selection at The Friends Lake Inn, or take a boat ride from The Fern Lodge.

    Get away

  • Farmer's Market

    Wednesdays in the summertime, vendors from all over the region gather in front of the Chester Town Hall and sell fresh produce, crafts, and more.

    To market, to market

  • The Remington on Main

    Classic American Fare with a relaxed atmosphere. Right on Rt. 9 in the heart of Chestertown.

    Let's eat!

  • The Loon Restaurant

    Stop into The Loon for great eats and Adirondack atmosphere. Right off Route 8 headed west from Chestertown proper.

    Check out the Loon

Creature comforts without the crowds.

If you’re looking for a true Adirondack experience that feels less discovered, it’s kind of a hidden gem. Chestertown is close to the Northway, surrounded by lakes, forests, and mountains—but it feels calm and uncrowded. Here, you recharge instead of rush.

  • Take I87 to Exit 25. Turn left off the exit, onto Route 8. Continue past the school on your left and then Dynamite Hill on your right to a stop light. Turn Left onto Route 9.

  • Stewart’s on Route 8 near exit 25 for convenience items and dairy. Tops Market in the heart of town for a full shop.

  • The Chestertown Farmer’s Market, open Wednesdays from 9am–2pm is held in front of the Chester Town Hall on Route 9. It’s amazing.

A circular sign hanging from a wooden pole reads 'PANTHER MOUNTAIN TRADERS, EST 2018, CHESTERTOWN, NEW YORK.' In the background, a log cabin with a metal roof, surrounded by a gravel yard with rocks and bushes, and trees with some autumn foliage.
Chesterstown patch with mountain, trees, and water scene.