Downtown Chestertown, New York Main Street Shops, Restaurants & Hotels

Improving the Economic Vitality of Our Downtowns

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We are seeking partnerships with forward-thinking city officials and business leaders to replicate
their downtowns and launch immersive virtual cities together.

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Hotels

The Fern Lodge
46 Fiddlehead Bay Rd
Chestertown, New York

Hotel Tips

Ask to be placed opposite of any roadways. Road noise can be a constant source of pollution which may not be a noticeable problem during the day but reveals itself at night. Don't be afraid to request a room change to get a better sleep.

Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.

Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.

Things To Do

Chestertown brings musicians together and finding your local musical instrument shop can be a great way to get to try new and used guitars. Be sure to start your search downtown if you are looking to upgrade, trade-in or add to your collection.

Chestertown hosts several events per year for your listening enjoyment but visit your piano shop to learn how to play and possibly purchase your grand, upright or digital piano. Don't forget the specialty work involved such as tuning and moving which are performed by skilled technicians.

Chestertown visitors are always welcome and you will receive exceptional service from local merchant-owners as opposed to staff at the big box retailers. We take the extra time to make sure that you how to make best use of your purchase and that you get exactly what you need.

Why Do You Love Downtown?

Caren Murphy
Cute shops, great crab cakes, friendly.

Mary jo bos
My daughter moved to Talent this summer and I came to visit her for Christmas. She took me to the downtown Ashland area to shop. I love fall the shops and the friendliness .

Taree Hines
Historic

Schuyler Judd
Interesting people and shops!

Christy Richards
Because I love to shop local and the stores and owners make your visit welcoming inviting you to return again with a smile on their face.

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