Downtown Chestertown, New York







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Piano Shop in Chestertown, New York





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When you purchase a Shop Downtown Discount Card, you help support your neighbors, local economy and the American Cancer Society's mission to save lives, celebrate lives and lead the fight for a world without cancer. You also can get great savings on a variety of products and services every time you patronize a participating member. It's a win/win situation.

The American Cancer Society does not endorse any product or service.

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Things to do in Chestertown, New York

Main Street of old Downtown Chestertown speaks to once what was and what could be once again. As Chestertown the community gathers, it leaves a pocket of opportunity for small business owners to come in and set up shop.Take a few minutes to explore what each downtown has to offer by viewing our directory below.

Downtown Chestertown is the place to buy jewelry offered by downtown merchants with a wide variety of lovely earrings, necklaces, bracelets and of course diamond rings. You are sure to find the top artisan brands and jewelry maker that brings a special touch to each piece offered.

Downtown Chestertown can warm you up on a cloudy day or simply offer your daily perk by visiting your local coffee shop. Quality, purity and punch are targeted with coffee beans curated globally and locally roasted while being served fresh as it is made right in front of you. Order up!

Downtown Chestertown gives several options to find the right piece of art as it takes time and a diligent effort to get just the right piece. Shopping for art downtown is the best way to locate your next purchase.

Downtown Chestertown thanks the collection of small business owners who devote their time and energy to make shopping downtown a great experience. Inventory offered downtown is shopped by the merchant buyer to bring the best products to your neighborhood.

Why do you love downtown?

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.

Alison Barlow
Charming, lovely downtown. Love the antique shops!

Michelle Reesey
Haven't been there yet. Trip is planned in April.

Sking King
I love walking through downtown when the sun finally comes out. You can get a great organic meal at one place, yummy sushi nearby, and awesome beer. Not to mention the Criterion has fabulous shows.

Michelle Goodrich
Nice Shops

Restaurants in Chestertown, New York


Anywheres
6332 State Route 9
Downtown Chestertown



Downtown Chestertown Hotels

Finding the best hotel in Downtown Chestertown can make or break the experience of your entire trip. Take a few minutes to explore what each hotel has to offer by viewing our directory below. Here are some tips to consider:

Bring an actual credit card to avoid deposits and pre-authorizations consuming money in your checking account which will reduce your available balance. Hotels that accept paper cash often ask for a hefty deposit to cover potential damages in your room leaving you scrambling to find an ATM.

Ask to be shown a room before you check-in which signals the front desk agent to show the best room available to sell it right away. This can put you in the best room available at that time and gives you the ability to check for cleanliness, smells and sounds before transacting with the hotel.

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.


The Fern Lodge
 46 Fiddlehead Bay Rd