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Downtown Chestertown, New York





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Fight Cancer


ShopDowntown.org and the American Cancer Society (ACS) have launched a new program that provides discounts at local stores while raising money to fund cancer research, programs and services. Shoppers who donate $20 or more to the American Cancer Society are eligible to receive a free Shop Downtown Discount Card. Simply make a donation online, get your receipt verified, and receive your digital discount card to save up to 15% off at participating businesses.

When you get a Shop Downtown Discount Card, you help support your neighbors, the 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 business. 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 brings meaning to leisure time while enjoying the local yarn shop and wandering through in amazement with the different fibers and vast array of colors. Signing up for a class is easy and fun and serves as a great getaway for a few hours to enjoy the company of fellow knitters.

Downtown Chestertown has the perfect game shop for both young and old. Your friends and family will enjoy hours of entertainment with a wide selection of board games, card games and games of skill. A perfect stop for travellers with kids and those seeking a new adventure for game night.

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 shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.

Why do you love downtown?

Sharon Skipton
Will be there in a week. Looks like a great town!

Kathy Tidmarsh
will be staying in Aug. 2017 and looking forward to enjoying your town

Randy Swansen
We haven't been before, but we're looking forward to coming down next week!

carl barbieri
were there on business at least 7 times a year ,We just love downtown medford

Jerretta O'Haver
Heading Downtown in August 2017 !

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:

Upon check-in, slip the desk agent a tip and ask for the best room they can find at your current booked rate. Often times a quick $10 or $20 bill can go a long way towards the mood of the person who directly decides where you lay your head for the night.

Call ahead to make sure your reservation is still active and rebook if there are any price drops or changes in number of people staying with you. Another cost saving tips is to bundle the stay with airport parking and shuttle to avoid hefty fees.

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.


The Fern Lodge
 46 Fiddlehead Bay Rd