Downtown Chestertown, New York
Discover shopping, dining, and accommodation in downtown Chestertown.
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ShopDowntown.org Discount Card Program
The ShopDowntown.org Discount Card Program encourages local shopping by offering exclusive savings at participating downtown businesses. Shoppers can obtain a discount card by donating $20 or more to the American Cancer Society, unlocking deals of up to 15% off at local stores. The program supports small businesses, funds community health initiatives, and helps strengthen the local economy, making it a win-win for both merchants and consumers.
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Hotels
The Fern Lodge
46 Fiddlehead Bay Rd
Chestertown, New York
Hotel Tips
Other sources of noise can be opening and closing trash dumpsters and also during collection by garbage trucks. Another great question is if they have any renovation plans, or underway that could affect your ability to relax. Pack earplugs and eyeshades!
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.
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 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.
Chestertown makes shopping for wine and other spirits easy by bringing an incredible collection sourced from local, regional well-known producers from around the World. Hit the wine tasting events and stock up on your favorite choice to be shipped home for your convenience.
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?
Susan Sunday
Adorable - been 1x and going back tomorrow with my friends
Kate O'Rorke
We love the amazing shops and restaurants. The city is so clean and everyone is friendly and welcoming.
Tracy Friend
It's adorable and friendly. Love to visit all the shops.
Kathleen Gerds
Looking forward to Ashland downtown. Theater and shopping here we come.
Kara Braud
Beautiful place!
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