Downtown Chestertown, New York

Discover shopping, dining, and accommodation in downtown Chestertown.

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Shop Downtown Discount Card

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

Always find a reason to email the front desk manager in hotels that you plan to visit again. Tell them what they did right and express your plans to stay again and ask what opportunities there might be for frequent discounts or upgrades on your next visits. If you become friends with the manager, you just might get the friends and family rate some day.

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.

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 micro breweries have popped up in downtown corridors to quench the thirst of local or traveller whos is looking for a one-of-a-kind experience for suds brewed on site. If you are looking for a light beer or something randy and dark, you are sure to find a wide assortment of options to choose from.

Chestertown has so many great reasons to shop downtown as local merchants have come together to offer a wide selection of artisan gifts and foods that you are sure to find something for everyone on your shopping list of gifts. Shopping options are plentiful and all inventory is hand selected by the shop owner and then yourself so you are sure to find something special that has your style and likes in mind.

Chestertown brings a custom fit every time a shoe is bought locally. Nothing beats the hands on experience of shoe shopping to add to your collection of Men's, Women's and Children's shoes. Try them on, walk around and make sure you have the best fit as every manufacturer is a bit different on sizing.

Why Do You Love Downtown?

Snow Charpentier

It's grown and changed so much since I moved away for a few years and came back. Great to see a lot of smaller businesses expanding and hoping to contribute to the growth of downtown Medford.

Angela Shields

I will be visiting Ashland for the first time this coming weekend! I have heard from numerous people what a great town it is and how much I will like it. Very excited to check it out and do some shopping!

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 .

Randy Swansen

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

HILDA SMITH

It has some unique stores.

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