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

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.

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.

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.

Things To Do

Chestertown has that special dining venue and you are sure to find something to please with numerous meals served to satisfy each palette. A wide variety of restaurants and delis are available to choose from with a nice selection of entrees and especially desserts.

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 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.

Why Do You Love Downtown?

Darcie Maassen

I love Downtown because I love the beautiful historic buildings. It's a very pretty area aesthetically. I also appreciate the great variety of delicious dining within a small area. Favorites include Capers, Pomodori, Paisanos, Bricktowne Brewery, Elements Tapas bar, Porters, Larks and 4 Daughters. They are all within 4-5 blocks!

carl barbieri

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

Terri Simon

I love to dine at the Inn and to shop at specialty shops.

Darby

Visiting in July for the 1st time!

Michelle Reesey

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

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