Downtown Chestertown, New York

Discover shopping, dining, and accommodation in downtown Chestertown.

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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 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.

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.

Things To Do

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.

Chestertown is the place to go when you want to freshen up or replace your nails. Call ahead to schedule an appointment, pick your colors and style and let the transformation begin. Some salons offer hair styling and coloring as well as lashes and eyebrow coloring.

Chestertown brings the farming community under one marketplace to offer an assortment of locally grown fruit and vegetables. Traditionally, markets are restricted to anything grown so you can expect to see natural whole foods that are sure to please those working on their plant-based diets!

Why Do You Love Downtown?

Liisa Shunn

We love going downtown, because we like to support our local economy. The shops and restaurants we visit -- we have gotten to know the owners, so when our money is spent downtown, we know who benefits. Also? We live only a mile from downtown, so we walk or ride our bikes. No worries about a designated driver or looking for parking. We chose to live in Medford, so of course we want our money to stay in Medford, not going off to some corporate office of a chain store.

Sharon Skipton

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

Crstal Howley

Hoping to enjoy your downtown. This is my first trip!!!

Robby

High quality group of restaurants and wonderful shops! Authentic old fashioned down-town atmosphere brings it all together very well.

Molly MacTaggart

Always love quaint, historic downtown areas, late April will be our first visit to Dillon.

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