Downtown Chestertown, Maryland

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

Comfort Suites Chestertown

160 Scheeler Rd

Chestertown, Maryland

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road

Chestertown, Maryland

Hotel Tips

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.

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.

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!

Things To Do

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 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 a great collection of barber shops to choose from if you want to take a little off the top, get a clean shave or to trim your moustache or beard. Take a moment to consider buying some styling gel, beard oil or wax and always tip well.

Why Do You Love Downtown?

Heather Anne Hopfinger

You do not have to walk far for a movie or some place great to shop or workout

Patricia Majewski

So quaint and fun!

Dorothy Wilson

Unique shopping-love the atmosphere

Jennifer Wagner

First time downtown!

Carrie Homier

6 women looking to explore the area. We will be there Feb. 18th. Whatever you can do to open our wallets easier and more economical would be much appreciated and fun! Thank you.

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