Downtown Chestertown, Maryland









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Shop Downtown Discount Card

Discounts For Customers - Support Local Businesses - Fight Cancer

When you purchase a Shop Downtown Discount Card for $10, you help support your neighbors, local economy and the American Cancer Society's mission to save lives, celebrate lives and lead the fight for a world without cancer. You also ensure great savings on a variety of products and services every time you patronize a participating member. It's a win/win situation.

Shop Downtown will contribute 100% of the sale price of each discount card sold through December 31, 2021, to American Cancer Society Relay For Life. The American Cancer Society does not endorse any product or service.









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Things to do in Chestertown, Maryland

Main Street of old Downtown Chestertown speaks to once what was and what could be once again. As Chestertown the community gathers, it leaves a pocket of opportunity for small business owners to come in and set up shop.Take a few minutes to explore what each downtown has to offer by viewing our directory below.

Downtown 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.

Downtown 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.

Downtown 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.

Downtown 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.

Why do you love downtown?

BOB BLACKMAN
Just a fun place to visit.

Tammy Benson
Shopping eating and site seing

Kim Ward
Unique and wonderful shopping.

Alison Barlow
Charming, lovely downtown. Love the antique shops!

Jennifer Moranda
Planning my first trip.

Restaurants in Chestertown, Maryland


Batter Up Restaurant

830 High St
Downtown Chestertown




Downtown Chestertown Hotels

Finding the best hotel in Downtown Chestertown can make or break the experience of your entire trip. Take a few minutes to explore what each hotel has to offer by viewing our directory below. Here are some tips to consider:

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!

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.

Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.