Downtown Chestertown, Maryland

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

Comfort Suites Chestertown

160 Scheeler Rd

Chestertown, Maryland

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road

Chestertown, Maryland

Hotel Tips

Elevators are notorious for being a nuisance so ask to be roomed on the top floor and as far away as possible. Most hotels book nearby rooms last so hopefully they have availability elsewhere.

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.

Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.

Things To Do

Chestertown helps you expand your skills and learn some new ways to expand your artisan flare? Sign up for classes at your kitchen supply store, yarn shop, art and craft shop and photo gallery. You'll be having great fun with your new friends as you you take on that next project.

Chestertown offers on-the-go dining when you visit your favorite food truck. Pick up some corn tortilla tacos with freshly made pico with a fresh squeeze of lemon to give your day a boost. Food trucks can offer a wide variety of niche ethnic blends.

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.

Why Do You Love Downtown?

Millie

So unique!

Roberta Gomes

it's so quaint!

Judy Caverly

Interesting shops, good restaurants, friendly people.

Jessica L Smith

Love the atmosphere and the people!

Valentina Eagar

Fun and unique shopping and eats

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