Downtown Chestertown, Maryland

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Discounts For Customers - Support Local Businesses - Fight Cancer




ShopDowntown.org and the American Cancer Society (ACS) have launched a new program that provides discounts at local Southern Oregon stores while raising money to fund cancer research, programs and services. Shoppers who donate $20 or more to the American Cancer Society are eligible to receive a free Shop Downtown Discount Card. Simply make a donation online, get your receipt verified, and receive your discount card to save 5-15% off at participating businesses.

When you get a Shop Downtown Discount Card, you help support your neighbors, the 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 can get great savings on a variety of products and services every time you patronize a participating business. It’s a win/win situation.


Piano Shop in Chestertown, Maryland



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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 can warm you up on a cloudy day or simply offer your daily perk by visiting your local coffee shop. Quality, purity and punch are targeted with coffee beans curated globally and locally roasted while being served fresh as it is made right in front of you. Order up!

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.

Downtown Chestertown brings smiles by way of doughnuts and pastries made fresh daily for your enjoyment. Everyone has their favorite of course but having a variety of bakeries is what makes downtown so special. Fritters, scones and pies oh my!

Downtown 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.

Why do you love downtown?

Christy Richards
Because I love to shop local and the stores and owners make your visit welcoming inviting you to return again with a smile on their face.

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

Devany
I love downtown because there is so much life all around. From the shoppers walking the streets to the workers stocking the stores. Everybody comes together in one place, different purposes, yet all the same. Downtown stores are always so beautiful. You can see the care workers put into making their store not only clean and beautiful, but also safe and homey.

Valentina Eagar
Fun and unique shopping and eats

Ann Kimball
We are going to be visiting Rockport for our upcoming wedding anniversary!

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:

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.

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.

Call ahead to make sure your reservation is still active and rebook if there are any price drops or changes in number of people staying with you. Another cost saving tips is to bundle the stay with airport parking and shuttle to avoid hefty fees.