Downtown Chestertown, Maryland

Hotels

Hotel Tips

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.

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.

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.

Things To Do

Chestertown visitors are always welcome and you will receive exceptional service from local merchant-owners as opposed to staff at the big box retailers. We take the extra time to make sure that you how to make best use of your purchase and that you get exactly what you need.

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!

Chestertown brings musicians together and finding your local musical instrument shop can be a great way to get to try new and used guitars. Be sure to start your search downtown if you are looking to upgrade, trade-in or add to your collection.

Why Do You Love Downtown?

Darcie Maassen
I love Downtown because I love the beautiful historic buildings. It's a very pretty area aesthetically. I also appreciate the great variety of delicious dining within a small area. Favorites include Capers, Pomodori, Paisanos, Bricktowne Brewery, Elements Tapas bar, Porters, Larks and 4 Daughters. They are all within 4-5 blocks!

Michelle Goodrich
Nice Shops

Krista Bailey
fun and fun

Kim Ward
Unique and wonderful shopping.

Dorothy Wilson
Unique shopping-love the atmosphere

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