Experience the Best Activities and Shopping in Maryland

When you stay with us you get much more than a wonderful place to stay, you get to experience everything the historic Chestertown, MD area has to offer during your Maryland vacation. While we offer numerous amenities and Inn activities, we encourage all of our guests to get out and explore the quaint town. Not only is everyone very friendly and welcoming, but each small business also has something delightful to offer each member of the family. If you are looking for something to do in Chestertown during your stay, we highly recommend checking out these awesome shops, dining, galleries, and more!

1. Mimi’s Closet

Woman shopping in Chestertown, holding shirt

When you shop at this amazing Chestertown boutique store, we guarantee you will find something you absolutely love. Whether you’re looking for a classic day outfit, professional attire, or something a little classier, you will find it at Mimi’s. Some of their featured designers include Nina McLemore and Saint James.

If you find something you love, make sure to mention you are a Great Oak Manor guest and you will receive 10% off your purchase.

  • 307 High St, Chestertown, MD
  • Mon-Sat 10:00 am-5:00 pm, Sun 12:00 pm-4:00 pm

2. Twigs and Teacups

Woman sorting through unique jewelry

If you’re looking to take something memorable home for yourself, family or friends, then Twigs and Teacups has something for you. This unique shop has tons of eclectic and quirky gifts, including kitchenware, clothing, books, toys, and more! This boutique shop has been in business for decades, it has become a staple within the community and is an absolute must for anyone visiting the area.

As a bonus, Great Oak Manor guests can receive 10% off during the whole month of July!

  • 111 S Cross St. Chestertown, MD
  • Mon-Sat 10:00 am-5:00 pm, Sun 12:00 pm-4:00 pm

3. Chester River Wine & Cheese Co.

Wine and cheese platter

If you’re looking for something tasty to bring back to your room, make sure to stop by this local foodie shop. They offer over 90 types of domestic and internal cut-to-order cheese and charcuterie, delicious pasta dishes, locally raised meats, unique Kent County wines and spirits. If you are wanting a break from shopping and exploring the town, you can also order and sip wine by the glass Thursday through Sunday from 12:00-5:00 p.m.

  • 117 S Cross St, Chestertown, MD
  • Tues-Sat 10:00 am-6:00 pm, Sun-Mon- 11:00 am-4:00 pm

4. Houston’s Dockside Emporium

Man looking through clothing rack

This Kent County gem offers a number of traditional and trendy clothing and neat merchandise for men, women, and children. If you are planning your stay for the month of July, pencil in a stop at this wonderful store for their Crazy Days Sidewalk Sale on July 25-27, 2019, details here.

  • 315 High St #101, Chestertown, MD
  • Mon-Sat 9:30am-5:30pm, Sun 11:00am-4:00pm

5. River Arts Gallery

woman looking at wall art at Chestertown art gallery

You don’t have to be an art enthusiast to enjoy River Arts! Throughout the year they have numerous galleries, events, a pottery and clay studio, transformative cinematic experiences, and even a children’s learning center! This art facility offers many things to do in Chestertown. We promise you’ll never get bored!

  • 315 High St #106, Chestertown, MD
  • Tues-Fri 11:00 am-5:30 pm, Sat 10:00 am-5:30 pm, Sun 11:00 am-3:00 pm

6. The BookPlate

senior couple looking at books in a bookstore

Ranked as one of Maryland’s favorite shopping spots in town, book worms will love Book Plate, an independent bookstore nestled in the heart of downtown Chestertown. Outside of paperbacks and hardcovers, visitors can check out imported pottery, merchandise, local art, and rarities.

  • 112 S Cross St, Chestertown, MD
  • Mon-Sat 10:00 am-5:00 pm, Sun 11:00 pm-4:00 pm

So Much More to Explore…

If you are visiting in the warmer months and want to enjoy the great outdoors, you can also check out our list of recommended Chesapeake Bay activities, including wine tours, kayaking, boating, hikes, and anything your adventurous heart desires. In the meantime, we hope you enjoy the best activities and shopping in Maryland.

Happy Chestertown exploring!