We are extremely excited for you to visit Chestertown and celebrate with us.

Chestertown has become like a second home for us!

Founded in 1706, Chestertown is a historic college town along the banks of the Chester River on Maryland's Eastern Shore. The brick sidewalks lined with shops, restaurants and inns welcome visitors to meander and browse. A visit to Chestertown's Historic District to admire the fine colonial residences is a must!

Stroll historic tree-lined streets, and explore the natural beauty of the Chester River.

Here are a few of our favorite things to do in town:

- Grab breakfast at Evergrain Bread Co. The Sun Buns and Everknots are to die for! And don't forget a baguette for your cheese and pâté later in the day!

- Next, stroll through the farmers market on High Street and grab fresh produce and yummy pies. Don't forget the doggie treats! Loki's favorite are the dried cod skins!

- Then, stop by Chester River Wine and Cheese Co. for some wine, cheese, and pâté. You'll find some of the best food items on the Eastern shore here. Say hello to Jenn and John, the store owners!

-For our history nerds and environmentalists, check out the Sultana Education Foundation, The Holt Center, on S. Cross Street. Chestertown is home to the 1768 schooner SULTANA, docked at the town's marina.

- Move down the block and stop by Twigs and Tea Cups on Cross Street where you can pick up fun gifts and a little something from the Eastern shore.

-We often stop by MassoniArt Gallery to see what great local artists are on display. They have two locations, one on High Street and one on S. Cross Street. A perfect Saturday morning activity.

- There are several great eateries in town. Here are some of our preferred options: Watershed Alley, Phat Daddy's BBQ, Modern Stone Age Kitchen and The Kitchen at the Imperial.

- For our guests staying at the Comfort Inn, Luisa's Cucina Italiana and Procolino's Pizza are two great options near the hotel.

- Lastly, you'll need something sweet after your meal, so head to Stam's Lunchenonette for some ice cream!

Click here to learn more about Chestertown!