Loading
Loading
Loading
Loading
Loading
Loading

Things To Do

It's no secret that the Eastern Shore is one of our favorite places. Whether you're looking for beach time, a good bite to eat, or a relaxing stroll through town, there's so much to enjoy while you're here. We've shared some of our favorite spots to help you make the most of the weekend!

Evergrain Bread Company

201 High Street, Chestertown, MD 21620

Madison's favorite place to get coffee!

Lowes Wharf Marina Inn

21651 Lowes Wharf Road, Sherwood, MD 21665

One of Madison and Patrick’s favorite waterfront spots to enjoy with friends! Best experienced by boat, but it’s also accessible by land.

Doc's Riverside Grille

511 Chesterfield Avenue, Centreville, MD 21617

Great spot for lunch or dinner. Yummy food & good drinks. (Fun fact: Madison worked here in high school).

Harris Crab House

433 Kent Narrow Way North, Grasonville, MD 21638

We went here on our first date ❤️ Crabs & orange crushes, best combo ever!

The Sandbar at Rolph's Wharf Marina

1008 Rolphs Wharf Rd, Chestertown, MD 21620

Sunsets, live music, drinks. What more could you ask for?

Chestertown Farmer's Market

High Street, Chestertown, MD 21620

Located on the 200 and 300 blocks of High Street. Every Saturday 8AM - Noon. Madison and May love spending their Saturday mornings here—especially May (she usually scores a treat or two)!

Schrader's Outdoors

16090 Oakland Road, Henderson, MD 21640

One of Patrick's favorite spots to shoot sporting clays. It’s a great way to get outside and enjoy the beautiful Eastern Shore countryside. Make a reservation ahead of time if you plan to go.

Slack Tide Yoga Studio

932 Washington Avenue, Chestertown, MD 21620

For any fellow yogis, Madison is a member at Slack Tide and highly recommends checking it out while you’re in town.

The Retriever Bar

337 1/2 High Street, Chestertown, MD 21620

Madison and Patrick's go-to date night spot! Best. Margaritas. Ever.