A view from the canal bridge looking down onto the southside of town

Dining & Lodging

Chesapeake City has beautiful waterfront dining, six bars, a brewery, and several bed and breakfasts to accomadate your stay!

Dining & Nightlife Lodging

Dining & Nightlife

Our town has several places to enjoy a delicous meal, including beautiful waterfront dining locations. There are six bars and a brewery for you to check out during your stay! Each dining location is located in town limits and within walking distance.

Front view of the Bayard House at night with lights on the front porch

Bayard House

The Bayard House is located on the south side of town along the canal with a beautiful view of the water. Upstairs you can fine dine or you can check out the ol' Hole in the Wall bar located downstairs.

equipment at Bayheads brew room

Bayheads Brewing Company

Bayheads Brewing Company is Chesapeake City's first and only brewery. You can try one of their many hand crafted ales that are brewed right here in town!

Front view of Cafe on the Bay

Cafe on the Bay

For a cozy atmosphere, a great cup of coffee, and a delicious breakfast sandwich, check out Cafe on the Bay. They also have an affordable lunch menu, ice cream and pastries. There are 2 guest rooms that can be booked on Airbnb.com.

Aieral view of the chesapeake inn and marina

Chesapeake Inn Restaurant & Marina

Order a delicous meal or drink at their outside deck and tiki bar while enjoying a beautiful view. You can also fine dine upstairs.

Outside view of Prime 225

Prime 225

Prime 225 is a fine dining steak house located in downtown Chesapeake City. Their menu includes prime steaks, fresh seafood, and pasta. They also have a full bar.

Outside view of the Rummur Lounge drinking garden

Rummur Lounge

The Rummur Lounge is located inside the Inn at the Canal Bed & Breakfast. They are best known for select rum style drinks.

waterfront view of Schaefer's

Schaefer's Canal House

The only restaurant on the north side of the canal, Schaefer's Canal House has a full bar upstairs with casual dining experience. During warmer months, they open their outside deck with a tiki bar.

The Taproom Dining Area

The Taproom

The taproom is located on the corner of Bohemia Ave and 2nd St. It is a great place to go for dine in crabs and seafood pasta dishes! You can even get all-you-can-eat crabs!

Nearby Dining & Take-Out

Each location is located outside of town limits and may require a vehicle to travel.


Chesapeake City has several Bed & Breakfast locations for you to stay overnight! In addition to the several bed and breakfast locations in town, Chesapeake City has several AirBnB locations! Located approximately three miles out of town is Sinking Springs Retreat, a rustic barn venue with their Tiny House B&B.

Front view of the Blue Max Inn

Blue Max Inn

This historic Inn offers seven luxurious rooms, two suites all with private baths. Scrumptious gourmet breakfasts, four relaxing porches, fireplaces and whirlpool tubs. Walk to waterfront, shopping & dining.

Outside view of the Rummur Lounge drinking garden

Inn at the Canal

Water front and old world romance in this elegant Victorian. Canopy beds, private baths with soaking tubs, gourmet breakfast, wireless internet, water views from most rooms & all porches.

Outside view from the shipwatch Inn

Shipwatch Inn

Waterfront B&B features 8 rooms and 2 suites all with private baths. Luxury amenities include canal-side hot tub, whirlpool baths, full-service breakfast, and breezy vistas overlooking the water for all rooms.