Rock Hall Events – April 2022

There’s always something exciting happening in Rock Hall. And at Nauti Properties, we’re all about getting out and enjoying the best local spots the Chesapeake has to offer.

Below you’ll find a list of Rock Hall and nearby events loved by locals and visitors alike. Experience the unique communities in and around Rock Hall and everything the Chesapeake has to offer during the month of April.

Grapes to Glass Seminar

April 3; 1-3 pm

Spend an afternoon in the vineyard with a guided presentation of the techniques for premium grape growing on the Eastern Shore. Then explore winemaking techniques at the winery. Reservations and proof of vaccination are required.

Trustees of the Earth Artshow, Artist Talk

April 7; 5-6:30 pm

In celebration of Earth Day, Trustees of the Earth asks artists and art enthusiasts to imagine a utopian world of thriving natural life. Join artists for a conversation about the intersection of nature and art.

Open Mic Night

April 12; 7 pm

Every second Wednesday, join locals and visitors at The Mainstay for an Open Mic night. Open to all musicians, poets, comics, and the general public. 

Cars on High Street

April 21; 6-8 pm

A short drive to Chestertown delights car lovers with a monthly gathering. Every third Thursday, locals and visitors bring their classic, antique, or custom cars downtown to share with other car-heads and the general public. The event is held weather-permitting.

Draw for Sight Bicycle Poker Ride

April 24; 7:30 am-2 pm

Organized by the Chestertown Lions Club, this charity bike tour offers two distance options: 36 or 60 miles of rolling to flat terrain. The route takes in the scenery of the heartland of Maryland’s Chesapeake Bay communities, including farmlands, old country homes, quaint towns, and great country stores. 

KART Klassic Golf Tournament

April 29; 1 pm

The 6th annual KART Klassic Golf Tournament supports Kent Association of Riding Therapy, a non-profit dedicated to providing therapeutic horseback riding to the special needs community. All are welcome for an afternoon of golf, in scramble format, followed by a post-party at the Back Creek Golf Club.

Chesapeake Bay Charter Cruise


Tour the Chesapeake Bay by sailboat. Seven days a week, Blue Crab Charters takes guests on 90-minute tours and a special sunset tour around the historic Chesapeake Bay. Reservations are required with tours happening daily.

Looking for more to do during your stay? Contact Us! We’re here to help you have the vacation of a lifetime. Thanks and don’t forget to Stay Nauti!