Fun in the Sun Awaits at the Best Summer Events in Chestertown, Maryland!

What is summer in Maryland to you? Here on the Eastern Shore, it’s a warm breeze rustling through golden grass on the edge of the Chesapeake Bay, the joy of tasting freshly harvested crab, and plenty of festive events! Below, we’ve compiled just a few of our favorite summer events in Chestertown, Maryland. For more local recommendations like these, be sure to access our free Travel Guide to the Eastern Shore of Maryland!

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Some of the Best Summer Events in Chestertown, Maryland

SULTANA Public Sails: Dates Vary

What’s better than soaking up the sun from the deck of a boat? The best way to do just that is aboard the SULTANA! Throughout the summer, this ship offers 2-hour public sails along the Chester River. If you’ve ever wanted to see a real-life, traditional schooner, this is a great way to spend an afternoon. On one of these trips, you may even get to help raise the sails!

Antique Airplane Fly-In: May

If the science of flight intrigues you, attend the Antique Airplane Fly-In at the Massey Aerodrome this summer! This event features over 100 antique and classic aircraft. You’ll love watching them take off and land as you learn all about American aviation.

National Music Festival: June

If there’s one event you shouldn’t miss in Chestertown this summer, it’s the National Music Festival hosted by Washington College! At this exciting event, you’ll enjoy music from all corners of the world. Concerts at this event range from solo recitals to large, orchestral performances. The best part? There are over 200 “open rehearsals” that are free for the public to attend!

Bay-to-Bay Bicycle Ride: June

Love biking? The annual Bay-to-Bay Bicycle Ride is a heart-pumping cycling event that everyone can enjoy. There are five different route options ranging from 27 to 104 miles in length. On this journey, you’ll see plenty of beautiful country scenery!

Music in the Park Concert Series: Dates Vary

Every summer, the Music in the Park Concert Series brings fantastic local tunes to Chestertown’s great outdoors! Held every Saturday in the summer, the Music in the Park Concert Series shows are a perfect way to spend a warm Maryland evening. We can’t wait to enjoy these free shows from our lawn chairs as the gentle river breeze cools us!

Chestertown Sidewalk Sale: July

Every July, the merchants of downtown Chestertown set up shop on the sidewalks and sell their goods at deeply discounted prices (to make room for their holiday shipments). Book, clothing, jewelry, houseware, and gift shops all participate. There’s also plenty of street food to taste and a festive atmosphere to enjoy. The Chestertown Sidewalk Sale only lasts for four days each summer. You don’t want to miss it!

Independence Day Extravaganza Cruise: July

Does an hour-long sail through the Chesapeake Bay complete with hors-d’oeuvres and a fireworks show sound like a perfect way to spend Independence Day? We sure think so! The Rock Hall-based company Blue Crab Chesapeake Sailing Charters offers an incredible Fourth of July trip for up to six people at a time. It’s a fabulous way to view fireworks from the Chesapeake Bay!

Cool Off with Us This Summer at Brampton Inn!Brampton Inn bathtub in room; Summer Events in Chestertown, Maryland

Bring your summer visit to Chestertown full-circle by staying in a family-owned, historic inn that’s operated with love! Brampton Inn is a perfect place for you to cool off with loved ones this summer. Get a good night’s sleep in one of our bright, airy, and spacious accommodations and start the day right with a delicious, freshly prepared breakfast! Later, join us for tea time and social hour for light snacks and refreshing, cold drinks! Finally, end your day “porch surfing” (we’ll explain) as the sun sets over the horizon. Plus, we’re just a short drive away from some of the Eastern Shore’s best seafood restaurants, golf courses, and more. You won’t find any of that at a hotel!

Ready for a summer vacation you’ll never forget? Check our availability today! We book up quickly every summer—don’t miss out!