Chestertown, MD, summer events bring the town to life. Music in the park. Art on the sidewalks. Fireworks over the Chester River. What better way is there to celebrate this sunshine season?
This historic town on Maryland’s Eastern Shore packs the season with charm and energy. Enjoy weekend festivals, delicious fresh crab, outdoor markets, and waterfront concerts. Walk cobblestone streets and discover something new around every corner. Use our calendar to plan your visit and catch the best of Chestertown this summer.
May 2025 Events
Chestertown Tea Party Festival | May 23-25
The Chestertown Tea Party Festival kicks off the summer with colonial flair and small-town spirit. Held over Memorial Day weekend, this signature event reenacts the 1774 protest against British taxation with actors in full costume.
The weekend features a lively parade, street performers, live music, and local food vendors. Don’t miss watching the rebels tossing tea into the Chester River. It’s a must-see celebration that blends history, community, and fun in the heart of downtown Chestertown.
Sultana Sails | Dates Vary
It all starts with Memorial Day weekend. Sultana Sails raises its sails for the summer season tours. Soak up some sun on the deck of a 1768 schooner. This 2-hour cruise includes a tour of the lower crew quarters—authentic reproductions of years gone by. Activities may vary.
2025 Schedule
- Ticket Cost: $40 / $20 under 12 (members receive 20% discount)
- Sat May 24 | 4:30 – 6:30pm (Chestertown Tea Party)
- Sun May 25 | 11:00am – 1:00pm | 2:00 – 4:00pm (Chestertown Tea Party)
- Sat July 12 | 11:00 – 1:00pm | 2:00 – 4:00pm
- Fri Aug 8 | 5:30 – 7:30pm
- Sat Sept 13 |11:00am – 1:00pm | 2:00 – 4:00pm
- Sat Sept 20 |11:00am – 1:00pm | 2:00 – 4:00pm
June 2025 Events
National Music Festival | June 1-14
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! Follow them on Facebook for the latest news.
Antique Airplane Fly-In | June 21
If the science of flight intrigues you, attend the Antique Airplane Fly-In at the Massey Aerodrome this summer! This Kent County event features over 100 antique and classic aircraft, including biplanes and taildraggers. You’ll love watching them take off and land as you learn all about American aviation.
Bay-to-Bay Jim Gent Memorial Ride | June 22
Love cycling? The annual Bay-to-Bay Jim Gent Memorial Ride is a heart-pumping cycling event that everyone can enjoy. There are five different route options ranging from 26 to 102 miles in length. On this journey, you’ll see plenty of beautiful country scenery!
Music in the Park Concert Series | June – August
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!
July 2025 Events
Fourth of July in Chestertown | July 4
Let the celebrations begin for a star-spangled 4th! Parades and fireworks commemorate this annual celebration of freedom. Enjoy food, fun, family, and end the day with a fantastic fireworks display over Rock Hall Harbor.
Kent County 4-H Fair | July 16-19
This annual Eastern Shore event celebrates and supports the youth in our community. The Kent County Fair focuses on educating the public on agriculture. Activities include the greased pig contest, bull-riding, and livestock raised by the youth involved in 4-H. Come and enjoy delicious BBQ (beef, chicken, and pork), additional food vendors, and live entertainment.
Chestertown “Crazy Days” Sidewalk Sale: July 24-26
Every July, the merchants of downtown Chestertown set up shop on the sidewalks for Crazy Days. They offer deeply discounted prices on their goods to make room for their holiday shipments. Shops of all kinds participate—book, clothing, jewelry, houseware, and unique gift shops.
There’s also plenty of street food to taste and a festive atmosphere to enjoy. The Chestertown Sidewalk Sale only lasts for a few days each summer. You don’t want to miss it!
August 2025 Events
Pirates and Wenches Weekend | August 8-10
The waterfront turns into a pirate haven with costumes, music, and mayhem. The Pirates and Wenches Weekend includes a sea shanty sing-along, rum tastings, and a pirate parade. Boats, buccaneers, and fun take over the town. It’s a weekend of swashbuckling adventure for all ages.
Legacy Day Weekend | August 15-17
Each year, we celebrate the rich cultural African-American heritage of the Eastern Shore. Legacy Day Weekend is filled with exhibits, a parade, receptions, artisan booths, and dancing in the streets. It’s a time to show respect and honor to an important part of our history.
Plan Your Summer Getaway at Brampton 1860
Chestertown, MD, summer events make every weekend an adventure. You’ll enjoy waterfront concerts, colonial reenactments, a dazzling fireworks display, and more. There’s always something happening. But after the music fades and the crowds clear, you’ll want a place to unwind.
We invite you to Brampton 1860, a historic inn just outside town. Enjoy spacious suites, gourmet breakfasts, and beautiful gardens. Sip wine on the porch. Soak in a private tub. Stroll wooded trails or relax in the shade of ancient trees.
Brampton 1860 offers quiet luxury close to action-packed events. It’s the perfect home base for your summer escape. Book your stay today and experience the best of Chestertown in comfort and style.
Ready for a summer vacation you’ll never forget?
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