Upcoming Events at Great Oak Manor and in Kent County:

National Music Festival – June 3-16
Washington College hosts numerous world-class mentors and gifted apprentice musicians. From violin solos to jazz to masterpieces, the upcoming season of the National Music will delight music lovers. 

Rock Hall Yacht Club Annual Regatta – June 16
The Rock Hall Yacht Club hosts the Annual Summer One-Design Regatta inviting all one design sailboat classes to compete in a two day regatta.

Father’s Day – June 17

Cars on High – June 21
Come to the 300 block of High Street in Chestertown on the third Thursday of the month to see classic, exotic, antique and customized cars. 

Chestertown’s “Music in the Park” Summer Series – June 23
Visit Fountain Park in Chestertown to enjoy a free performances by local and regional artists. Concerts highlight all types of music including big band, jazz, bluegrass and rock.

Bay to Bay Bicycle Ride – June 24
33rd Annual Bay to Bay Bicycle Ride. Start at Betterton Fire Hall which is on the Chesapeake Bay and ride to the Delaware Bay and back. The Bay to Bay ride is 102 miles. Routes from 26 – 102 miles are available.

Street Dance – June 29
Head down to Rock Hall, where Main Street will be closed, for a dance party!

Beach Party – June 30
Visit Rock Hall for the annual Memorial Day Weekend Beach party. Enjoy music, a bonfire, games, and a beautiful Rock Hall sunset.

Waterman’s Day – July 1
Join the townspeople of Rock Hall as they honor and celebrate the traditions of the watermen. Locals take part in numerous competitions including an anchor toss and boat docking.

Fireworks – July 3
Visit Rock Hall and enjoy fireworks on the bulkhead.

Fourth of July Parade & Civic Center Event – July 4
Don’t miss Rock Hall’s iconic July 4th Parade, with floats galore and a marching band. Other events include: the Flat Five Race, breakfast at Legion Hall, a talent show, and free country music concert.

Fireworks – July 4
Head to Wilmer Park in Chestertown for the best view of the Fourth of July fireworks over the Chester River.

Chestertown Independents’ Day First Friday – July 6
Join local vendors in Chestertown for a patriotic twist on a monthly tradition: enjoying Chestertown after dark! Visit the gallery exhibits and unique shops, watch special performances, participate in kids’ activities and enjoy a variety of dining options.

Great Oak Landing Fireworks – July 7
Gather on our private beach at dusk to enjoy a beautiful fireworks display over the Chesapeake Bay!

Chestertown’s “Music in the Park” Summer Series – July 7
Visit Fountain Park in Chestertown to enjoy a free performances by local and regional artists. Concerts highlight all types of music including big band, jazz, bluegrass and rock.

2018 Washington College Riverfront Concert: Ultrafaux – July 12
Enjoy original gypsy jazz inspired by Django Reinhard. 

Sultana Public Paddle – July 13
Join naturalists from the Sultana Education Foundations for a kayak paddle through the Upper Easter Shore. Kayaks are provided. 

Cars on High – July 19
See a variety of classic, exotic, antique and customized cars on High Street. Come admire the rides, chat with the owners, listen to music, and enjoy treats from food trucks!

Kent County Fair – July 19-21
A traditional county fair, the Kent County fair features agriculture education and 4-H exhibits, great food, games, great music, a greased pig contest, corn hole tournament, youth turkey calling contest, animal exhibits, and more!

Chestertown’s “Music in the Park” Summer Series – July 21
Visit Fountain Park in Chestertown to enjoy a free performances by local and regional artists. Concerts highlight all types of music including big band, jazz, bluegrass and rock.

2018 Washington College Riverfront Concert: The High and Wides – July 26
The High and Wides play music inspired by days when lines blurred between bluegrass, old-time, country, boogie, blues, rockabilly, and western swing.

Chestertown Sidewalk Sale – July 27-28
Downtown Chestertown will host two crazy days filled with amazing sales and great shopping deals all over town. There will be live music from 5-9 p.m. on Friday, as well.

Chestertown’s “Music in the Park” Summer Series – August 4
Visit Fountain Park in Chestertown to enjoy a free performances by local and regional artists. Concerts highlight all types of music including big band, jazz, bluegrass and rock.

Call now to book your wonderful getaway in Kent County, MD!

Host Your Special Event at Our Manor on the Chesapeake Bay

It’s no doubt that Great Oak Manor is the perfect setting for a panoramic Eastern Shore wedding, but our slice of the Chesapeake is the ideal venue for any event you might be planning. Consider booking a family reunion, hunting party, yoga retreat, murder mystery party, or a dinner party. We even host corporate events as there are plenty of rooms and spaces for meetings. No matter what you’re planning, you’ll want it to be extraordinary, so why not choose a location that will be equally as memorable? Send an email to  for more information.