Summertime fun in Chestertown, MD on the Eastern Shore

Great Oak Manor is looking forward to a fun filled and memorable Summer season for 2016. Along with all of the wonderful amenities that our property has to offer including kayaks, paddle boards, canoe, hammocks and bicycles the downtown Chestertown district has quite a few events planned. We wanted to highlight some of these upcoming events and hope that you will join us at the Manor as well as take advantage of all that Chestertown has to offer!Fountain








July 22-24, 2016

Chester River Packet will begin it’s weekend ferry service from Chestertown to Rolph’s Wharf

Sat. 23rd – 5k walk /10 mile run beginning in Wilmer Park at 8am, organized by Physically Fitch

Farmers Market in fountain park from 8am – Noon

Dressed ships will rendezvous at Rolph’s Wharf and parade to Chestertown at 2:30 pm, at 4:00 pm Chestertown will officially welcome the Eastport Armada with Fireworks later that evening.

Food, Music and local vendors will be in Wilmer Park until 8 pm

July 29-31, 2016

This is the “Crazy Days” weekend in Chestertown!

Fri. 29th – Crazy Days sidewalk sales begin, there will be music in the evening and shops will be open late

Sat. 30th – Farmer’s Market in fountain park from 8am – Noon

Crazy Days sidewalk sales until 6 pm

Music and kids activities in fountain park Noon – 4 pm

Crab Feast at the foot of High Street beginning at 4 pm!

August 5-7, 2016

Fri 5th – First Friday in Chestertown, Food, Music, Stores and galleries open with samples and festivity

Sat. 6th – Farmer’s Market in fountain park from 8am – Noon

12:30 pm Chesapeake wine trail, wineries will be paired with local businesses

2 pm – 4 pm Winery & Brewery tours and talks

4 pm – 6 pm The Happiest Hour at local restaurants

6 pm – Close Special pairing menus at local restaurants

Sun. 7th – Beer Festival hosted in Wilmer Park beginning at Noon