Our area offers many places of interest and a vibrant arts community.  Many worthy places to visit are open year round. Our favorite venues for live entertainment are the Garfield in Chestertown and the Mainstay in Rock Hall. Check often to get their current shows.

Plan ahead! You don’t want to miss these exciting upcoming events in the Chestertown area or at Brampton:

Through October 31: Brampton Inn Special; stay 2 nights any day of the week and receive a Crow Vineyard and Winery pass for a Wine Tasting Flight of 5, Crow Summer Sausage & Cheese Platter and a Winery Tour. Some date restrictions do apply, please check for availability online.

September 14 – 30: Animal Crackers at the Garfield in Chestertown.

September 20: Cars on High.  Do you have a showstopper of a vehicle you would like to exhibit? Come on down and show it of o High Street. The Cars on High events will resume this Thursday (weather permitting) in the 300 block of High Street, with special musical guests The High & Wides and two food trucks offering casual fare.  Every third Thursday of each month, 6 to 8 p.m., through October.

October 5: First Friday in Chestertown

October 5 and 6: Harry Potter Festival Wizards and loyal Harry Potter fans will convene in Chestertown, Maryland for the Fourth consecutive Chestertown Harry Potter Festival.

October 6th: Chestertown Historic House Tour 1 to 5 pm. Gorgeous historic homes open the doors to the public. A treat!

October 6, 13, 20 and 27: Chestertown Ghost Walk 6 – 9 pm, that should be fun!

October 13: Rock Hall Fest Come enjoy the fall beauty of Kent County when you attend Rock Hall’s annual Fallfest celebration.

October 18: Cars on High.  Do you have a showstopper of a vehicle you would like to exhibit? Come on down and show it of o High Street. The Cars on High events will resume this Thursday (weather permitting) in the 300 block of High Street, with special musical guests The High & Wides and two food trucks offering casual fare.  6 to 8 p.m. Last one for the year!

October 20 and 21 and October 27 and 28: Taking place over the course of two October weekends, the Chestertown RiverArts Studio Tour includes more than 50 working studios throughout Kent and Queen Anne’s Counties. Guests will be invited to explore creative studio spaces, watch artists at work, talk with them about their craft and purchase works at studio prices. Participation in the tour is free, and because it is self-guided, visitors can enjoy this art immersion at their own pace.

October 26 -28: Sultana Weekend. It all started back in November, 2001, when the newly launched schooner SULTANA and the PRIDE OF BALTIMORE II, took a casual sail together on the Chester River the weekend before both vessels “downrigged” for the winter. The combination of a stiff breeze, the fall colors at their peak, and thousands of waterfowl flying overhead, made it a day few onboard either vessel would soon forget. “We’ll have to do this again next year,” remarked both Captains – and so Downrigging Weekend was born. This a “do not miss” weekend. Hurry up and book.

November 2: First Friday in Chestertown

November 26 – December 14: Christmas High Tea at the Brampton Inn, served Mondays, Wednesdays and Saturdays.

November 30 – December 9: Tiny Tim’s Christmas Carole the Garfield in Chestertown.

November 23 – 25: 55th Annual Chestertown Antiques Show

December 1: Start of Fireplace Season at the Brampton!

December 7: First Friday in Chestertown

December 7 – 9: Main Street Chestertown presents “A Dickens of a Christmas” celebration Friday evening through Sunday morning throughout the historic downtown. As an arts-rich community, Chestertown invites visitors to enjoy a memorable weekend filled with authentically themed holiday fun. The charm of our historic 312-year-old river town will be the backdrop to a lively display of Dickens-era holiday attractions: carriage rides, street theater, live music, food vendors, decorated house tour, and more!

December 31: Annual New Years Party at the Brampton! It’s a lively celebration at 6pm with finger food and bubbly!