Check out these places of interest and if you like art, many worthy places to visit are open year round.

 

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

 

April 1 – May 31: Brampton Inn April 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.

April 19: 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.  Please join us to kick off the Cars on High series, which will continue on the third Thursday of each month, 6 to 8 p.m., through October.

April 27 and 28 : Brampton Inn Event Jigsaw Puzzle Contest at Brampton. Wooden puzzles will be provided. Teams of two. Winner gets to keep their puzzle!  Includes lunch on Saturday! Click here to book your stay at Brampton.

May 4: First Friday in Chestertown

May 6: Crow Vineyard and Winery Wine and Chocolate Pairing. Crow wines paired with amazing Nolia Chocolates!12noon to 4pm $12 pp.

May 12: Crow Farm to Table Grill Night 6pm till 9pm $25 pp.

May 17: 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.  Please join us to kick off the Cars on High series, which will continue on the third Thursday of each month, 6 to 8 p.m., through October.

May 20: Washington College’s 235th Commencement (We are fully booked)

May 25 – 27, Memorial Day Weekend: Chestertown, a historic 18th century port, celebrates their colonial resistance.  Chestertown Tea Party Festival.

June 1: First Friday in Chestertown

June 3 – 16: National Music Festival, transforming Chestertown into a hub of music for two weeks every June.

June 9: Crow Farm to Table Grill Night 6pm till 9pm $25 pp.

June 10: start of the “Music in the Park” Summer Concert Series

June 8 to 10: Rock Hall Rock Fish Tounrament

June 21: 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.  Please join us to kick off the Cars on High series, which will continue on the third Thursday of each month, 6 to 8 p.m., through October.

June 23:  Crow Vineyard and Ovation Dinner Theatre present “Till Death Do Us Part”, a comedy/murder mystery. $60 pp.

June 24: Music in the Park” Summer Concert Series

July 4: Independence Day Party at Brampton Inn and watching the Chestertown fireworks from our back yard. Here all events in Kent County.

July 6: First Friday in Chestertown

July 7: Crow Farm to Table Grill Night 6pm till 9pm $25 pp.

July 8: Music in the Park” Summer Concert Series

July 19: 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.  Please join us to kick off the Cars on High series, which will continue on the third Thursday of each month, 6 to 8 p.m., through October.

July 22: Music in the Park” Summer Concert Series

August 3: First Friday in Chestertown

August 5: Music in the Park” Summer Concert Series

August 10 – 12: Pirates and Wenches Fantasy Weekend is a town-wide theme party now in its 11th year. The weekend long, town-wide, theme party features a Sea Shanty Sing A Long, Rum Tasting, Decorated Dinghy Contest, Caribbean Beach Party, Buccaneer’s Ball, 5K Run/Walk, Entertainment and Pirate Performers, Costume Contests, Treasure Hunt and much more!

August 11: Crow Vineyard Walk $30 pp

August 16: 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.  Please join us to kick off the Cars on High series, which will continue on the third Thursday of each month, 6 to 8 p.m., through October.

August 19: Music in the Park” Summer Concert Series

September 7: First Friday in Chestertown

September 8: Chestertown Jazz Festival Stay tuned for the line up. It never disappoints!

September 9: Crow Fest 2018 Live music, vendors, wine, food, tours, grape stomping, games and hayrides. Come and spend the day or just a few hours. VIP Tickets are available and include a special pairing of Crow Wine and food prepared by a celebrity chef!  Get tickets here.

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.  Please join us to kick off the Cars on High series, which will continue on the 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.  Please join us to kick off the Cars on High series, which will continue on the third Thursday of each month, 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 23 – 25: 55th Annual Chestertown Antiques Show

December 7: First Friday in Chestertown