Kent County Events Calendar -  This Weekend


  • Rock Hall Cruise Night by Smilin' Jake's
  • Friday, September 19   |  5:30-8:30pm
  • This event runs Sep 19, Rain date Sep 26
  • Location: Main Street, Rock Hall
  • Contact: Jack or Linda
  • Phone: 410-639-7280
  • Email: smilinjakes@gmail.com
  • URL: www.rockhallcruisenightsbysmilinjakes.blogspot.com
  • Display of hot rods, classics, street rods and custom cars. Oldies music til' 8:30. No charge to enter or to view. So, dust off that old ride and come on down.

    Future 2014 date: October 17
  • The Chestertown Book Festival Presents: An Evening with Ryan Grim
  • Friday, September 19   |  7pm
  • Location: Bookplate
  • Contact: Owen Bailey
  • Phone: chesbookfest@gmail.com
  • Email: chesbookfest@gmail.com
  • URL: www.chestertownbookfestival.org/2014-chestertown-b
  • Ryan Grim, Washington Bureau Chief for The Huffington Post and Kent County native, will give a talk on America’s Drug War and the growing shift towards police militarization. Grim is the author of This is Your Country on Drugs, winner of the 2007 Alt-Weekly Award for best long-form news-story for “The Painmaker,” the December 2010 Sidney Hillman Award for “The Poorhouse,” and the 2011 Maggie award for “Behind the Assault on Planned Parenthood.” This event will take place at the Bookplate on Cross Street in Chestertown.
  • schooner SULTANA Public Sail
  • Saturday, September 20   |  11am–2pm
  • Location: The foot of Cannon Street
  • Contact: Liza Brocker
  • Phone: 410-778-5954
  • Email: lbrocker@sultanaeducation.org
  • URL: www.sultanaeducation.org
  • Departing and returning from SULTANA's home port of historic Chestertown (and occasionally other ports around the Chesapeake), SULTANA's two-hour public sails are a great way to sail the Chester River on board a traditional schooner. Passengers are encouraged to help raise the sails, steer using Sultana’s seven-foot long tiller, and explore the authentically reproduced crew’s quarters below-decks.
  • Hidey Hidey Ho!–Sultana Education Foundation's Gala
  • Saturday, September 20   |  6–9pm
  • Location: Clovelly Farm, Chestertown
  • Contact: Liza Brocker
  • Phone: 410-778-5954
  • Email: lbrocker@sultanaeducation.org
  • URL: www.sultanaeducation.org
  • Join Sultana in welcoming The World Famous Cab Calloway Orchestra to the Eastern Shore. The evening will feature great food, friends, lots of dancing and exciting auction items. Proceeds benefit the Sultana Education Foundation.
  • Waterfront Festival
  • Saturday, September 20   |  Noon-4pm
  • Location: Wilmer Park, Chestertown
  • Contact: Katherine Thornton
  • Phone: 410-810-7162
  • Email: kthornton2@washcoll.edu
  • URL: www.washcoll.edu
  • The Center for Environment & Society announces its 8th annual Waterfront Festival! Part of Fall Family Weekend at Washington College, CES celebrates the Chester River and the Chesapeake Bay with the famous cardboard boat regatta, environmental displays, crafts and games, food, and live music!
  • Scott D. Livie Memorial Blue Crab Grand Master's Lacrosse Tournament
  • Saturday, September 20   |  All day
  • This event runs September 20-21
  • Location: Worton Park
  • Contact: Rick Coffin
  • Phone: 410-778-1948
  • Email: info@KentParksAndRec.org
  • URL: KentParkAndRec.org
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  • Relay For Life
  • Saturday, September 20   |  11am–11pm
  • Location: Kent County High School
  • Contact: Steve Atkinson
  • Phone: 410-708-3653
  • Email: sga@Shoretobefun.com
  • URL: www.Relayforlife.com/KentMD
  • It's going to be a 20th Anniversary celebration for the American Cancer Society Relay for Life, Kent MD.
  • Cliff's School Open House
  • Saturday, September 20   |  1–4pm
  • Location: Rt. 289 S. Quaker Neck Road
  • Contact: Carol Cordes
  • Phone: 410-778-9173
  • Email: cbcordes@verizon.net
  • URL: www.kentcounty.com/cliffs_schoolhouse
  • Cliffs School Museum is open to visitors at no charge the third Saturday each month through October. Located 8.5 miles from Chestertown on Rt. 289 South, this one room school served children of watermen's and farmers' families from 1878 to 1939. Preserved and restored by Port of Chester Questers and Kent Retired Teachers, it is in its original location and configuration. Lessons for grades 1-7 on chalk boards, potbellied stove, schoolbooks and Weekly Readers used during its 136 years. Bring the kids!
  • KidSPOT Creativity Center
  • Saturday, September 20   |  10am–2pm
  • Location: 315 High St, Chestertown
  • Contact: Tambra Trevarrow
  • Phone: 410-778-6300
  • Email: riverarts@verizon.net
  • URL: www.chestertownriverarts.org/kidspot/
  • A dedicated children’s creativity center that will be open for free every Saturday for children of all ages to play, create and explore with painting, photography, music, crafts, writing, building and other forms of creative exploration.
  • Time Stands Still by Donald Margulies
  • Saturday, September 20   |  8pm
  • This event runs September 20 – 21
  • Location: Garfield Center for the Arts
  • Contact: Jeff Woodbridge
  • Phone: 410-810-2060
  • Email: jwoodbridge@garfieldcenter.org
  • URL: www.garfieldcenter.org
  • Hugh Gregory Gallagher Motivational Theatre is partnering with the disAbility Coalition to produce Time Stands Still. 2 showings.
  • Cliffs School Museum open house
  • Saturday, September 20   |  1–4pm
  • Location: Cliff's School House – Chestertown
  • Contact: Carol Cordes
  • Phone: 410-778-9173
  • Email: cbcordes@verizon.net
  • URL:
  • Cliffs School is one of two remaining one-room schoolhouses in Kent County. It was erected in 1878 to serve a watermen's and farming community and was so used until 1939. The building has been preserved in its original configuration and is well equipped with many authentic furnishings and artifacts of the era. Sit in students' desks, page through old school books, and try to answer questions on the chalkboards for grades 1-7. Don't miss this gem. Project of Port of Chester Questers. Located 8.5 miles south of Chestertown on Rt. 289 Quaker Neck Rd
  • Harry Potter Read-a-Thon
  • Saturday, September 20   |  10am
  • Location: Bookplate
  • Contact: Owen Bailey
  • Phone: chesbookfest@gmail.com
  • Email: chesbookfest@gmail.com
  • URL: www.chestertownbookfestival.org/2014-chestertown-b
  • In collaboration with the Chestertown Harry Potter Festival, the Chestertown Book Festival will host the Harry Potter Read-a-Thon at the Chestertown Branch of the Kent County Public Library. Sign up to read, or come out to listen as volunteers and participants begin reading Harry Potter and the Sorcerer’s Stone. To sign up, please send an email to chesbookfest@gmail.com or call The Bookplate at (410) 778-4167. This event is part of the Chestertown Harry Potter Festival (September 26 – 27, 2014)
  • Sue Matthews: Swinging On a Star
  • Saturday, September 20   |  8:00 p.m.
  • Location: The Mainstay, 5753 Main Street, Rock Hall
  • Contact: The Mainstay
  • Phone: 410-639-9133
  • Email:
  • URL: www.mainstayrockhall.org
  • The exquisite vocalist Sue Matthews sings the songs of Jimmy Van Heusen backed by pianist Robert Redd, woodwinds player Scott Silbert, bassist Tommy Cecil and a drummer. Many of Van Heusen’s songs were written for Frank Sinatra and Bing Crosby and include such classics as “It Could Happen To You,” “Here's That Rainy Day,” “Come Dance With Me,” and of course, “Swinging On A Star.” Call for reservations. Admission is $20.
  • Cliffs School Museum
  • Saturday, September 20   |  1:00 pm to 4:00 pm
  • Location: Rt 289 South, Cliffs City, MD
  • Contact: Carol Cordes
  • Phone:
  • Email: cbcordes@verizon.net
  • URL: www.kentcounty.com/cliffs_schoolhouse/index.htm
  • One of two remaining one-room schools in Kent County. Erected in 1878 to serve a watermen's and farming community and was so used until 1939. Preserved in its original configuration with authentic furnishings and artifacts of the era. Lessons of the day on chalkboards for all 7 grades. 8.5 mi south of Chestertown. Donations gratefully accepted. Port of Chester Questers project.
  • Lecture: HEROINES AND HELPMEETS: Women and Politics in the War of 1812.
  • Sunday, September 21   |  4pm
  • Location: The Mainstay, 5753 Main Street, Rock Hall, MD
  • Contact: The Mainstay
  • Phone: 410-639-9133
  • Email:
  • URL: www.mainstayrockhall.org
  • The presenter will be Rachel Walker, Ph.D. candidate, American History, University of Maryland.

    Rachel comes with the highest recommendation from the head of the department at Maryland. He says she is vibrant, charismatic, funny,and "one of the best he has worked with in the program".

    Free, Donations accepted.
  • Lecture: Heroines and Helpmates: Women and Politics in the War of 1812
  • Sunday, September 21   |  4:00 p.m.
  • Location: The Mainstay, 5753 Main Street, Rock Hall
  • Contact: The Mainstay
  • Phone: 410-639-9133
  • Email:
  • URL: www.mainstayrockhall.org
  • Rachel Walker, a PhD candidate at the University of Maryland will speak on the roles of women during the War of 1812 as part of Kent County’s War of 1812 bicentennial commemoration. She studies early American history focusing on transatlantic cultural and intellectual networks of the 18th and 19th centuries, gender, race and ethnicity in early America and the social, cultural, and economic transformations of the early nineteenth century. Admission is free. Donations accepted.