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October Events in Kent County

October 1 @ 12:00 am - October 31 @ 12:00 am

Car Show

October 1 • 2-6 p.m.

High Street, Chestertown

Register your own pride and joy to compete for trophies, or just stroll the street to admire what other auto enthusiasts have brought to display, from custom hotrods to classic and antique beauties. Category prizes and food and beverage offerings contribute to a fun afternoon that welcomes all. Event is free to the public. A modest registration fee is required for each car entered in the show. Hosted by Main Street Chestertown. For information and to register, visit www.chestertowncarshow.com.

Chestertown Challenge Half Marathon & 5K Run/Walk

October 2 • 9 a.m.

Wilmer Park, Chestertown

The Half Marathon & 5K Run/Walk benefits the Kent Association of Riding Therapy, Inc. (KART), providing therapeutic horseback riding and equine activities for the special needs community. Both courses are USAFT certified. This is a TriState Events Ultimate Challenge Series Event. Race day registration will be available. Packet pickup starts at 8 a.m. and races start at 9 a.m. at Wilmer Park. For details, contact 302-674-3213, races4u@trisportsevents.com, and www.trisportsevents.com.

Mid-Atlantic Symphony Quintet

October 5 • 7:30 p.m.

Washington College, Chestertown

The Washington College Concert Series presents the Mid-Atlantic Symphony Quintet, who will perform two beautiful piano quintets from the 19th century. Join them as they perform Piano Quintet No. 1 in A minor, Op. 30 by Louise Farrenc and Piano Quintet in A Major, D. 667 “Trout” by Franz Schubert. To learn more, visit washcoll.edu/concert.

Rock Hall FallFest

October 8 • 10 a.m.-4 p.m.

Main Street, Rock Hall

Rock Hall FallFest, the annual street fair highlighting great food and great music in a fun family setting, returns to this quaint Kent County waterman’s village for its 25th anniversary. The iconic downtown Main Street becomes a pedestrian thoroughfare for visitors to explore the shops, tour the many artisan and craft booths, and sample local delicacies, particularly the long-awaited opening of the oyster season. Two stages provide non-stop music. Youngsters will be entertained at the expansive Kids Kourt, where there will be puppet shows, magic, balloons, games, pony rides, prizes, clowns, and just plain old-fashioned fun. For details, email RHFallFest@ShoreToBeFun.com.

Touch a Truck Ag Fest

October 8 • 10 a.m.-2 p.m.

Kent County Ag Center, 21349 Tolchester Beach Rd, Chestertown

Come out to the Ag Center and explore emergency vehicles, construction and farm equipment, trucks and more. This is a perfect family event. For details, contact kenttouchatruckagfest@gmail.com or visit www.facebook.com/KentTouchATruckAgFest.

Make a Succulent Centerpiece

October 10 • 1:30 p.m.

Sacred Heart Parish Hall, 510 High Street, Chestertown

Jane Ferguson will deliver a presentation on succulents and demonstrate the creation of a mounded succulent centerpiece. Jane’s presentation is the first event in the 2022-2023 Program of All Seasons Garden Club, which meets on the second Monday of September through December and February through June. Meetings begin at 1 p.m. with a business session, followed at 1:30 p.m. presentation and Q&A, which is followed by refreshments. For details, contact 410-778-4830 or fcreegan2@washcoll.edu.

Echo Hill Outdoor School’s 50th Anniversary Celebration

October 15

Red Acres Farm, Worton

Help Echo Hill celebrate 50 years of magical hands-on environmental education with an unforgettable evening of music, dinner and dancing. Proceeds from the event benefit Echo Hill’s transformative Chesapeake environmental programs. For details, contact 410-348-5880 or info@ehos.org.

Duchamp Won’t Die

October 20-22 • 7:30 p.m.

Washington College, Tawes Theater, Chestertown

In the style of the Neo Futurists, the Washington College Department of Theatre and Dance presents a wild, raucous evening of short, smart, funny plays. This is theater that is a fusion of sport, poetry and living-newspaper. It is a work that embraces those unreached or unmoved by conventional theater. Directed by Professor Dale Daigle and Sophia Rooks ’23, the cast promises to do 30 plays in 60 minutes. For more information, email theatredance@washcoll.edu.

Health & Wellness Expo

October 20 • 8 a.m.-1 p.m.

Kent County Family YMCA, 200 Scheeler Road, Chestertown

Join Homeports for its annual Health and Wellness Expo at the new Kent County Family YMCA. Enjoy free health screenings; free refreshments; flu shots; over 60 exhibitors; a printed program; and transportation. Call 443-480-0940 or email karen.homeports@gmail.com for further information.

Organ Series

October 21 • 7:30 p.m.

Emmanuel Church, 101 North Cross Street, Chestertown

The Emmanuel Episcopal Church Organ Series presents Gabriel Bento, organist at Grace United Methodist Church in Wilmington, Delaware. He is a graduate pf the Oberlin and Julliard Conservatories and the Yale Institute of Sacred Music. For tickets, contact 410-778-3477 or gdb20024@gmail.com.

Chester River Crab Chase 5K Walk and Run

October 22 • 9 a.m.

Wilmer Park, Chestertown

Presented by the Chester River Health Foundation, proceeds from this healthy fundraiser will support the complete renovation of the hospital’s protected courtyard in support of our community’s health care heroes and visitors. The courtyard is frequently used to decompress, eat meals, or hold a meeting. Check-in is at 8 a.m. To register, call 410-810-5660 or email mruehrmund@umm.edu.

Chestertown Rotary Soup & Sip

October 22 • Noon-3 p.m.

The Kitchen at the Imperial, 208 High Street, Chestertown

Chestertown Rotary Club presents this crab soup competition and wine tasting. The public serves as the judge. Bring dollar bills to vote at each booth. The cost is $25 and includes a wine glass and raffle ticket. Proceeds this year will benefit Kent County Public Schools. For more information, contact 410-810-2168 or jlwilliams@kentgov.org.

Studio Tour

October 22-23 and 29-30 • 10 a.m.-5 p.m.

Throughout Kent and Queen Anne’s Counties

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. 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. It is recommended that visitors start the tour at the RiverArts Gallery, 315 High Street, Suite 106 where there will be an exhibit of works by the artists on the tour to help decide on must-see venues. Contact 410-778-6300 or info@chestertownriverarts.org for more details.

Halloween Parade

October 29 • 1 p.m.

Departs Dixon Drive, Chestertown

The Chestertown Lions will host the annual Chestertown Halloween Parade beginning at 1 p.m. on October 29, departing from Dixon Drive, continuing down High Street into the downtown area in front of Fountain Park. Floats, bands, show cars and costumed walkers will be vying for awards and prizes for best of show in various categories. Register from 11:30 a.m. to 12:45 p.m. the day of the parade. Rain date is October 30 at 3 p.m. Visit https://chestertownlions.org.


October 1 @ 12:00 am
October 31 @ 12:00 am


Kent County, Maryland
Chestertown, MD 21620 United States + Google Map
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Allison Rogers



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