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2023 Chestertown Tea Party Distance Classic Races and Run For Radcliffe Creek School


We are excited to announce the return of the Run For Radcliffe 10 Mile/5k event, as a part of the Chestertown Tea Party. Please join us on Saturday, May 27th, 2023, when we take off from Wilmer Park and head out in to the beautiful Kent County Countryside.

Solstice Stomp 5K @ Cascia Vineyards


Join us for the 7th Solstice Stomp 5K at Cascia Vineyards!! Our benefit again this year is Kinera Foundation's Eastern Shore Regional Hub so that they can continue to provide therapies, support services, trainings, workshops and parent to parent support groups for kids with special healthcare needs. Our Kinera friends are angels on earth and we are happy to help them however we can.

Heart of the Chesapeake Bike Tour


In memory of Bob Brannock, a member of the Y since its opening. Not only did he use the facilities to help with his Parkinson's, he also became our "Bob the Builder." There wasn't a room that Bob didn't touch. He continued to work at the Y until his death in July of 2014. Without the Y, Bob wouldn't have been able to follow his doctor's order of just "Keep Moving!" Bob's legacy will continue at the Y.

44th Mike Sterling 10k/5k


Please join us for the 44th Annual Mike Sterling 10k Race / 5k Walk / 10k Ruck to be held in Crisfield, MD during the annual National Hard Crab Derby. The race will begin and end at the Crisfield City Dock at the end of Rt. 413. Runners, walkers, and ruckers will enjoy a fast, flat course that meanders thru the City of Crisfield as well as the neighborhoods and along the waterfront outskirts.

Historic Stevensville Metric Half Marathon


Kent Island Running Group is proud to hold the second Historic Stevensville Metric Half Marathon This is a 13.1 kilometer run, which equals 8.15 miles. This course takes the runners through historic Stevensville and travels along the scenic Cross Island Trail.

Storm Warriors Boardwalk 5k Run/Walk


Come out and support the Ocean City Lifesaving Museum's annual event.

18th Annual Ben Layton 5K Run/Walk


The Ben Layton 5K is organized to help raise money for Ben's Red Swings and the Leukemia and Lymphoma Society, a blood cancer that Ben had.

Gerry Boyle Firecracker Kids Triathlon


Come take part in a Cambridge tradition, the 2023 Firecracker Kids Triathlon will be held on Tuesday, July 4, 2023 at the Robbins Family YMCA.

Kenzie Rose Youth Triathlon


The Kenzie Rose Youth Triathlon is a multisport race geared toward the youngest competitors, ages 5-15 - the future of the sport. This is a USAT-sanctioned race, and will be timed.

Skipjack Run


#irunthisbridge - the elegantly sloping half mile of Deal Island Bridge greets you at the start AND finish of both distances!

#runwithaview - the Chesapeake Bay Skipjack Fleet graces the harbor at the start line. It is the last commercial sail powered fishing fleet in North America and the only cohesive sailing fleet in the western hemisphere.



The 19th Annual Race will be a Hybrid Race meaning there will be 2 ways to "Race your Race"

Run Like The Dickens 5K Run/Walk


Our charming downtown district will offer Victorian-themed food and entertainment to get you into the holiday spirit. Proceeds benefit Main Street Chestertown and the local food pantry.

Godfrey's Farm Blueberry Boogie 5K Run/Walk


Benefits: Benedictine - Learning for Living
Presented by: Godfrey’s Farm

Ocean Games USA


Ocean Games is the ultimate ocean experience for open water swim enthusiasts. Held annually on the third Saturday of July in Ocean City, Maryland, this open water swim challenge consists of a 9-mile and 3-mile swim as well as a two (2) and three (3) person 9-mile relay. Ocean Games is a WOWSA-sanctioned open water swim race.

Believe in Tomorrow 5K


This fun event benefits the critically ill children and their families who Believe In Tomorrow Beach Respite Program serves.

Little Sisters of the Poor NUN RUN 5K and 1 Mile Run/Walk


Our 10th Annual 5K & 1 Mile Fun Run to benefit St. Martin's Home and the Little Sisters of the Poor Baltimore will be held September 16th, 2023.

Chestertown Challenge Half Marathon Run and 5K Run/Walk


Benefits: Kent Association of Riding Therapy, Inc. (KART)

Mikayla's Voice Tri For Inclusion


This is NOT just an event for children with disabilities, but an inclusive race for everyone ~ a race for kids of ALL abilities.

Plus, Mikayla’s Voice Tri for Inclusion is much more than a race. It is a priceless opportunity for all kids and young adults, and an important message for our entire community.

Chesapeake Bay Paddle


The race will benefit Chesapeake Conservancy’s efforts to designate the Chesapeake Bay as a National Park, WaterKeepers Chesapeake to help keep the waters and rivers of the Bay healthy and Oyster Recovery Partnership’s work to plant 10 billion oysters in the Bay.

PanCan Twilight 5k and Sunset Stroll presented by Tidewater Physical Therapy


A new twist on an old favorite, this TWILIGHT run will be held at the Hog Neck Golf Course on Saturday, August 26th. The race will start around sunset (7:30 pm) to ensure that everyone has the full experience. Your course will be lighted by a full moon and by lights on the course. The 5k course will take you from the clubhouse, to the main entrance to the course and on to the cart path to complete your 3.1 mile journey.

ShoreRivers Ride for Clean Rivers


Our 19th year and still going strong!! Come out and support the mission of the ShoreRivers organization. Ride the beautiful back roads of Talbot and Queen Anne’s Counties in support of ShoreRivers’ work for clean waterways.

Rock Hall FallFest Run for Character 5K Run/Walk


Join the Family Fun at the Rock Hall FallFest

Want to see what we are up to in 2022?

TCR Event Management is growing! You can find us primarily on the Eastern Shore of Maryland, but also in Virginia, Delaware, New Jersey, and BEYOND!

You can find a list of all of the races we are associated with by looking at our Partner page on RunSignUp.

We are beyond excited to announce the launch of the TCR Event Management App, available for FREE from Google Play or the Apple Store.​ ALL events, including partner events, will be hosted on the app. All races will have a course map, results, and some selfie filters!! Some races will also feature Live Split Tracking. 


Check it out on both Google Play or the Apple App Store! 

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