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Event Organizer1 event
Chestertown Lions Club
4102154481
Events organized by Chestertown Lions Club
1 event
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Sat, Jun 27, 2026See full details
The Chestertown Lions Club welcomes cyclists to our annual Bay to Bay Ride; this bicycling challenge offers four tours between 26 and 102 miles.
The 50, 85, or 102 mile flat loop rides take in the scenery of the heartland of the Upper Eastern Shore of Maryland and Deleware including farmlands, old country homes, quaint towns and great country stores.
For those who want a less challenging ride - the 26 mile ride goes through Historic Chestertown. Spend the day touring the town then return to join your friends at the beach. Temperatures in late June lend themselves to a pleasant swim in the Chesapeake Bay at the end of the ride.
Fee includes map, marked route, SAG wagon and five food stops.
Event details and schedule
Registration Hours 0630 am until 0900 am
Ride starts at 0700 am - begins & ends from the Betterton Volunteer Fire Department
Volunteers will direct you to parking upon arrival.
Cycling events nearby
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Distance: 21.4 km from ChestertownSat, Sep 26, 2026 at 7:00 AMSee full details
September 26th, 2025
Routes Of the Eastern Shore of Maryland with amazing routes, farmlands, water views, and Small Towns
Donut and Coffee Hours from Dunkin Donuts
6am to 8:30am
Donut Mascot: photo opt for all.
Lunch
Pupuseria Kent Island Food Truck
11am to 3pm
3 Taco's of your choice with Vegan and Vetgetarin, chicken, beef.
Century Route Pink Arrows
Start Time 7am
https://ridewithgps.com/routes/52107344
Rest Stops
Pecometh
#1 at Mile 19
Saint Lukes Church
#2 at mile 37
Crumpton Fire House
#3 at mile 58
Pecometh
#4 at mile 85
Century Metric Route Green arrows
Start Time 7:30am
https://ridewithgps.com/routes/51926113
Rest Stops
Pecometh
#1 at mile 19
Saint Lukes Church
#2 at mile 37
Pecometh
#3 at mile 50
33 miler blue arrows
Start Time 8:00am
Rest Stop
Pecometh
#1 at mile 21
https://ridewithgps.com/routes/51926324
SWAG:
Rolling Donut Socks
Beer: Bull Goat Brewery
Band: KG Band
Marked course, SAG support, and rest stops.
SAG number
Supporting
Major Taylor Association
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Distance: 17 km from ChestertownSat, Oct 03, 2026 at 8:00 AMSee full details
The Waterman’s Triathlons are nestled on the Eastern Shore of Maryland in picturesque Rock Hall, MD. Just 18 miles from Baltimore “as the fish swims” (put your bike rack on a boat!), Rock Hall is one of the friendliest, most laid back towns anywhere…and is full of history. George Washington took the Annapolis Ferry to Rock Hall nearly ten times before heading to Philly on horseback to work out America’s Independence! The time trial swim takes place in Rock Hall Harbor on the Chesapeake Bay, protecting athletes from any serious wind or chop. The bike course is a triathlete’s dream with beautiful ribbons of pavement and wide shoulders throughout most of the rural course. The run course is pancake flat and takes athletes through the quaint nautically themed neighborhoods and side roads of Rock Hall, MD.
This race is worth the trip to Maryland’s Eastern Shore. Check out our race videos HERE and see why athletes consistently come back year after year to race. Don’t miss out, register today.
For further race details go to https://kineticmultisports.com/races/watermans/.
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Distance: 16.1 km from ChestertownSat, Oct 10, 2026 at 8:00 AMSee full details
Join the Tom McHugh Art Scholarship 5k
When: Saturday, October 10, 2026, 9:00 a.m. Rain or Shine. FREE Kiddie K Run (10 & under) starts at 8:45 a.m.
Where: Waterman’s Crab House & Dock Bar, 21055 East Sharp Street, Rock Hall, MD 21661.
Registration: $30 until Oct 3rd; $35 after and on event day. Registration starts 8:00 a.m. Questions? Contact [email protected]
Silent Hero: Can't attend but would like to show your support? Register as a silent hero. We appreciate your support!
Awards: Awards to overall male/female and master winners, top 3 male/female runners in 10-year age groups awards and top 5 male/female walk finishers. Ribbons to all Kiddie K finishers. The awards ceremony will be held immediately after last participant finishes.
SWAG: Quality "Tom McHugh Arts Scholarship" tech shirts for all of our registered participants.
Celebrate: FallFest is an annual celebration of family, community, and oysters. Live music, entertainment, vendors, artisans, and food will be offered. Rock Hall is a charming waterfront town on the Chesapeake Bay. More information can be found at www.rockhallfallfest.org or www.RockHallMD.com
Our Mission: The Tom McHugh Arts Scholarship has been created to support a student whose character aligns with the spirit of Tom McHugh, a creative artist, an inspirational storyteller, and a community enthusiast. * Proceeds from the 5K will benefit the Tom McHugh Arts Scholarship Award to be presented to a KCHS graduating senior pursuing studies in an Arts curriculum. A portion of the proceeds will also benefit the Rock Hall Elementary School Arts Program.
The website for the Scholarship Site is https://tommchughscholarship.com/
We will continue our Virtual Option!! Run anywhere you like on October 10th to celebrate with us! If you would like a shirt, please note that you will need to make arrangements with the Race Director to pick it up. Shirts will NOT be mailed.
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Distance: 42 m from ChestertownSun, Oct 11, 2026 at 9:00 AMSee full details
Benefits: Kent Association of Riding Therapy, Inc. (KART)
Registration opens at 8 a.m. - Half Marathon Run & 5K Run/Walk start at 9 a.m.
Registration: Race day registration will be available! Packet pickup starts at 8 a.m. and races start at 9 a.m. at Wilmer Park, Chestertown, Maryland.
Silent Hero Donation: Can't make this event but would like to show your support? Register as a Silent Hero!
Benefactor: Kent Association of Riding Therapy (KART) was founded in 1984 to help children and adults with disabilities enhance their social and developmental growth. KART uses a multi-faceted program involving therapeutic horseback riding, barn management, and caring for the horse.
Packet Pickup: All race packets can be picked up on Sunday morning starting at 8 a.m. Race day registration will also be accepted at this time.
Directions: Wilmer Park is located across the street from address 400 South Cross Street, Chestertown, MD. For directions, use your GPS or MapQuest.
Awards: Unique awards for overall male and female winners in the Half Marathon and 5K Run. Awards presented to the top 2 in 10-year age groups in the Half Marathon and 5K Run. Awards to top 2 male and female finishers in the 5K walk. 5K awards will be presented after the last participant finishes. Half Marathon awards will be presented 3 hours after start.
Course: The event starts and finishes at Wilmer Park. The course has gentle rolling terrain and is run entirely on paved country roads.
Course Records: Half Marathon: Male - Hasan Butler - 1:21:27 - 2014, Female – Meredith Tulio - 1:28:29 - 2018. 5K Run: Male - Jesse Goodyear - 17:50 - 2015, Female – Lisa Victorius - 20:50 - 2017
Amenities: Quality “Chestertown Challenge Half Marathon & 5K Run/Walk” Tech Shirts guaranteed to all participants registered by Monday, September 30th. Food and refreshments at the finish line! Police controlled roads, mile markers and directional arrows on road.
Water stops: Water stops will be located at approximately every two miles on the Half Marathon course, at the turnaround of the 5K, and at the start/finish.
Restrooms: Restrooms will be available at the start/finish and on the Half Marathon course.
Spectators: While you're waiting for your friends or family members to complete the race, enjoy the beautiful historic Chestertown sites on the Chester River. Visit www.kentcounty.com/tourism.
Hotels/Motels/Bed & Breakfast: Visit the following websites for a complete list of hotels/motels and bed & breakfast in the Chestertown and Rock Hall area.,
www.kentcounty.com/lodging/rockhall_lodging.php
Inns & Bed and Breakfast in Chestertown, Maryland
Red Roof Inn & Suites Chestertown - ReservationDesk.com
Comfort Inn & Suites Chestertown - ReservationDesk.com
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Distance: 19 km from ChestertownSat, Oct 17, 2026 at 8:00 AMSee full details
Be a part of a celebration of the parks in beautiful Queen Anne's County, Maryland. Just over the Chesapeake Bay Bridge, on the Eastern Shore of Maryland, this straight forward event will be a great way to end your season!
Come experience the Matapeake Beach area with a 1/2 mile swim in the Chesapeake Bay, a 12 mile out-and-back bike ride along the straight and flat Route 8 (Romancoke Road) corridor, and then it's back out for an out-and-back 3.1 mile run on the South Island Trail. Once you see the views from here, you'll be sure to be back for training!!