Showing 175 events within 100 km in the next 90 days. Page 1 of 9.
Did you know that Caroline County, Maryland, boasts 78 miles of unpaved roads? C3's Scratch N Denton Gravel Grinder takes in up to 23.7 miles of glorious gravel and hardpack farm tracks over its full 53.9-mile course. There are up to thirteen separate gravel segments in all to explore! The Scratch N Denton™ Gravel Grinder starts and finishes at the beautiful, brand new Eden Town Brewing Co. in Denton, Maryland. At the finish, the first beer is on us! And so is a gourmet lunch from Caroline's at Eden Town food truck! So, bring your friends, bring your grit, and bring your thirst. Let’s ride gravel and toast the dust afterward. See you in Denton!
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!!
RACE DATE - Saturday, August 22nd, 2026
PACKET PICKUP STARTS AT 6:30 PM AT HOG NECK GOLF COURSE
OPENING CEREMONY STARTS AT 7:30 PM
RUN STARTS AT 8:00 PM
A new twist on an old favorite, this TWILIGHT run will be held at the Hog Neck Golf Course on Saturday, August 22nd. 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.
THE SUNSET STROLL we are offering walkers a chance to take a short (approximately 1.5 mile), non-competitive walk on the course as the sun sets. This is an opportunity to walk in support of someone with pancreatic cancer or in memory of someone who died from this terrible disease.
All participants (runners and walkers) will receive a race t-shirt, race bib with timing chip and a PURPLE glow stick in remembrance of those who have suffered from the effects of Pancreatic Cancer. We encourage everyone to come out in their best purple garb, to stay with this theme.
This race benefits the Mid-Shore Pancreatic Cancer Foundation, Inc. The mission of the Mid-Shore Pancreatic Cancer Foundation is to provide hope and support for people fighting pancreatic cancer in our community. We are working toward a day when pancreatic cancer will move from being a deadly disease to being a chronic disease. Check out their website at http://www.midshorepancan.org/
5K Awards will be:
Top 2 in each age group: OVERALL MALE, OVERALL FEMALE, 19 and Under, 20-29, 30-39, 40-49, 50-59, 60-69, 70 and Over
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
What is with the name?
I thought it would be a cool name for a race in the heat and humidity of late July. It's also because Killens Pond, where the race is held, is part of the Murderkill River. Murderkill comes from the Dutch words of "Moeder" which means "Mother", and "Kille" which is "Creek".
Course
A 3.10-ish mile almost all dirt loop, totally within Killen's Pond State Park. Some roots, rocks (a seashell or so), rubble - but way gentler than most trails, no rainwater and low rise (maybe 80 feet of climb per loop total). Probably a 1/10 on the technical scale. The good news is it will be mostly shaded. Also, if you get too hot, plenty of opportunities to jump in the pond, esp near the boat ramp. Most wear light trail shoes, few wear road running shoes. No need for super technical trail shoes on this course. The only parts that are not trail are the loop around the parking lot that is .28 of a mile and the aluminum footbridge that is probably .2 miles. North portion of Pondside Trail is broad and mostly dirt (sand+organics). Southside portion is single track with some roots. A footbridge is used to cross pond at dam end. All races will start at 8am (ish) at the picnic tables. Loop around the parking lot and proceed on the Connector Trail (.2 miles) by the picnic tables towards the Pondside Nature Trail then turn right onto the Pondside Nature Trail returning on the connector trail to the turnaround at the parking lot. All races will use the “picnic area” There are bathrooms literally 50 yards from the picnic tables in the parking area. Porta-john MAYBE off south portion of trail near the boat ramp area (Sometimes there is one. Sometimes not).Races are self-supported with a community table for sharing any food/drink/aid. Water will be provided. It won’t be cold. But it will be wet.Timing will be manually. I’ll check off your loops and record your finish time.This race is held in "Fat Ass style". No aid guaranteed (except for water). No shirts (except if you paid for one). No medals. No chip timing. You show up, run the distance, and hang out. If you need to be coddled with fully stocked aid stations, plentiful volunteers to help you, etc, this is NOT the run for you. We are decidedly old school in our approach
Park Information
Killen's Pond is about 15 miles south of Dover, DE on U.S. highway 13. It is a beautiful, well maintained park. Every year, we have first timers comment about what a great and beautiful park and trail it is. Turn left (east) on Killen's Pond Road, indicated by brown park sign, to north entrance of park. Continue past water park to first parking lot and picnic tables at far end. Park should open at 0700 (7 am) for us and will close at sunset, around 2015 (8:15PM). The park has no garbage cans; you bring it in, you pack it out.Parking is ample. Unlike Angela Ivory races in January, the “summer season” at Delaware State Parks charges a fee. This fee is included in your entry fee. I will provide you with a ticket/pass when you arrive.We can't thank the park and their staff enough for their continued support of the race and the excellent job they do on the trails.
Entry
Each race is capped at 30 persons. This means 30 for the 50k and 30 the 12 hour option and 30 for the 50 miler. Why? Well, I'm essentially a one-person operation and any more would make it really hard to manage. There is no waitlist. Why? Because I don't feel like managing one.No deferrals or transfers for the same reason above.
Pricing
All races are capped at $40 (Plus Ultrasignup fees). Why $40? It covers your parking, the park permit fees, race insurance, water (yes I have to buy this). plus the cost of opening the park an hour earlier than their usual opening time for you to arrive.Note that any excess funds remaining after the above will be donated to the park, as well. I do not anticipate this amount being very much at all after looking at the numbers.This is a no refund race. No refunds will be given for ANY reason. If you cancel, your funds will be used to pay above and/or donated to the park.
Other
Weather: EXPECT IT TO BE HOT AND HUMID*It is late July, after all.Plenty of picnic tables. Plenty of parking that is literally right next to the course. You can back your car in and crew yourself easily. PLEASE be respectful that we are visitors of this park. The park is open to all and you will see others using the trail, including families and dogs. Unlike the January event, the park will get “crowded”. The waterpark is open, the campgrounds and cabins will be full, etc.Again, it is a "Pack it In, Pack it out" Park. Do NOT litter. If you see trash, pick it up. We will have trashbags at the picnic tables/pavilion.Not much around the park other than farmland, but:For closest hotels, look up either Holiday Inn Express in Harrington, SpringHill Suites in Frederica or hotels in Dover, DE. Harrington/Frederica are a lot closer (10 minute drive in), but Dover has more options (30 minute or so drive in). You could always rent a cabin at Killens Pond or use the campground. Check their website for details, although it might be slim pickings on the cabins in the summer time (Really nice cabins, btw..Bathrooms, heat, a/c, etc).There is a Royal Farms gas/convenience store probably 3 miles from the Park. Google "Royal Farms Felton, DE" for location. There is a BP gas station and convenience store literally 1 mile outside the park, as well This is a rain or shine event. The ONLY exception to this is thunderstorms. In the event of thunderstorms, I WILL pull ALL runners off the course, as you finish your loop. You will NOT be allowed to start another loop if inclement weather is approaching or we are in the midst of. NO EXCEPTIONS. DO NOT DEBATE ME OR ANY PARK OFFICIALS ON THIS. If you disobey this and start another loop, you are violating race rules and will be disqualified. I don’t mess around with runner safety.TIME LIMITS:All races have 12 hour time limits (8pm-ish)
Event's current local time: 4:13 AM ET
Rumble in the Jungle 5k Run/Walk/Fun Run Kids 6 and under
August 23rd, 2026 - Sunday
Raising money for the Polytech Cross Country student athletes!
We can't wait to show off one of Maryland's FLATTEST courses, with our Marathon, Half Marathon and 5k events, we welcome you to beautiful Talbot County! Our marathon and half marathon share the first 10.5 miles of the half marathon course) and a 5k (out and back from the finish line). Be sure to check out all of the options available.
ALL COURSES ARE USATF CERTIFIED COURSES!!!
Have trouble with course maps? Afraid of missing turns? Looking to set your PR with an all-out effort? Have we got the race for you!!!
The Historic Drawbridge Running Festival will take place on Saturday, October 31st, 2026.. The half will navigate from Tilghman Island, straight up Route 33, and to St Michaels, making one of the only true turns of the race in to the Chesapeake Bay Maritime Museum!! That's a 13.1 mile STRAIGHT RUN with little to no elevation or turns!!!
The Full marathon will follow the same course, but turn right on Bozman-Neavitt Rd (MD Route 579) and travel through tiny Bozman, and turn around right before Neavitt, before you turn around and return to St Michaels, rejoining the marathon course around mile 24.
Our 5k event, starting at 830am, will start and finish from the Chesapeake Bay Maritime Museum!!! The course will be 1.55 out and back on the same course as the Full and Half.
RUNNERS WILL BE ALLOWED TO CROSS THE MAT WITHIN THE FIRST 5 MINUTES (8:00:00 TO 8:05:00) TO PROPERLY DISTANCE THEMSELVES. ALL RUNNERS MUST BE ON SITE AT THE START BY 7:45am.
We encourage participants to take advantage of the buses that will be available at the Maritime Museum on race morning to transport you to the start line at the on Tilghman Island, which is where the race starts. This way your vehicle is available for you upon your finish at the entrance to the Maritime Museum. From the start at Tilghman, we will begin as a group, with traffic briefly shut down on the Island, until we can get everyone safely over the FIRST OF TWO DRAWBRIDGES and on to the shoulder of MD Route 33. Aide stations will be located along the course for your hydration and nutrition needs.
A eight (8) hour cutoff, for the marathon and half marathon, will let you move as fast as you like, all the way to an 18 min 30 second pace. Perfect for those recovering from a long season, or just pushing their limits at the end of the year.
Our friends at the marathon distance will get a whopping 8 hours to complete the event!!!
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
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.
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/.
Hornet Hustle Fall Fest 5k
Benefitting DSU student scholarships and Department of WellRec programs and initiatives.
Saturday, October 17th 2026
Bowers Heritage Day 5k Run Walk
October 11th, 2025 - Sunday
Benefiting Bowers Beach Maritime Museum
Join us on Saturday August 9thth for the Annual Running Hot Clayton Fire 5K.
Post race Fiesta back at the station!
Ready for a challenge that will leave you with unforgettable memories? 🏃 Come participate in the Ironman of Maryland in Cambridge, an epic race that promises to push your limits.
Are you ready to experience the ultimate adventure on two wheels? 🚴♂️ The GFNY Maryland Cambridge invites you to explore the enchanting landscapes of Dorchester County in the heart of Maryland! With its two routes of 48 miles and 92 miles, this competition promises you a challenge that meets your expectations. The winding roads and surrounding natural beauty will provide the perfect setting to push your limits and have an unforgettable experience.
Ready to take on a major challenge while exploring the beautiful city of Cambridge🌟? The Cambridge Half Marathon is the perfect opportunity to push your limits! Imagine running through the historic streets of this charming Maryland town, where every stride brings you closer to not only the finish line but also a charitable cause close to your heart ❤️.