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Date:
Sat, Oct 17, 2026 at 8:00 AM
Location:
2010 Sonny Schulz Blvd
Queen Anne's County, Maryland
21666
United States
OpenStreetMap Google Maps
Links:
runsignup.com
Tags:
12.5 Miles 15.6 Miles 15.9 Miles Duathlon Run Swim Trail Triathlon

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!!

More multisport events nearby

  • Chestertown Tea Party Distance Classic Race and Run for Radcliffe [runforradcliffe.com] [Register at raceroster.com]

    Sat, May 23, 2026 at 8:30 AM

    Description

    The 30th Annual Chestertown Tea Party

    Distance Classic Race & Run for Radcliffe

    Saturday, May 23, 2026

    Radcliffe Creek School is excited to host the 30th Annual Chestertown Tea Party Distance Classic...

    The 30th Annual Chestertown Tea Party

    Distance Classic Race & Run for Radcliffe

    Saturday, May 23, 2026

    Radcliffe Creek School is excited to host the 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe.

    As is tradition, the run will help kick off Chestertown's Annual Tea Party Festival on Saturday, May 23, 2026! Hundreds of runners and walkers are slated to take off from Chestertown's Wilmer Park and trek along a 5K or a 10-mile path throughout the beautiful Kent County countryside.

    As the only K-8 school on Maryland’s Eastern Shore focused on serving students with learning differences, Radcliffe Creek School (RCS) stands out as a critical resource for families across the State of Maryland and beyond, whose children have not found success in traditional learning environments.

    When you participate in the Run for Radcliffe, you help fund scholarships for children with learning differences—such as dyslexia and ADHD—who rely on the research-backed methodologies and customized instruction that RCS provides to thrive in the classroom.

    Registration will remain OPEN until right before the event on May 23rd. You will also be able to register in person on the day of the race (but don't wait until then - secure your spot for less AND a race shirt!)

    In-Person Registration & Race Bib Pick-Up

    Friday, May 22nd, 2026, from 3:00 pm - 6:00 pm

    Radcliffe Creek School (201 Talbot Boulevard, Chestertown, MD 21620)

    Saturday, May 23rd, 2026, beginning at 6:30 am

    Wilmer Park (413 S Cross Street, Chestertown, MD 21620)

    In-person registration & morning of registration costs will be an additional $5 + associated fees.

    17.7 km
    445 South Cross Street, Chestertown, Maryland, 21620, United States
    OpenStreetMap Google Maps

    5k Run Walk

  • 16TH WALK/JOG FOR THE "WELL" OF IT 5K [lifetimewellsinternational.org] [Register at runsignup.com]

    Sun, May 24, 2026 at 8:00 AM

    Description

    This is the 16th Annual Walk for the “WELL” of It, spreading awareness of the world water crisis as we raise funds to supply clean water to rural areas of Africa, specifically the countries of Ghana...

    This is the 16th Annual Walk for the “WELL” of It, spreading awareness of the world water crisis as we raise funds to supply clean water to rural areas of Africa, specifically the countries of Ghana and Tanzania, while promoting physical fitness in our own local community. Join the Seashore Striders and the Walk for the WELL of It committee for this worthy cause.

    Read A Great Article on the cause featuring our own Kenny Wood... CLICK HERE

    Or a video on their work... CLICK HERE

    Additional race information can be found at CLICK HERE

    RACE DATE: Sunday, May 24, 2026

    RACE TIME: 8 am start

    RACE LOCATION: Martin Sutton Memorial Park, 302 W 4th St., Ridgely, MD 21660

    RACE DAY PICKUP: Pick up your Race Bib & T-Shirt from 7: 00 a.m. until 7:45 a.m. at the start on race morning at the pavilion located at the NE corner of the park.

    5K RUN ENTRY FEE:

    $35 "EARLY REGISTRATION" (till May 23rd at midnight)

    $40 "RACE DAY" registration from 7 - 7:45 at the Race Location

    1 MILE WALK ENTRY FEE:

    $25 "EARLY REGISTRATION" (till May 23rd at midnight)

    $30 "RACE DAY" registration from 7 -7:45 at the Race Location

    $25 "SLEEP WALKER" anytime charitable contribution

    RACE COURSE:. A loop 5k course on the small town and country roads of Ridgely, MD

    CLICK HERE to view the course

    RACE TIMING: Seashore Strider Event Production

    RACE AMENITIES: Short Sleeve tech race shirts, medals to age group top 3 finishers and light refreshments & music.

    AWARDS: Overall male and female, Masters, plus top 3 in 10 year age groups 13 under to 70 over.

    ENTRY INFO: Make checks payable to “Lifetime Wells International" if using the Universal Entry Form

    RACE ORGANIZERS: North Caroline High School Student, Emma Hansley, with support from Lifetime Wells International volunteers: Marie Freeman & Sue Simmons.

    RACE DIRECTOR: Tim Bamforth, Seashore Striders/Seashore Strider Event Production, Inc. tim@seashorestrider.com

    16.1 km
    302 W. 4th Street, Caroline County, Maryland, 21660, United States
    OpenStreetMap Google Maps

    1 Miles 5k Run Walk

  • Godfrey's Farm Blueberry Boogie 5K Run/Walk Benefiting Benedictine [runsignup.com]

    Sat, Jun 13, 2026 at 9:00 AM

    Description

    Benefits: Benedictine - Learning for Living

    Presented by: Godfrey’s Farm

    When: Saturday, June 13, 2026, 9 A.M. Rain or Shine. Healthy Kids Run (10 & under) starts at 8:55 A.M.

    Where: Godfrey’s Farm,...

    Benefits: Benedictine - Learning for Living

    Presented by: Godfrey’s Farm

    When: Saturday, June 13, 2026, 9 A.M. Rain or Shine. Healthy Kids Run (10 & under) starts at 8:55 A.M.

    Where: Godfrey’s Farm, 302 Leager Road, Sudlersville, MD – Visit godfreysfarm.com for complete details.

    Registration:

    • $30 plus fees until May 13 (t-shirt order date)

    • $35 plus fees May 14 through June 1 (t-shirt subject to availability)

    • $40 plus fees June 1 through event day. Registration starts 7:30 A.M. (t-shirt subject to availability)

    Packet Pick Up: Godfrey's Farm, Friday June 12 8am - 6pm and Race Day 7:30 AM

    Silent Hero: Can’t make the event but would like to show your support? Register as a Silent Hero. We appreciate your support.

    Awards:

    • 5K run awards:
    • Top 1, 2, and 3 male finishers

    • Top 1, 2, and 3 female finishers

    • Age group awards for the Top 1 male runner & Top 1 female runner in each group: 9 and under, 10-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70 and over

    • 5K walk awards:
    • Top 5 male finishers

    • Top 5 female finishers

    • Ribbons to all Healthy Kids Run participants

    Benefits: Benedictine is one of the most comprehensive providers of services for children and adults with developmental intellectual disabilities and autism. They offer a year-round educational program and 365-day residential program for students ages 5-21. Their students come from throughout Maryland, as well as adjoining states. Benedictine’s adult program provide community living, meaningful day, and employment services on the Eastern Shore and Annapolis. To learn more about the great work they do at Benedictine, please go to their website www.benschool.org.

    Team Signup: Sign up as a team of 5 or more and get a discount on ALL of the registrations. Who can have the largest team?

    Amenities: Quality EVENT SHIRTS to all participants as available. Sign up early to insure you get your preferred t-shirt! Festivities to include music, apple cider donuts, blueberry scones, fresh fruit, coupon for free ice cream or fruit slushie, prize drawings, and much more!

    14.3 km
    302 Leager Road, Queen Anne's County, Maryland, 21668, United States
    OpenStreetMap Google Maps

    3.1 Miles 5k Run Walk

  • Run the Vineyards - Harvest Ridge Winery 5K [gooddayforarun.com] [Register at runsignup.com]

    Sat, Jun 20, 2026 at 9:00 AM

    Description

    Run the Vineyards 8th Annual 5K at Harvest Ridge Winery - a family farm winery nestled in the beautiful Delaware countryside...Harvest Ridge welcomes participants back to the picturesque winery with...

    Run the Vineyards 8th Annual 5K at Harvest Ridge Winery - a family farm winery nestled in the beautiful Delaware countryside...Harvest Ridge welcomes participants back to the picturesque winery with delicious reds, whites, and sweet wines to enjoy at the after-party!

    Runners and walkers of all ages and paces welcome to participate in this awesome 5K course featuring a fun, flat run through this one-of-a-kind property, featuring 2 vineyards, a wooded trail, crownstone marker of the historical Mason-Dixon line, and some country roads!

    More than a Race...Run the Vineyards is a unique running series that strives to provide families and friends a memorable running experience and opportunities to create new traditions.

    Race Features:

    • Professionally Chip-Timed 5K with Instant Results. Race starts at 9 AM.

    • Custom Tech Tee included. Women's, Men's/unisex, Youth sizes. Upgrade to Women's Racerback Tank Top for $5 extra. Men's Tank available for no added fee. *Please Register by June 7 to guarantee first choice. Many extras ordered and available while supplies last after June 7.

    • Complimentary Glass of Wine for all finishers over 21.

    • Run the Vineyards Stemless Wine Glass included

    • Souvenir Finisher Medals available for $8 during registration or $10 on race day (while supplies last)

    • Water stations, friendly course volunteers, Finish Line waters and bananas

    Post-Race Party Features:

    • Awards for Top 3 Male/Female Overall and Age Group Winners (14 & under, 15-19, 20-29, and every 10 yrs)

    • Live Music until Noon

    • Food Tuck on-site for the after-party

    • Lawn games and indoor or outdoor seating

    • Relax on the outside patio overlooking the beautiful vineyards while listening to live music until noon. And stay longer as vineyard is open to guests all day!

    • Free Downloadable Race and After-Party Photos. Professional Photographer on staff.

    • Race is rain or shine. No refunds or deferrals.

    • Packet Pick-Up: Race Day @7:30 - 8:30 AM at the "Good Day for a Run" tent behind the winery.

    Volunteers receive glass of wine and free future race! Visit "Volunteer" tab for details & Sign up!

    Invite Facebook friends on the event page here: facebook.com/events/686687964521792

    16.7 km
    Kent County, Delaware, 19964, United States
    OpenStreetMap Google Maps

    5k Indoor Run Trail Walk

  • C3 Rolling Donuts ride [ridec3.org] [Register at runsignup.com]

    Sat, Sep 26, 2026 at 7:00 AM

    Description

    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...

    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

    17.1 km
    100 Dulin Clark RD, Queen Anne's County, Maryland, 21617, United States
    OpenStreetMap Google Maps

    33 Miles 62 Miles 100 Miles Cycling

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