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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

  • 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

  • Chestertown Challenge Half Marathon Run and 5K Run/Walk [runsignup.com]

    Sun, Oct 11, 2026 at 9:00 AM

    Description

    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...

    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

    18.9 km
    Chestertown, Maryland, 21620, United States
    OpenStreetMap Google Maps

    3.1 Miles 5k 13.1 Miles Half Marathon Run Walk

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