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7 walking events in Sussex County, Delaware

From big races to Saturday morning group runs—find walking events and connect with the local endurance sports community.

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Sussex County

7 events in Sussex County
  • Sun, Mar 08, 2026 at 11:00 AM

    THE HISTORY

    Our story begins in 2008. Irish Eyes had been operating in Milton for almost 2 years and was searching for a way to be more involved with this wonderful town. The Milton St. Patrick's Day Parade was born from this desire to give back to the town that welcomed us with open arms. We had a bit of a slow start....the first year we had only a dozen entries. We raised about $1000 for the Milton Fire Department and Casa San Francisco.

    Now here we are twelve years later and boy have we grown! This year we have three benefactors: The Milton Fire Department, The Milton Chamber of Commerce, the Women's Club of Milton. The 14th Annual Milton St. Patrick’s Day Parade included over 75 entries and combined with the 12th Annual Lucky Leprechaun 5K we were able to donate almost $20,000 to our benefactors. In 2020, the 5k had over 300 participants. In 2021 we were forced to take a year off. In 2022, we had 298 finishers, while in 2023, the event enjoyed the best year to date with a new record of 588 registered participants. We hosted 552 in 2024 and in 2025 a NEW EVENT RECORD OF 661. The key to our success has always been the wonderful support of the local businesses and residents. This year is no different! We know we can count on our community to participate again, so we hope to see you Sunday, March 8th at 11am for the 13th Annual Lucky Leprechaun 5K and at 2pm for the 18th Annual Milton St. Patrick’s Day Parade. Please

    contact Irish Eyes in Milton for more information 302.684.8889. You may also contact us by email at [email protected]

    RACE TIME: 11 am start. Registration opens 9:00 am at Irish Eyes in Milton.

    EARLY PICKUP: Pick up your Race Bib & T-Shirt on Saturday, March 7th from 4 pm - 6 pm at Irish Eyes in Milton and head right to the start on race morning

    RACE LOCATION: Irish Eyes Pub & Restaurant, 105 Union Street, Milton, DE.

    RACE ENTRY FEE: $35 pre registration (through March 7th) $40 day of event.

    TO BENEFIT: Milton Chamber of Commerce, Milton Fire Department & The Women's Club of Milton

    SPONSOR/HOST: Irish Eyes Pub & Restaurant

    RACE COURSE: NEW wheel measured route by the late Doug White. Loop course starting and finishing at Irish Eyes Milton.

    • CLICK HERE

    RACE TIMING: Seashore Strider Event Production will chip time the event using the Chronotrack chip timing system.

    RACE AMENITIES: Long sleeve Race shirts and refreshments, plus beer and bloody mary's for those over age 21.

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

    Note- In 2023 this event moved to 1 division, a 5K run, walk, skip, gallop, stroll…whatever you want to do to support a great charity, but we have one event of a 5K distance. Same goes for 2024 & 2025 & this year in 2026…one event - a 5K run/walk there is not a separate division for walkers, and there will not be awards given out to walkers. I am just trying to be very clear, so I do not have any issues as I’ve had in the past.

    ENTRY INFO: Make checks payable to “Irish Eyes Foundation.”

    RACE DIRECTOR: Tim Bamforth, Seashore Striders/Seashore Strider Event Production, Inc.

    See full details
    5kRunWalk via RunSignup
  • 18970 Holland Glade Rd, Sussex County, Delaware, 19971, United States
    OpenStreetMap Google Maps
    Sun, Apr 19, 2026 at 9:00 AM

    WELCOME TO THE OY VEY 5K RACE INFORMATION

    We invite you to participate in the12th annual Oy Vey 5k. This event will benefit the Proceeds benefit the educational programs at Seaside Jewish Community. Join the Striders at Seaside on Sunday, April 19th at 9 am for a fun & safe 5k. Run or walk in this event for a great cause!.

    NAME: 12th annual Oy Vey 5k Run and (non-competitive) Walk

    RACE TIME: 9 am start

    RACE LOCATION: 18970 Holland Glade Rd, Rehoboth Beach, DE 19971

    TO BENEFIT: Educational Programs at Seaside Jewish Community

    SPONSOR/HOST: Seaside Jewish Community Center

    PRODUCED BY: Seashore Strider Event Production Inc.

    RACE REGISTRATION INFO:

    5k Run... ---> $30 each PRE EARLY BIRD Registration entry fee through April 12th at Midnight

    5k Run... ---> $35 each RACE WEEK Registration entry fee through April 18th at Midnight

    5k Run... ---> $40 each RACE DAY Registration entry fee till 9 am

    Fun 1m Walk... ---> $20 each PRE Registration entry fee through April 12th at Midnight

    Fun 1m Walk... ---> $25 each RACE WEEK Registration entry fee through April 18th at Midnight

    Fun 1m Walk... ---> $30 each RACE DAY Registration entry fee till 9 am

    ** 1m Walk untimed

    If using Universal or Entry Form...Mail entry form/payment to reach us by Tuesday of race-week

    Oy Vey 5k; 9 Gander Lane; Lewes, DE 19958

    Make Checks Payable to: “Seashore Striders”

    PACKET PICKUP:. There will NOT be a traditional packet pickup the day before unless pre-registration is over 200p. Packet Pickup will be on race morning from 7:30a - 8:50a.

    RACE COURSE: Fast & Flat...JB Trail of Cape Henlopen State Park

    • COURSE ETIQUETTE
    • ALL PARTICIPANTS ARE REQUIRED TO RUN ON THE COURSE THAT IS MARKED WITH ARROWS AND CONES.

    • PLEASE STAY ON THE ROAD WHERE IT IS MARKED AND POLICE ARE STATIONED

    • DO NOT RACE ON THE SIDEWALK, RUN THROUGH PRIVATE PROPERTY, OR RUN ON THE OPPOSITE SIDE OF THE ROAD. IN MOST CASES YOU SHOULD BE RACING WITH TRAFFIC. (FOR EXAMPLE, IF THE COURSE IS MARKED WITH ARROWS & CONES SO RUNNERS ARE ON THE RIGHT SIDE OF WILMINGTON AND CHRISTIAN STREETS, THEN NO RUNNER SHOULD BE ON THE LEFT SIDE FACING TRAFFIC). ALSO, WHEN THE RACE IS DIRECTED AROUND A CONE OR CONES, FAILURE TO DO SO COULD RESULT IN CUTTING THE COURSE.

    • FAILURE TO FOLLOW THESE RACE INSTRUCTIONS COULD RESULT IN A DISQUALIFICATION FROM THE EVENT. THANK YOU FOR YOUR COOPERATION IN THIS MATTER. RACE DIRECTOR TIM-SS

    • SEASHORE STRIDER COURSE GUIDELINES: THE FOLLOWING ARE NOT ALLOWED IN A SEASHORE STRIDER EVENT...THANK YOU FOR YOUR COOPERATION FOR THE SAFETY OF ALL PARTICIPANTS...RD TIM-SS

    • BIKES ARE NOT ALLOWED TO BE ON THE COURSE RIDING ALONG/PACING ANY REGISTERED RUNNER

    • BANDITS (NON REGISTERED) RUNNERS ARE NOT ALLOWED TO BE IN THE RACE RUNNING ALONG/PACING ANY REGISTERED RUNNER

    • HEADPHONES/EAR PODS ARE DISCOURAGED WEARING IN BOTH EARS DUE TO SAFETY OF HEARING TRAFFIC

    o THIS IS A TOUGH RULE TO ENFORCE AS 85% OF RUNNERS IN RACES LISTEN TO MUSIC AND THE RRCA RECOGNIZED THAT AND MOVED THE ENFORCEMENT FROM A DISQUALIFICATION TO MAKING IT THE RACE DIRECTORS DECISION. MOST RACE DIRECTORS IN THE COUNTRY EITHER IGNORE THE ISSUE OR TRY TO WORK WITH THE RUNNERS. MY STAND AS A RACE DIRECTOR IS TO ASK YOU TO NOT WEAR THEM AND IF YOU ABSOLUTELY MUST THEN ONLY WEAR THEM IN ONE EAR AND AT A LOW VOLUME LEVEL.

    WATER STOP INFO:. Start & Finish & along course near half-way mark.

    RACE TIMING: Seashore Strider Event Production

    RACE AMENITIES: IN 2026 WE WILL RETURN TO A SHORT SLEEVE TECH T

    PARKING: Plenty of parking at REHOBOTH LL FIELD next door to the JCC on Glade Road.

    AWARDS: Custom awards will be presented to the Overall, Master, and the top three finishers in the following 10 age groups for each event:

    5k...9 & U, 10-13, 14-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+

    ENTRY INFO: Make checks payable to “Seashore Striders” if using the paper race application online at www.seashorestriders.com

    RACE DIRECTOR: Tim Bamforth, Seashore Striders/Seashore Strider Event Production, Inc.

    RACE ORGANIZER: Neil Trugman, JCC

    See full details
  • Sun, Jun 14, 2026 at 10:00 AM

    Like Running or Walking? Love Wine? This race is for you!

    Join us on Sunday, June 14, 2026 at 10:00am for an exciting event that features the amazing scenery and landscape of Salted Vines Vineyard & Winery! Salted Vineyard is located in the back roads of Sussex County Delaware with 26-acres of beautiful property and an extensive wine list that includes a taste for every oenophile. So, whether you are a wine expert looking for something new and different, or a wine novice just entering the wonderful world of wine, we welcome you. With extra swag options for all wine lovers, walkers and runners, this race is a sure thing for a great time! This race is timed and scored by J3 Timing. Results will be posted at www.J3Timing.com.

    Registration Includes:

    • T-shirt: Super Soft Ring Spun Cotton t-shirt included!

    • Wine Glass: Shatterproof, Collapsible, and Portable!

    • Finisher Medal: Doubles as a Wine Stopper!

    • Race Bib: Chip timed 5k run/walk

    • Results Posted Online

    • ...and of course, a pour of wine!

    See full details
    5kRunWalk via RunSignup
  • 36944 Country Club Road, Sussex County, Delaware, 19971, United States
    OpenStreetMap Google Maps
    Sat, Jun 27, 2026 at 7:30 AM

    PACKET PICKUP

    PACKET PICKUP FOR THE JUNGLE JIMS 5K ON SATURDAY WILL BE ON FRIDAY JUNE 26TH AT THE NEW BALANCE STORE FROM 4-6 PM. NEW BALANCE IS LOCATED ON RT ONE ON THE RIGHT SIDE JUST BEFORE THE HAMPTON INN AND RT 24.

    18798 Coastal Highway, Rehoboth Beach, DE. 19958

    PICK UP YOUR PACKET AND THEN HEAD RIGHT TO THE STARTING LINE AT JUNGLE JIMS.

    RACE DIRECTOR TIM-SS

    Join the Seashore Striders for one of the most popular races at the beach- The Jungle Jim's 5k Splash. The 5th event in the popular Seashore Strider Championship Series, this year's Jungle Jim's 5k Splash will be held live on June 27th. The Jungle Jim's 5k Splash is a flat & fast course through the Country Club of Rehoboth Beach on the out & back course with proceeds going to the Children's Beach House of Lewes in honor of the late Derrick Lingo.

    RACE LOCATION

    • Location... Jungle Jim's Water Park, 36944 Country Club Rd; Rehoboth, DE. 19971

    RACE TIME

    • Time...7:30 am

    RACE REGISTRATION:

    $30.00 "Early Bird" Registration...through June 21st at midnight

    $35.00 "Pre" Registration June 22nd through June 26th at midnight

    $40.00 "Last Chance" Race-Day Registration. Registration will open at 6:00 am and will close at 7:15am

    Registration will be done online through runsignup. All participants registered by Monday, June 22nd will be guaranteed a t-shirt, while registrations received after June 22nd are "first come"

    Registration can also be done through the mail by printing out the universal entry form, filling it out, including payment and mailing to Seashore Striders C/O Jungle Jim's 5k, 9 Gander Lane; Lewes, DE. 19958. Please mail early so that it arrives by Monday, June 16th to secure your shirt.

    2 WAYS TO REGISTER FOR A SEASHORE STRIDER EVENT

    • ONLINE REGISTRATION through RUNSIGNUP here at this site."The easiest & most popular way to register for Seashore Strider events.

    MAIL-IN REGISTRATION...form can be downloaded from seashorestriders.com on the Jungle Jim's 5k race page. Please fill out the form completely & neatly, double checking Age, Gender, Entry Fee Price (some events have different fees) & Event Choice.Mail completed paper registration to:

    o Seashore Striders; 9 Gander Lane, Lewes, DE. 19958

    • Please make sure entry arrives by Monday of Race Week to be guaranteed an event swag

    • Make checks payable to “Seashore Striders” if using the Universal Entry Form

    TO BENEFIT

    • Children's Beach House of Lewes in honor of the late Derrick Lingo.

    SPONSOR/HOST

    • Jungle Jim's & Seashore Strider Event Production, Inc.

    RACE COURSE

    • The 22nd Jungle Jim's 5k Splash begins inside the waterpark and makes it's way to the Country Club Development of Rehoboth Beach for the out & back course. The race finishes just inside the water park with the award ceremony at the start area. Participants will be able to enjoy the lazy river and normally 1 ride that JJ opens up till 9:30am and then the park will be cleared.

    • You can re-enter the waterpark for the daily rate at 10 am

    RACE TIMING

    • Timing will be done by the Seashore Strider Event Production team and will be using the Chronotrack B Chip system.

    RACE AMENITIES

    • Finish line produced by “Seashore Strider Event Production, Inc.,” Post-Race awards ceremony at 9:30am outside the park at the start area, custom printed t's, custom awards and a great post-race celebration at Jungle Jim's.

    AWARDS

    • Awards will be presented to the Overall Male & Female Champions, Overall Male & Female Masters (40+ yrs.), as well as the top three (3) Male & Female finishers in the following 16 age categories:
    • 9 & under, 10-13, 14-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54, 55-59, 60-64, 65-69, 70-74, 75-79, 80+

    If you miss the awards ceremony you may pick up locally in Lewes at 9 Gander Lane, Lewes or if you are out of town, your award will be shipped to you for a cost of $10 to cover postage. We do take Venmo.

    36th CHAMPIONSHIP SERIES INFO

    • There is no extra fee to enter the Championship Series- just the regular entry fee per race...automatically entered

    To QUALIFY for the Championship Series one must do the following 3 items:

      1. Runners must complete one (1) 5 mile race (2 to choose from)
      1. Runners must complete five (5) 5k's (9 to choose from)
      1. Continued in '23...Runners must complete at least one (1) of the following "Strider Be Kind Good Deeds" listed below sometime during the Series...e-mail "Be Kind Good Deed" to [email protected]

    o Volunteer for a Seashore Strider Series Event

    o Make a Donation to the Seashore Strider Youth Cross Country Team

    o Make a Donation to the Event you are taking part in

    o Help out with any "post-race" refreshments, making the event even better

    • The Final series standings is determined by fastest 5 mile race and 5 fastest 5ks. Runners are placed in age group by their age on 1st race entered.
    • Example: If you run as a 39 year old in your first 3 races and then turn 40 for your final three races, then you will be in the 35-39 age group for the championship series.

    • Runners must register using exact same name for each race if they want accurate results compiled.

    • Series Weekly Standings will be posted at www.seashorestriders.com

    • Seashore Strider Statistician Tim Young.

    REFUNDS/DEFERRAL

    • The Seashore Striders have a "No Refund" policy, however we make every possible attempt to please our client with the following options:
      1. Transfer to a future Seashore Strider owned event of equal value before the end of the current year.
      1. Donate your entry fee to the charity associated with the event or to the Seashore Strider Youth Running program.
      1. Transfer/Defer to the following year at the same event.
    • Thank You for your cooperation & understanding as some situations are beyond the control of the Seashore Striders.

    STRIDER RACE POLICIES

    • Are you wondering about the Strider Race Policies? Do you have questions regarding the following:
    • HOW DO I WEAR BY RACE BIB?

    • WHAT ARE THE TIME LIMITS FOR STRIDER RACES?

    • ARE THEY WALKER FRIENDLY?

    • WILL I RECEIVE A REFUND IF I CAN NOT PARTICIPATE IN THE RACE?

    • ARE WINNERS CHOSEN BY CHIP TIME OR GUN TIME?

    • ARE BABY JOGGERS OR STROLLERS ALLOWED DURING THE RACE?

    • ARE PETS, BIKES, SKATEBOARDS, ETC... PERMITTED ON THE COURSE?

    • ARE HEADPHONES (IPOD, EAR BUDS, MPS....) ALLOWED DURING THE RACE?

    • CAN I WEAR SOMEONE ELE'S BIB WHO CAN NOT MAKE THE RACE?

    • WHAT IF WE MISS THE AWARD CEREMONY?

    • DO YOU MAIL AWARDS, RACE PACKETS?

    • If you have any questions regarding the above topics please CLICK HERE to go to the strider race policies

    RACE DIRECTOR

    • Tim Bamforth, Seashore Striders/Seashore Strider Event Production, Inc.

    • For [email protected]

    SEASHORE STRIDER STORE

    • Go Shopping at seashorestriders.com
    See full details
    5k3.11 MilesRunWalk via RunSignup
  • Sun, Sep 27, 2026 at 9:00 AM

    Sussex SuperHero 5K

    September 27th, 2026 – Sunday in Lewes, DE

    Proceeds benefit Kim and Evans Family Foundation

    Learn more at https://events.ticketleap.com/tickets/kimandevansff/sussex-superhero-5k

    5kRunVirtualWalk via RaceRoster
  • Sun, Oct 18, 2026 at 12:45 PM

    Join Seashore Striders and Mariners Bethel for the 23rd Annual Mariners Bethel Trail Run

    Sunday, October 18, 2026 • Camp Barnes • Frankford, Delaware

    Each fall, our community gathers for more than just a race — we gather for a tradition. The Mariners Bethel Trail Run is a day rooted in faith, fellowship, and the simple joy of being together outdoors.

    Held at beautiful Camp Barnes in Frankford, Delaware, this flat and fast course begins and ends on camp grounds and winds through the scenic trails and peaceful roads of the Assawoman Wildlife Refuge. Whether you’re chasing a personal best or simply taking in the beauty around you, this course welcomes every pace and every participant.

    Race Options for Everyone:

    • 10K Trail Run

    • 5K Trail Run

    • 1, 2, or 3 Mile Family Walks

    Kids Color Run

    The Kids Color Run kicks off before the adult races, so be sure to arrive early and get your whole family excited and moving their bodies! This fun and energetic run is a favorite for our youngest participants — and every child receives a medal at the finish line.

    Whether you’re a seasoned runner, a casual walker, or just looking for a meaningful way to spend the day with family and friends, there is truly something for everyone.

    Not a runner? Come anyway. This special day is designed for the entire community — filled with fellowship, music, laughter, and activities for all ages. It’s a chance to slow down, reconnect, and spend a beautiful day together.

    Awards

    Top 3 finishers in each age group will receive medals, making this a fun and competitive day for runners of all ages and experience levels.

    And let’s talk about everyone’s favorite part… the post-race meal.

    After you cross the finish line, you’ll be welcomed by the incredible Mariners Bethel church family serving one of the most beloved traditions of the day. Enjoy a homemade feast featuring soups, tamales, hot dogs, sandwiches, Caesar salad, fresh fruit, and plenty of desserts. It’s warm, generous, and made with so much love — and for many, it’s the best part of the race.

    Gather inside the pavilion or outside along the Assawoman Canal, where you can relax at picnic tables, enjoy live music, and soak in the peaceful surroundings. There is nothing better than sharing a meal, swapping race stories, and celebrating together as a community in such a beautiful setting.

    Why We Run?

    All proceeds from the event benefit the children and youth ministries of Mariners Bethel, making this day more than just a race — it’s an investment in the next generation and the heart of our church.

    Bring your family. Invite your friends. Come run, walk, volunteer, or simply cheer from the sidelines. However you participate, you are part of something meaningful and special.

    For registration details and additional information, please visit:

    https://www.marinersbethel.org

    We can’t wait to welcome you to this cherished community tradition.

    SPONSORSHIP AVAILABLE...Contact Bill at [email protected]

    DATE & SCHEDULE OF EVENTS: October 18, 2026

    11:00-12:45pm: On Site Registration/check-in and T-Shirt Pick Up

    12:45pm: Kiddie Color Run

    1:00pm: Run and walk

    1:00 – 2:30pm: Post Race Celebration & Lunch

    RACE REGISTRATION

    • 6.2m Run...$35.00 "PRE" Registration through 10/17/26 at midnight ($40 race-day)

    • 3.1m Run...$35.00 "PRE" Registration through 10/17/26 at midnight ($40 race-day)

    • 1, 2, or 3 Mile Walk...$25.00 "PRE" Registration through 10/17/26 at midnight ($30 race-day)

    • Kiddie Run (12u)...$10.00 "PRE" Registration through 10/17/26 at midnight ($15.00 race-day)

    NOTE...T-SHIRTS not guaranteed after MONDAY OCT 12th...."FIRST COME"...REGISTER EARLY!

    2 WAYS TO REGISTER FOR THE EVENT

    • ONLINE REGISTRATION through RUNSIGNUP here at this site. The easiest & most popular way to register for Seashore Strider events.

    • MAIL-IN REGISTRATION...form can be downloaded from seashorestriders.com on the Mariners Bethel race page. Please fill out the form completely & neatly, double checking Age, Gender, Entry Fee Price (some events have different fees) & Event Choice. Mail completed registration and checks made payable to "Seashore Striders" to: Seashore Striders; C/O Trail Run, 9 Gander Lane, Lewes, DE. 19958. Mail in forms must be received no later than October 13th to be processed in time for the event.

    PRODUCED BY

    Seashore Strider Event Production, Inc.

    RACECOURSE

    View Courses on the SS Webpage HERE

    RACE TIMING

    Timing will be done by the Seashore Strider Event Production team and will be using the Chronotrack B Chip system.

    RACE AMENITIES

    Finish line produced by “Seashore Strider Event Production, Inc.” Custom T-shirts, awards, Lunch, LIVE BLUEGRASS MUSIC and a day full of fun for the entire family.

    AWARDS

    Awards will be presented to the Overall Male & Female Champions, Overall Male & Female Masters (40+ yrs.), as well as the top three (3) Male & Female finishers in the following 10 year age increment categories: 9 & under (3.1m), 19 & under (6.2m) to 70+ for both events.

    NEW in 2026 - Medals to Top 3 Finishers in each age group

    REFUNDS/DEFERRAL

    The Seashore Striders has a "No Refund" policy, however we make every possible attempt to please our client with the following options: 1. Transfer to a future Seashore Strider owned event of equal value before the end of the current year. 2. Donate your entry fee to the charity associated with the event or to the Seashore Strider Youth Running program. 3. Transfer/Defer to the following year at the same event. Thank You for your cooperation & understanding as some situations are beyond the control of the Seashore Striders.

    RACE DIRECTOR

    Tim Bamforth, Seashore Striders/Seashore Strider Event Production, Inc. [email protected]

    SEASHORE STRIDER STORE

    READY-SET-GOSHOPPING

    See full details
  • 33587 Bald Cypress Lane, Sussex County, Delaware, 19956, United States
    OpenStreetMap Google Maps
    Sat, Nov 14, 2026 at 12:00 PM

    Held at the beautiful Trap Pond State Park, this event takes runners on a scenic and invigorating course along the Bob Trail—a 4.5-mile loop around the 90-acre Trap Pond.

    The route winds through towering hardwood forests, crosses a picturesque dam at Raccoon Pond, and ventures over boardwalk bridges through freshwater swamps. Runners will be treated to breathtaking views of vibrant fall foliage, offering a colorful backdrop and a true taste of Sussex County’s lowland beauty during peak autumn.

    Lace up and run with purpose—your participation helps support the transformative work of Legacy Academy!

    Find out more about Legacy Academy here.

    Find out more about the Bob Trail here.

    See full details
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