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6 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.

  • 13th annual Lucky Leprechaun 5k [seashorestriders.com] [Register at runsignup.com]

    Sun, Mar 08, 2026 at 11:00 AM

    Description

    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...

    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.

    5k Run Walk

    105 Union St., Sussex County, Delaware, 19968, United States
    OpenStreetMap Google Maps
  • 12th Oy Vey 5K Run/Walk and 1m Fun Walk [seashorestriders.com] [Register at runsignup.com]

    Sun, Apr 19, 2026 at 9:00 AM

    Description

    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....

    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

    1 Miles 5k 3.11 Miles Run Trail Walk

    18970 Holland Glade Rd, Sussex County, Delaware, 19971, United States
    OpenStreetMap Google Maps
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