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11 running, walking, cycling, and other events in Middletown, Delaware

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

11 events
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Middletown

11 events in Middletown
  • Sat, Aug 08, 2026 at 7:00 AM

    Ride beautiful, scenic routes (35, 65 and 100 miles) taking you through flat to gently rolling farmland in central Delaware as the route follows lesser traveled roads from Middletown to Clayton, Hartly, points south, and back. All routes will be marked with route arrows and have Support & Gear (SAG) until 5:00 pm. There are rest stops along the routes at regular intervals, five on the Century route!

    Because of the flat, gently rolling terrain that the route follows, this event has become a “right-of-passage” for many cyclists as they take on the challenge of their “First Century Ride“.

    Event Info/Schedule

    DATE

    Saturday, August 8, 2025

    Rider Check-in: 7:00 am – 9:00 am

    Routes & Support Closure: 5:00 pm

    ADDRESS

    Middletown High School

    120 Silver Lake Road

    Middletown DE 19709

    Parking on the High School parking lot

    CHECK-IN

    Registrants must pass through Rider Check-in to get wristbands for use of rest stops & SAG

    REST STOPS

    Multiple rest stops with food, drink and facilities along routes

    EMAIL

    Holly Maddams, Shorefire Event Director at [email protected]

    Registration

    • Registration is limited to a certain number of participants, so don’t delay in signing up

    • Event registration is ONLY by BikeReg.com online registration

    • Register online at BikeReg

    • Early Registration (until July 15, 2026): $30 per Club member; $45 per non-member

    • Standard Registration (July 16 – August 5, 2026): $40 per Club member; $55 per non-member

    • Late/Event Day Registration (August 6 – August 8, 2026): $50 per Club member; $65 per non-member

    • Event Day Registration is offered for this event

    • Event Day Registration is ONLY by Online Registration

    • Participants on Event Day register via their own cell phones/smart devices

    • Instructions for Event Day Registration are also posted on trailer at event start

    • No cash or credit cards will be accepted at Rider Check-in

    Cue Sheets & GPS Files

    • Cue sheets will be available at Rider Check-in

    • GPS-type Files: On Thursday afternoon prior to the event WCBC will email a link to the GPS files to those who have registered. The route is verified on Thursday to confirm that no adjustments to the route are required. Files will not be issued prior to Thursday afternoon. Please be patient, this step is necessary in our procedure.

    See full details
    CyclingTrail via BikeReg
  • Sat, Aug 15, 2026 at 7:30 AM

    Middletown's longest running 5k. The Peach Festival race signals the original harvest of what was once the largest peach farming area in the Nation. All proceeds benefit the Middletown Athletic Club Scholarship Fund. (read more about the MAC Scholarship here.)

    Please be aware, due to construction work in the park, we have had to move the location for registration and modify the course route.

    Please use caution walking around the park and beware of construction equipment and uneven surfaces.

    See full details
    5kRunWalk via RunSignup
  • Thu, Aug 27, 2026 at 6:30 PM

    O.D.B. DASH 5K

    Powered by The Megan Aitken Team.

    August 27, 2026 – Thursday

    Middletown, DE

    5kRunWalk via RaceRoster
  • Sat, Aug 29, 2026 at 9:00 AM

    The Heron Proud 5k

    Aug. 29th, 2026 - Saturday

    We hope EVERY Heron joins us for an incredible morning of community & fun!

    Sanctioned 5K Race

    Arts & Crafts Mobile Gaming Truck

    Bumper Soccer Yoga Inflatable Obstacle Course

    Delicious brunch for sale by Taco Jardin! Don't forget to bring canned goods for Kids Who Can

    5kKidsRunWalk via RaceRoster
  • Sat, Sep 26, 2026 at 9:00 AM

    Vet Fest 2026

    Run. Ruck. Walk. Ride.

    Vet Fest provides an annual uplifting opportunity for the military and civilian communities to stand together against military and veteran suicide. Focusing on physical fitness, participants are invited to run, ruck, ride, roll or walk their way through their community.

    Honoring the founding location of Vet Fest, Whitehall Delaware will still host the annual event with participants from around the country invited to join in nationally where they are. Virtual runs and rides will take place all weekend long - banning together as a nation to benefit Stop Soldier Suicide’s efforts to reduce the epidemic of military suicide.

    All registrants will be mailed a commemorative Vet Fest 2026 event T-shirt. Register by SEPTEMBER 1st to guarantee your shirt shipment before Vet Fest on September 26th!

    Registration:

    $30 NOW through August 31st

    $35 September 1st - 19th

    $40 September 20th - 27th

    $50 On Race Day

    See full details
  • Sat, Oct 03, 2026 at 8:00 AM

    Register for Delaware's 6th Annual Bike Ride & Beer Festival 2026! BIKES & BEERS Cycling Event Series is at CROOKED HAMMOCK BREWERY for the Best Bike Ride & Beer Event in the business! Ride a 15, 30, or 45-mile route through the beautiful area of Middletown, Delaware followed by a post-ride Beer Festival! Bikes & Beers DELAWARE is the area's premier cycling event departing from CROOKED HAMMOCK BREWERY and traveling the beautiful area of Middletown, DE. All rides feature morning fuel stations, marked routes, GPS turn-by-turn instruction, rest stops, refreshments, ride marshals, and SAG support. Finish back at CROOKED HAMMOCK BREWERY for a beer festival atmosphere of rewarding craft beers, live music, a charity raffle & much more!

    This is a ride for everyone - All riding levels are welcome!

    WHAT IS BIKES & BEERS:

    • Pick your ride distance and create a team of friends & family (optional)

    • Mark your calendar for a fun day of cycling and craft beer!

    • Pre Ride:

    • Check in a half hour before your start time

    • We'll provide parking & further ride info in email instructions

    • Enjoy free coffee & fresh pastries

    • Local bike shops offering last-minute tune-ups

    • The Ride:
    • Ride your distance with ride leaders

    • Fully marked routes & GPS turn-by-turn instructions

    • Mechanical support vehicle

    • Rest stops with snacks & refreshments

    • Post Ride:
    • It's time to enjoy (2) complimentary beers on us!

    • Official co-branded Bikes & Beers Pint Glass for every rider

    • Bikes & Beers high-quality neoprene koozies

    • Enjoy the food trucks, live music, games

    • Check out our Bikes & Beers merch tent & snack stand

    • Live raffle with $3,000+ in prizes!

    • Join & Post your photos on our Facebook Page
    • Keep in touch with your newly made cycling friends!

    *Further event information will be communicated in emails after registration and in the days and weeks leading up to event day!

    WHAT YOU'LL GET:

    • Official Bikes & Beers X CROOKED HAMMOCK 2026 Pint Glass

    • (2) Crooked Hammock Craft Beers are ON US!

    • High-Quality Neoprene Beer Koozies

    • Raffle Ticket with a Chance to WIN PRIZES!

    • Collectable Bike Plate - Event Photos!

    • Unique Pretzels & Athletic Non-Alcoholic Beer

    • Entry into the Post-Ride Party with LIVE MUSIC, RAFFLE, GAMES, FOOD TRUCKS & MORE!

    NEW TO OUR 2026 EVENTS:

    • PROFESSIONAL PHOTOGRAPHERS - At least (3) photographers will be snapping pics of your Bikes & Beers experience during pre-ride, during the ride, and post-ride! We have amazing photo ops!

    • NON-ALCOHOLIC BEER OPTIONS - Still want to ride with us but don't want the alcohol? We now have Athletic Brewing sponsoring all our events! Looks for the blue tent and cooler full of flavorful non-alcoholic brews!

    • COLLECTABLE BIKE PLATES - At check-in, you'll receive a collectible event wristband and bike plate designed just for this event! They look awesome!

    • SPONSOR SNACKS & GIVEAWAYS - Morning coffee, fresh pastries, post-ride pretzel necklaces, recovery protein & much more!

    IT'S A CELEBRATION OF CYCLING AND CRAFT BEER!

    Riders will also receive a free raffle ticket for a chance to win a brand-new bike and a ton of other prizes including a private brewery tour and cycling gear!

    Benefitting local cycling charities to help improve the cycling conditions in your area. Have fun, and give back!

    See full details
  • Sat, Nov 21, 2026 at 9:00 AM

    This run/walk is in memory of Dan Rankin who was tragically hit and killed on Jan 24, 2024 by an impaired driver while out on a run training for a Spartan 50k race.

    Dan was married to his high school sweetheart and they have 4 beautiful children.

    He lived a very full life with no regrets.

    He was an entrepreneur at heart and always ready to lend a helping hand.

    All proceeds will go to Delaware Wrestling Alliance.

    See full details
    5kRunSpartanWalk via RunSignup
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