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.
Middletown
11 events in Middletown-
Sun, Apr 19, 2026 at 9:00 AMSee full details
Join the Friends of Lums Pond at Volunteer Brewing Company Sunday April 19 for a 5K through Middletown.
As Friends of Lums Pond (501c3 nonprofit), we are a passionate group of volunteers working together to preserve and enhance Lums Pond State Park. Our annual Pond Fest, concert for a cause fundraiser is in October at Lums Pond.
The proceeds from this run will go to enhance Lums Pond. Help us fundraise to put an adaptive kayak launch in at Lums Pond so that everyone can enjoy kayaking on the pond.
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Sat, May 09, 2026 at 9:00 AM
Cavs Crusade 5K
May 9th, 2026 - Saturday
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Sun, May 17, 2026 at 3:00 PMSee full details
Who We Are: Healthy Kids Running Series is a five (5) week running program in the spring and fall for kids Pre-K through 8th grade. Each HKRS Series takes place once a week and offers age-appropriate running events including the 50 & 75 yard dashes, the 1/4 mile, the 1/2 mile and the 1 mile run. Kids will earn points for each race they complete based on their finish.
Pricing: The registration fee covers the entire five (5) weeks of the Series which includes race bibs for each week, a runner shirt, a finisher medal and any sponsor giveaways. Registration is non-refundable and non-transferable. Online Early Bird registration increases three weeks prior to the first race event.
Challenger: This Series offers a Challenger Division which is an adaptive 75 yard race for children with disabilities and/or special needs. This allows for parents, siblings, and friends to be on the course with runners to provide support as well as bringing their own supportive devices such as crutches, braces, wheelchairs, etc. to be used by runners.
Single Day Racing: Single day race registration opens one hour prior to the start of each race. The registration fee covers one single race to be run on the day of registration. ALL single day registrations should be completed onsite at the race location. Single day racers will have the option to upgrade to the full series (see tab on the left side of the page for instructions). There is a strict no-refund and no-transfer policy.
Awards: All participants receive a medal on Week 5! Trophies will be awarded to the overall top finishers in each of the divisions listed below (broken out by boys and girls respectively):
Kindergarten & 1st Grade
2nd & 3rd Grade
4th & 5th Grade
6th to 8th Grade
Challenger
Share your running photos with our community! Find us on Facebook @HealthyKidsRunning or Instagram @healthykidsrs!
#GetUpandGo
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Thu, Jun 11, 2026 at 6:00 PMSee full details
Hustle to Support Families!
Funds raised go directly to supporting families when they need it most during a child's medical journey.
Ronald McDonald House Charities of Greater Delaware provides essential services that remove barriers, strengthen families, and promote healing when children need healthcare. Our programs and support services include our 52-bedroom Ronald McDonald House, two Ronald McDonald Family Rooms, and two hospitality cart programs.
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Sat, Aug 08, 2026 at 7:00 AMSee full details
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
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Registration is limited to a certain number of participants, so don’t delay in signing up
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Event registration is ONLY by BikeReg.com online registration
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Register online at BikeReg
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Early Registration (until July 15, 2026): $30 per Club member; $45 per non-member
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Standard Registration (July 16 – August 5, 2026): $40 per Club member; $55 per non-member
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Late/Event Day Registration (August 6 – August 8, 2026): $50 per Club member; $65 per non-member
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Event Day Registration is offered for this event
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Event Day Registration is ONLY by Online Registration
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Participants on Event Day register via their own cell phones/smart devices
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Instructions for Event Day Registration are also posted on trailer at event start
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No cash or credit cards will be accepted at Rider Check-in
Cue Sheets & GPS Files
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Cue sheets will be available at Rider Check-in
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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.
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Sat, Aug 15, 2026 at 7:30 AMSee full details
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.
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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
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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
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Sat, Sep 26, 2026 at 9:00 AMSee full details
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
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Sat, Oct 03, 2026 at 8:00 AMSee full details
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:
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Pick your ride distance and create a team of friends & family (optional)
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Mark your calendar for a fun day of cycling and craft beer!
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Pre Ride:
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Check in a half hour before your start time
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We'll provide parking & further ride info in email instructions
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Enjoy free coffee & fresh pastries
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Local bike shops offering last-minute tune-ups
- The Ride:
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Ride your distance with ride leaders
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Fully marked routes & GPS turn-by-turn instructions
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Mechanical support vehicle
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Rest stops with snacks & refreshments
- Post Ride:
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It's time to enjoy (2) complimentary beers on us!
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Official co-branded Bikes & Beers Pint Glass for every rider
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Bikes & Beers high-quality neoprene koozies
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Enjoy the food trucks, live music, games
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Check out our Bikes & Beers merch tent & snack stand
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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:
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Official Bikes & Beers X CROOKED HAMMOCK 2026 Pint Glass
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(2) Crooked Hammock Craft Beers are ON US!
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High-Quality Neoprene Beer Koozies
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Raffle Ticket with a Chance to WIN PRIZES!
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Collectable Bike Plate - Event Photos!
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Unique Pretzels & Athletic Non-Alcoholic Beer
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Entry into the Post-Ride Party with LIVE MUSIC, RAFFLE, GAMES, FOOD TRUCKS & MORE!
NEW TO OUR 2026 EVENTS:
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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!
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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!
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COLLECTABLE BIKE PLATES - At check-in, you'll receive a collectible event wristband and bike plate designed just for this event! They look awesome!
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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!
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Sat, Nov 21, 2026 at 9:00 AMSee full details
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.