Bikes & Beers Middletown

More cycling events nearby

• Bear Triathlon [rivalraceseries.com] [Register at runsignup.com]

  Sat, May 16, 2026 at 5:00 PM

  Description

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  The Bear Triathlon is a popular early-season race set in the scenic Lums Pond State Park, offering athletes a fast, flat, and beginner-friendly course. Featuring Sprint, Olympic and Youth distance...

  The Bear Triathlon is a popular early-season race set in the scenic Lums Pond State Park, offering athletes a fast, flat, and beginner-friendly course. Featuring Sprint, Olympic and Youth distance options, the event delivers an inclusive and energizing race-day atmosphere for both newcomers and seasoned triathletes. The Bear Triathlon has become a go-to kickoff race for athletes across the Mid-Atlantic and is sanctioned by USA Triathlon.​ ALL information about this event can be viewed at https://www.rivalraceseries.com/beartriathlon.

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  SPRINT TRIATHLON

  750 Meter Swim | 10 Mile Bike | 3 Mile Run

  OLYMPIC TRIATHLON

  1500 Meter Swim| 23 Mile Bike | 6 Mile Run

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  YOUTH TRIATLON

  7-8 yr : Swim 50 yards, Bike 2 miles, Run 0.5 mile

  9-10 yr : Swim 100 yards, Bike 2 miles, Run 0.5 mile

  11-12 yr : Swim 100 yards, Bike 4 miles, Run 1 mile

  13-15 yr : Swim 150 yards, Bike 6 miles, Run 1 mile

  14.1 km from Middletown
  1068 Howell School Rd, New Castle County, Delaware, 19701, United States
  OpenStreetMap Google Maps

  1 Miles 13.6 Miles 29.9 Miles Run Swim Triathlon

• 17th Chesapeake City Canal Race 5k [races2run.com] [Register at raceroster.com]

  Sat, Jun 27, 2026 at 8:00 AM

  Description

  17th Annual Chesapeake City Canal Race 5k

  June 27, 2026 – Saturday

  Chesapeake City, MD

  We ask all participants and guest to bring a non-perishable food item for The Chesapeake City Ecumenical Associations Food Pantry.

  Donations and Proceeds of race go to fund our Recycling Program, Chesapeake City is the Top Recycling Town in Cecil County Fourteen Years running.

  12.6 km from Middletown
  208 Bank Street, Cecil County, Maryland, 21915, United States
  OpenStreetMap Google Maps

  5k Cycling Run

• Lums Pond Triathlon [runsignup.com] [Register at runsignup.com]

  Sun, Aug 02, 2026 at 7:30 AM

  Description

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  Just minutes from I-95 this mid-season Sprint/Olympic race is fast, flat and easy to get to. Staged out of beautiful Lums Pond State Park in Bear, Delaware this is a great race for elite and novice...

  Just minutes from I-95 this mid-season Sprint/Olympic race is fast, flat and easy to get to. Staged out of beautiful Lums Pond State Park in Bear, Delaware this is a great race for elite and novice athletes alike. The freshwater swim starts with a rectangular course that parallels the shore for the first 250 meters. The bike course is super fast and completes a large loop around the park. This course is completely flat, all right hand turns and has great pavement throughout. The run course is amazing with a beautiful, heavily forested mix of single track lake views and wide open graveled walking paths. There are mountain biking, hiking and running trails galore as well as the GoApe ropes course. Or you can relax with friends post race at Stewarts Brewing Company on the way home.

  ***The Lum’s Pond Sprint & Olympic Triathlons are the USA Triathlon Delaware State Championships.

  Qualifying for the Toyota Age Group National Championships. State championships will qualify the top 35% or top five (5) finishers in an age group (whichever is greater). You may only qualify for Olympic-distance Nationals by placing in the Olympic distance State Championship race or Sprint Nationals by placing in the sprint distance State Championship race.

  High School State Championships Exemption: All high school athletes who finish any of the State High School Championships will automatically qualify for Sprint-distance (pending they are at least age 15 as of December 31, 2025)

  Any state championship that occurs after June 1, 2025 will qualify for BOTH 2025 AND 2026 Toyota Age Group Nationals. The qualification criteria for 2025 Age Group Nationals are subject to change from what it is for 2025. Click here to review the full 2023 qualification criteria for Toyota Age Group Nationals.

  Athletes do not have to be a resident of a state to win that state’s championship. Any age group athlete competing in an age group division is eligible to win any state championship.

  This is a beautiful race that you don’t want to miss. Be sure to check out our video HERE, then register below.

  For more details please go to the Kinetic Multisports Lums Pond Triathlon website HERE

  14.1 km from Middletown
  1068 Howell School Rd, New Castle County, Delaware, 19701, United States
  OpenStreetMap Google Maps

  Gravel Mountain Biking Run Swim Trail Triathlon Walk

• Vet Fest [whitehallde.com] [Register at runsignup.com]

  Sat, Sep 26, 2026 at 9:00 AM

  Description

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  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...

  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

  5.5 km from Middletown
  801 Mapleton Ave., Middletown, Delaware, 19709, United States
  OpenStreetMap Google Maps

  1 Miles 5k Cycling Run Virtual Walk

• PHUNT 25K/50K TRAIL RACE [facebook.com] [Register at runsignup.com]

  Sat, Jan 16, 2027 at 8:00 AM

  Description

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  PHUNT 25K & 50K TRAIL RACE

  DISTANCE: 25K & 50K (two loops)

  DATE: Saturday, January 16th, 2027

  WHEN: 50K starts at 8 a.m., 25K starts at 9 a.m. End time is 5 p.m.

  CUT-OFF: AS3 at 4 p.m., which gives...

  PHUNT 25K & 50K TRAIL RACE

  DISTANCE: 25K & 50K (two loops)

  DATE: Saturday, January 16th, 2027

  WHEN: 50K starts at 8 a.m., 25K starts at 9 a.m. End time is 5 p.m.

  CUT-OFF: AS3 at 4 p.m., which gives participants an hour to travel 4 miles to the finish.

  WHERE: Fair Hill Natural Resource Management Area

  START/FINISH: Edward L. Walls Activity Hall.

  The hall is at the intersection of Ranger Skinner Drive & Kennel Road., Elkton, MD 21921. Use 4640 Telegraph Road for navigation apps.

  FEE: Online: $40 + processing fee

  FIELD: Maximum 600 runners, no exceptions.

  AMENITIES:

  All finishers will receive a medal and swag item(buff, beanie, pint glass). The activity hall(start/finish) is heated, w/ full kitchen and restrooms. Capacity is 400, so there will be room to leave your gear, or change of clothes. In addition, alcohol (byob), will be permitted at the activity hall. While ample parking will be available, please consider car-pooling. After all, you’re going to be running around in the woods for at least 4 hours. Wouldn’t it be nice to have a fellow runner to commiserate with on the drive back home?

  There will be a major aid station at mile 4.3, 7.5, and 11.5 over the 15.6 mile course. The start/finish area will also act as an aid station for 50K runners. Aid stations are stocked with a variety of items, such as gels, electrolyte drink, water, soda, beer, candy, cookies, chips, bananas, oranges, broth, bacon, grilled cheese sandwiches, and Uncrustables. Each aid station will have a wood or propane fire pit.

  COURSE: In comparison to other parks in the mid-Atlantic region, Fair Hill is fairly tame. The park has gentle rolling hills, intermingled with moderately steep climbs that will not exceed 150 feet. The 15.6 mile course will start/finish on about 0.5 mile of asphalt/gravel road, which makes it 1.0 miles total. There's about 1.0 miles of pasture/open field running. The remainder is beautiful, single-track trails.

  While not the exact course, this is probably 85% accurate.

  https://www.trailrunproject.com/trail/7013781/phunt-trail-race-course

  WEATHER: It’s the wintertime in the mid-Atlantic; expect anything mother nature has to offer. In fact, in 2014, PHUNT started at a bone chilling 6 degrees before topping out at a blistering 30 degrees. Oh, and runners had to contend w/ 5 inches of fresh snow.

  Having said that, the average low is 24, & the average high is 42.

  REFUNDS, BIB TRANSFERS, & DEFERMENT: Sorry, but we do not offer refunds, bib transfers, or deferment. If you can not make the event, the RD considers your entry fee a donation and the funds will be used as he deems necessary.

  18.2 km from Middletown
  Augustine Herman Highway, Elkton, Maryland, 21921, United States
  OpenStreetMap Google Maps

  25k 50k Gravel Run Trail