5K races near Chesterton

YMCA Run For The Hills is a 5K and 2K held at Camp Triangle Hills of Crossroads YMCA in Crown Point, Indiana, during Fall Fest. The 5K begins first in the morning, followed by the 2K a few minutes later, ensuring families and shorter-distance runners share the same race setup as the longer event. The course is closed to traffic and winds through the hilly 144-acre camp property, offering a campground atmosphere rather than a road race through town. The 5K includes a broad age-group awards structure, along with Athena and Clydesdale divisions. Timing is managed with bib-based computerized results. Run For The Hills serves as the final event in the Crossroads YMCA Triple Crown Challenge, which also includes the Hub Run and Brickyard Run. Proceeds benefit the YMCA Income-Based Scholarship.

The Duneland Half Marathon and 5K begins and ends at Dogwood Park in Chesterton, Indiana. The half marathon starts first, followed shortly by the 5K Run/Walk. This event is Race #10 in the Race the Region series, with both distances contributing to series points. The half marathon course is certified, but the 5K course is not. The event is designed for runners who prioritize efficient logistics alongside the race itself. Timing mats are placed at the start, and chip timing manages finish results. Live results are available via text or email. Directional signs mark every turn. Participants who finish will receive custom medals and shirts. Awards are presented to overall winners, masters runners, and the top three male and female participants in each age group for both races.

Witches in the Woods is a Halloween night race at the Fairgrounds, featuring a timed 5K run and a non-timed 2K walk that begin in the early evening. The course winds through the trees and along Fairgrounds roads after dark, so participants should bring a flashlight or headlamp. This event is designed for more than just fast runners: strollers are welcome, children under 3 participate for free, and the shorter walk offers an accessible option for families and those prioritizing costumes. The race is part of the Hometown Hocus Pocus Market, and registration includes admission to the market following the run or walk. This portion of the evening includes Sanderson Sisters performances, shopping, live music, food, craft drinks, trick-or-treating, costume contests, hay rides, and a photo challenge with prizes for spotting a witch. The competitive 5K still provides official results, with awards for the top overall finishers and the top three in each age category. The Halloween spirit is further reflected in Best Costume awards and finisher medals for the first 200 registrants.

The Jail Break 5K begins at the Old Jail in St. Augustine, Florida, with participants departing at 8:00 a.m. in Halloween costumes. This themed 5K is presented by Old Town Trolley Tours and INK!, with race proceeds benefiting St. Johns County public school students via INK! programs and classroom resources. The course follows the jail-break concept: runners "escape" the historic Old Jail, cross the Vilano Bridge, and proceed toward the Atlantic Ocean. The event is open to runners of all ages and abilities. The morning concludes with a post-race gathering and a costume contest sponsored by the Ghosts and Gravestones Tour. Packet pickup occurs the day before at the Old Town Welcome Center, and registration can be completed online.

Holiday Hustle is a December run/walk in Dexter, Michigan, centered on holiday lights and cold-night energy. The main event is a 5K through neighborhood light displays, with a 1 Mile dash for a shorter option. The series also includes a half marathon and a 13.1-mile relay, allowing walkers, casual runners, relay teams, and longer-distance runners to select a suitable version. The 5K follows Dexter’s decorated neighborhoods, while the half marathon and relay begin and end at Erratic Ale Co., proceeding out-and-back on the B2B Trail through Hudson Mills. The longer races conclude near a fire pit, with an optional cold beer afterward. Entry provides chip timing, finisher medals, official results, awards eligibility by overall and age group placing, and post-race snacks. The event embraces the holiday theme with a “naughty or nice” tone and encourages participants to contribute while burning off holiday calories.

The Portage Township YMCA Turkey Trot is a Thanksgiving Day 5K run/walk starting and finishing at the YMCA on Willowcreek Road. It follows the Rails to Trails route, keeping the race local and straightforward instead of a complicated street course. The event is for YMCA members and the Portage community, welcoming runners and walkers of all fitness levels. A free 1K Kids Fun Run is included for younger children. The race uses computerized chip timing but is not exclusively for fast runners. Families can use the YMCA’s Fun Zone child watch upon registration. Online entrants may receive a long-sleeve wicking shirt, subject to availability and deadlines. Race-day walk-in registration is possible with a late fee. Proceeds benefit the Portage Township YMCA’s Annual Campaign, assisting children and families unable to afford YMCA programs and services. The event has occurred annually for over ten years.

The Thornton Turkey Trot is a Thanksgiving morning run and walk in Glenwood, Illinois. The race hub is located near 183rd Street and Cottage Grove Avenue, adjacent to Sweet Woods Forest Preserve. Established in 1968, it is the oldest turkey trot in Illinois. The primary event is a 5K community run, complemented by a 1-mile community walk and a 1-mile children's race for students in 8th grade and younger. The event is designed for local runners, walkers, school teams, and families, not exclusively for competitive racers. High school teams can compete as a unit if at least three athletes from the same school participate, and the event provides support for student athletes. Runners are also eligible for age-group awards, and all finishers receive medals. This Thanksgiving format links the race to an older American running tradition: the first turkey trot was a YMCA event in Buffalo where six runners completed five miles on unpaved roads.

The Candy Cane Course - Greater Chicago is a Christmas-themed running event held in December at Hammel Woods, starting from the Route 59 Access in Shorewood, Illinois. Families can participate in multiple ways: a Kids Dash, an untimed 1 Mile, chip-timed 5K, 10K, and 15K races, or through virtual participation and a Volunteer then Run option. The 5K, 10K, and 15K include chip timing, live results, awards, a custom bib, a designer shirt, and a finisher medal. The 1 Mile offers the same shirt and medal but without timing. The Kids Dash is for children 10 and under, providing a mini bib, youth shirt, and a crafted medal; children can run this dash for free if they forgo the included items. The event also provides free participant photos, reduced pricing for runners 12 and under in the 5K and 10K, and refreshments at the finish line.

Santa's Boot 5K is a holiday-themed 5K hosted at Off Square Brewing, with the start and finish lines located at the brewery. This is the fifth year for the race, which maintains a straightforward format: a short road race featuring a Santa-themed costume element, welcoming participants of all ages and even pets. The course details are not extensively published, but the out-and-back nature is evident from the brewery's start and finish points. The event attracts individuals seeking to compete, families, and runners accompanied by dogs. Awards are given to the top female and male finishers, along with a distinct prize for the best costume. Each race registration includes entry, a shirt, and a beer or soda post-race.

The Festivus 5K Run is a holiday-themed 5K held at Running Vines Winery in Chesterton, Indiana, on Broadway in the downtown area. Race the Region organizes it as the 12th event in its Race the Region Series, offering a timed 5K for runners and a non-competitive 1K Kids Dash for younger participants. The race employs start-line timing mats and chip timing, meaning each 5K runner’s clock begins when they cross the start line, provided they start within the designated window. Directional signs mark turns, and finish times are dispatched via text or email, with overall results updating online during the event. Participants who finish receive custom medals and certificates. Top overall, masters, and age-group runners contend for custom awards, including miniature Festivus Poles for the leading finishers.

The Santa Run & Walk 5K/2K is a holiday running and walking event in Crown Point, Indiana. The 5K begins at First United Methodist Hall, 352 S. Main, at 8 am, offering a short, straightforward race option in December instead of a long-distance event. The main detail is the dress code: participants are encouraged to wear Santa suits or other holiday attire. Hometown Happenings organizes the event. The 5K distance is suitable for casual runners, walkers, families, and anyone seeking a festive local outing before the holidays.