Whether you’re chasing a personal best looking for an active weekend away, the calendar of Door County Runs and cycling events offers something for everyone.
With winding shoreline roads, wooded trails, rolling hills and some of the most beautiful state parks in Wisconsin, Door County is practically made for exploring on two feet or two wheels. Throughout the year, runners and cyclists come to the peninsula for everything from casual 5Ks and Thanksgiving fun runs to challenging trail races, half marathons, century rides and a 50-mile ultramarathon.
Whether you’re chasing a personal best or simply looking for a great excuse to plan an active weekend away, the calendar of Door County Runs and cycling events offers something for nearly every ability level.
Here are some of the best Door County Runs, races and cycling events to put on your calendar.
May 1, 2027 | Peninsula State Park
One of the signature Door County Runs of the year, the Door County Half Marathon takes runners through the heart of Peninsula State Park. The USATF-certified half marathon course is entirely paved and winds through the park’s forests, hills and shoreline scenery before finishing near Nicolet Bay.
If 13.1 miles isn’t on your agenda, the event also includes the Nicolet Bay 5K, making this one of the most approachable race weekends for groups with runners of different experience levels.
The location is especially convenient for guests staying in Fish Creek. After crossing the finish line, you can spend the rest of the weekend exploring downtown Fish Creek, grabbing lunch or simply relaxing near the water.
June 12, 2027 | Sturgeon Bay
Trade pavement for trails at the annual Crossroads Trail Run at Crossroads at Big Creek in Sturgeon Bay. The event traditionally includes 10K and 5K trail races along with a shorter 2K fun run.
It’s a great introduction to trail running and another example of what makes Door County runs so unique. Instead of city streets and urban scenery, many local events take advantage of the peninsula’s forests, preserves and natural landscapes.
July 4, 2027 | Fish Creek
Few races are more convenient for guests of Fresh Coast Motel than the annual Hairpin 5K.
Held every Fourth of July in Fish Creek, this popular 5K has become a holiday tradition. The course incorporates one of the area’s most recognizable stretches of road near Peninsula State Park and offers a fun way to kick off Independence Day before enjoying the rest of the festivities around Fish Creek.
If you’re looking for Door County runs that can easily become part of a larger vacation, this is one of our favorites. Run in the morning, then spend the rest of July 4 exploring Fish Creek and enjoying summer in Door County.
September 26, 2026 | Baileys Harbor
Beer and running might not be the most traditional pairing, but that’s exactly what makes the Hey Hey 5K such a fun Door County tradition.
Starting and finishing at Door County Brewing Co. in Baileys Harbor, the 3.1-mile loop takes runners through the back roads surrounding the village before returning to the brewery for a post-race celebration. The event is designed to be approachable and family-friendly, with runners, walkers, strollers and dogs welcome.
Among fall Door County runs, the Hey Hey 5K is an especially good choice for anyone who cares just as much about the post-race festivities as their finish time.
October 10, 2026 | Potawatomi State Park
Fall is one of the most spectacular seasons for running in Door County, and Run Wild puts participants right in the middle of the autumn scenery at Potawatomi State Park near Sturgeon Bay.
Participants can choose between a 5K run/walk and a more challenging 10K, with a Smokey Bear Fun Run available for younger runners. Both the 5K and 10K take place on tree-lined park roads that are closed to traffic during the race.
The event also benefits Friends of Potawatomi State Park, making your miles a way to support one of Door County’s beautiful outdoor spaces.
October 17, 2026 | Sturgeon Bay
Another fall trail-running option arrives just one week after Run Wild. HELP of Door County’s annual trail run offers multiple distances, traditionally including 10K, 5K and 2K options.
October’s cooler temperatures and changing leaves make this one of the most scenic times of year to experience Door County runs, particularly if you prefer wooded trails over paved roads.
October 24, 2026 | Gills Rock to Sturgeon Bay
Ready for something significantly bigger?
The Door County Fall 50 is one of the peninsula’s most iconic endurance events. The course stretches 50 miles from Gills Rock at the northern end of the peninsula to Sturgeon Bay, following Door County’s western shoreline during peak fall-color season.
Participants can tackle all 50 miles as an ultramarathon or divide the distance among a relay team. The combination of distance, scenery and the massive post-race celebration makes the Fall 50 one of the most memorable Door County runs on the annual calendar.
For runners already planning ahead, the following Fall 50 is scheduled for October 23, 2027.
November 7, 2026 | Peninsula State Park
If your idea of a perfect race involves wooded trails, elevation and November temperatures, Pen Park Trails Fest belongs on your list.
Held inside Peninsula State Park, this late-season trail-running celebration features challenging 14K and 30K distances. The courses showcase a completely different side of the park than visitors experience from the main roads, making it an excellent choice for experienced runners looking for something beyond a traditional road race.
The event also supports Friends of Peninsula State Park and local trail development and maintenance.
Best of all for Fresh Coast Motel guests, the race takes place right here in Fish Creek.
November 26, 2026 | Ellison Bay
Start Thanksgiving morning with a few miles outside at the Ellison Bay Gobble Wobble.
Held at Fitzgerald Park, this casual community event is exactly what a Thanksgiving run should be: welcoming, fun and not overly serious. Dogs are welcome, turkey costumes are encouraged and participants gather afterward for a post-run celebration.
If you’re spending Thanksgiving weekend in northern Door County, it’s a great way to get moving before the holiday festivities begin.
November 28, 2026 | Egg Harbor
Why run 26.2 miles when you could run 2.62?
The One Barrel 2.62 Run embraces the fun side of racing with a 2.62-mile course in Egg Harbor on Thanksgiving weekend. The run starts and finishes near the Egg Harbor Marina, followed by a celebration at One Barrel Brewing Company.
Participants receive race swag and a post-run beer, while younger runners can warm up with hot chocolate or cider. It’s one of the most laid-back Door County runs of the year and a fun addition to a Thanksgiving weekend getaway.
Runners aren’t the only endurance athletes who get to experience Door County’s incredible scenery. The peninsula is also home to several major cycling events, with routes that pass orchards, forests, small towns, shoreline overlooks and some of Door County’s most recognizable landmarks.
September 13, 2026 | Sturgeon Bay
Known as “The Big Ride,” the Door County Century is one of the Midwest’s premier recreational cycling events and welcomes thousands of cyclists to the peninsula.
This isn’t a race. Instead, riders can choose their own challenge with 30-, 50-, 70- or 100-mile routes.
Depending on the route, cyclists experience miles of Door County shoreline, orchards, rural roads, parks and communities before returning to Sturgeon Bay. Fully supported rest stops along the way turn the ride into an experience rather than simply a test of endurance.
For serious cyclists, the traditional 100-mile Door County Century is a bucket-list way to see the peninsula.
September 19, 2026 | Sister Bay
Just six days after the Door County Century, cyclists have another opportunity to explore the peninsula during the Peninsula Century Fall Challenge.
Starting and finishing at Sister Bay’s Waterfront Park, riders can choose from 25-, 50-, 62- and 100-mile routes. The courses are designed to highlight northern Door County’s scenic back roads, rural landscapes and waterfront views while avoiding heavily traveled roads whenever possible.
The shorter route makes the event accessible to recreational cyclists, while the metric century and full century offer plenty of climbing and mileage for experienced riders.
A post-ride meal and celebration at Waterfront Park provide a fitting finish to a day on the bike.
The races above are only part of Door County’s active-event calendar. Throughout spring and summer, you’ll also find smaller community races such as the Southern Door Trail Trot, YMCA Blossom Run, Jacksonport Lake to Lake Run, Belgian Days Run/Walk, Washington Island Rec Run and other local events.
That variety is part of what makes Door County runs special. You don’t need to be an ultramarathoner or competitive cyclist to participate. There are events for walkers, kids, families, recreational runners, trail runners, experienced racers and endurance athletes alike.
And when there isn’t an organized race happening, Door County still offers hundreds of miles of roads and trails to explore on your own.
Planning a trip around one of these Door County runs or cycling events? Make Spruce & Shore Motel your home base for race weekend.
Located in Fish Creek, Spruce & Shore Motel puts you close to some of Door County’s best running and cycling terrain while providing an easy jumping-off point for events throughout the peninsula. Peninsula State Park is just minutes away, and downtown Fish Creek’s restaurants, shops and waterfront are right down the road.
For events like the Door County Half Marathon, Hairpin 5K and Pen Park Trails Fest, staying in Fish Creek means you’ll be close to the action and can spend less time driving on race morning.
After crossing the finish line or logging a long day on the bike, head back to Spruce & Shore to relax. Take a dip in our seasonal in-ground pool, unwind around the outdoor propane fire pit under the string lights, or simply kick back and enjoy a slower pace after a day spent exploring Door County.
Whether you’re chasing a PR, running your first 5K, tackling a century ride or cheering on someone you love, Spruce & Shore Motel makes an ideal home base for experiencing the best Door County Runs, rides and outdoor adventures.
Book your stay at Spruce & Shore Motel and turn race weekend into a Door County getaway.
