25 Outdoor Events You Don’t Want to Miss in 2025

I used to not like planning my outdoor pursuits more than a few weeks in advance because it seemed counter to the freedom and spontaneity I associated with the lifestyle. But as human beings in the 21st century, we have so much on our plates, and finding time to do everything can be hard. With this in mind, Terrain has curated a list of 25 races and events you should add to your calendar now, so you can stay motivated, take advantage of those early bird ticket prices, and make the most of your 2025.

 

Missouri Whitewater Championships
Date: March 21-23
Location: Fredericktown, Mo.
Registration: missouriwhitewater.org/competition/mwc

When the spring rains fall and the St. Francis River runs high, the region’s top whitewater paddlers descend on Millstream Gardens Conservation Area for an epic weekend of racing and fellowship. Compete in the downriver sprint or slalom, with categories from novice to expert, or just sit on the pink granite boulders along the shore and cheer on the splashy action.

 

Southern Illinois Outdoor Summit
Date: March 28
Location: Carbondale, Ill.
Registration: ton.siu.edu/partner-camps/southern-illinois-outdoor-summit.php

Brand new for 2025! Come for the informative sessions aimed at building a vibrant outdoor economy in Southern Illinois but stay for access to the Touch of Nature Outdoor Education Center’s heartpounding amenities — including ziplines, ropes courses, and over 14 miles of hiking, biking, and running trails.

 

Ozark Foothills Endurance Runs
Date: April 5-6
Location: Wildwood, Mo.
Registration: terraintrailrunners.com/ozark-foothills.html

One of the few races to tackle the rocky, rolling trails at Greensfelder County Park, Ozark Foothills returns for a 10th time in 2025. If you want long-range distance options, look no further: The weekend offers runs of 100 miles, 100k, 50 miles, 50k (day or night), marathon, 25k, and 25k ruck (a form of hiking with a weighted pack). We’re exhausted just thinking about it.

 

Robinson Bluff Festival
Date: April 5-6
Location: Cadet, Mo.
Registration: emclimbers.com/rbf2025

At $40 a person, you won’t find a lower-priced multi-sport festival than this. Spend your weekend casually exploring the 150+ climbing routes and boulder problems, or sign up for the on-site competition. Need a change of pace? Hit the six miles of hiking/biking trails or the 18-hole disc golf course. At night, revel in music, drinks, and games, then camp under the stars.

Greater St. Louis Marathon
Date: April 26
Location: St. Louis, Mo.
Registration: gostlouis.org/races/greater-st-louis-marathon

Completing this marathon (or half-marathon, 10k, or 5k) is a rite of passage for area runners. Downtown St. Louis transforms into a giant racecourse, looping past the city’s iconic landmarks and ending with a massive street party featuring local food and drinks. Groups can sign up for the National Running Club Championships & Rally and compete to win awards and bragging rights.

 

Ozark Mountain Challenge
Date: May 3
Location: Patterson, Mo.
Registration: ultrasignup.com/register.aspx?did=116161

If you hike nine times up Mudlick Mountain in Sam A. Baker State Park in 12 hours for a total of 17 miles, what do you get? You get the elevation of Mount Olympus in Washington State (7,980 feet) and the satisfaction of joining a special tribe of endurance athletes. Registration for this non-race event includes three meals, aid stations, an after-party, and swag.

 

Tour of Hermann Gravel Challenge
Date: May 3-4
Location: Hermann, Mo.
Registration: offroadracingleague.com/tour-of-hermann-gravel-challenge

Think of it as a choose-your-own adventure gravel bike ride: Participants can pedal as little as one or as many as five loops on the roads surrounding scenic (and hilly) Hermann. But only those who finish all the routes in the allotted time earn entry into the Tour of Hermann Gravel Challenge Elite Club, having conquered 11,700 feet of climbing over 200+ miles.

Berryman 50 Mile & Marathon Trail Races
Date: May 17
Location: Potosi, Mo.
Registration: stlouisultrarunnersgroup.com/berryman-trail-races

Celebrating 25 years in 2025, these races follow the rugged Berryman Trail, nestled in Mark Twain National Forest and named a National Recreation Trail in 1980. The course is entirely forested and highly technical, with a total elevation gain of approximately 2,500 feet per loop. Register by May 1 to receive a 25th Annual Berryman Trail Runs bucket hat.

 

Pedaler’s Jamboree
Date: May 24-25
Location: Columbia to Boonville, Mo.
Registration: pedalersjamboree.com/tickets25

“PedJam” evokes a music festival vibe, but unlike a normal music festival where you walk from stage to stage, you ride your bike from stage to stage with 2,000+ other ticket holders. The ride takes place on the Katy Trail from Columbia to Boonville and back — 30 miles each way — with live bands, food trucks, camping, and beer tents galore on both days.

Macklind Mile
Date: June 28
Location: St. Louis, Mo.
Registration: macklindmile.com/registration

Maybe distance isn’t your thing, but you love a good sprint. This run is only one mile, downhill, making it perfect for anyone — pros, kids, recreationalists, dogs, para athletes, parents with strollers…. All are invited to compete in the festive community event and stick around for music, food, and family-friendly activities throughout the morning.

 

St. Louis Triathlon
Date: June 29
Location: Maryland Heights, Mo.
Registration: runsignup.com/Race/MO/SaintLouis/StLouisTriathlon

Held in and around Creve Coeur Lake Memorial Park, St. Louis’ namesake tri is fast and flat, ideal for both serious racers hoping to shave seconds off their time and also for those just starting their multi-sport journey. A new sprint aquathon (swim/run) joins sprint and Olympic triathlons, paratriathlons, duathlons (run/bike/run), aquabikes (swim/bike), and relays this year.

 

Missouri River 340 (MR340)
Date: July 7-11
Location: Kansas City to St. Charles, Mo.
Registration: mr340.org/register

The world’s longest nonstop river race takes place right here in the Show-Me State. Paddlers in single and multi-person canoes, kayaks, and other watercraft cover 340 miles on the Missouri River over five days, battling the elements as well as their own physical and mental limitations. In short: This is no beer-soaked float trip. You have been warned.

 

Moonlight Ramble
Date: August 9
Location: St. Louis, Mo.
Registration: moonlightramble.com/registration

You haven’t fully experienced downtown St. Louis until you’ve ridden its closed streets at night with thousands of other cyclists rocking multi-colored bike lights and headlamps. The longest-running event of its kind in the U.S., Moonlight Ramble is a parade of illuminated two-wheelers, costumed pedalers, music, and art that needs to be on your bucket list.

Gateway Cup
Date: August 30-September 1
Location: St. Louis, Mo.
Registration: gatewaycup.com/register

The Gateway Cup features four days of competitive cycling that include amateur races, kids’ races, and special events that build up to the men’s and women’s professional races. Each venue (it switches daily) showcases short laps for awesome spectating, commentators announcing the races, food and drink vendors, and a raucous Grand Prix-like atmosphere.

 

MammothMarch Missouri
Date: September 7
Location: Defiance, Mo.
Registration: raceroster.com/events/2025/95344/mammothmarch-missouri

Spend a full day hiking and finish 20 miles in 8 hours. Sounds like a piece of cake? You decide at this event using undulating Lewis and Clark Trail and part of the Katy Trail. The single-circuit loop starts and ends at Defiance Ridge Vineyards, with each finisher earning a medal, personalized certificate, and entry onto MammothMarch’s Wall of Fame.

 

Paddle MO
Date: September 13-17
Location: Brunswick to Jefferson City, Mo.
Registration: paddlemo.org/register

Experience the wild beauty of the Missouri River on a five-day, 100-mile guided excursion. Paddle MO is not a race; it’s an educational and recreational journey that stops at historic towns and includes visits with river experts, immersion in nature, and nightly camping in picturesque surroundings. Bring your boat, they take care of the rest.

 

Pedal the Cause
Date: September 21-22
Location: St. Charles, Mo.
Registration: pedalthecause.org

This is a festive and inclusive cycling event benefiting a truly ambitious cause — nothing short of curing cancer. One hundred percent of the funds raised during ride weekend, which features seven new courses (six road, one gravel), a Spin Zone, a virtual option, a Kids Challenge, Taste the Cause, and more, support breakthrough cancer research in St. Louis.

 

Devil’s Toll Race
Date: October 4
Location: Middle Brook, Mo.
Registration: ultrasignup.com/register.aspx?did=121622

Experience a highlight reel of Ozark Trail sites on this challenging run/hike: Taum Sauk Mountain (the highest point in Missouri), Mina Sauk Falls (the tallest waterfall in Missouri), the Devil’s Tollgate rock formation, the Scour of Taum Sauk Reservoir, and Johnson’s Shut-Ins State Park. Basic navigational skills and ability to traverse steep topography are encouraged.

 

Ride the Rivers Century
Date: October 4
Location: St. Charles, Mo.
Registration: trailnet.org/rides

One of the more unique 100-mile cycling events in the Midwest, Ride the Rivers takes participants on river ferries, urban and rural roads, and recreational trails past orchards, prairies, small towns, and larger cityscapes. At the end of their journey, riders arrive back at a block party on the Streets of St. Charles, featuring food, drinks, and a well-earned rest.

MO’ Cowbell Marathon
Date: October 5
Location: St. Charles, Mo.
Registration: mocowbellmarathon.com/registration

With a course that’s flat, fast, and Boston-qualifying, MO’ Cowbell makes the perfect choice for anyone from first-timer to elite runner. You can expect music, beer, VIP options, spot-on timing, and thousands of jangly cowbells. Choose from marathon, half-marathon, half-marathon relay, 10k, or 5k distance options.

 

Southern Illinois Fat Tire Fest
Date: October 17-19
Location: Ozark, Ill.
Registration: ftf.bike/field-guide

Like a sleepaway camp for bike junkies, this festival is loaded with fun activities. There are multiple daily rides (gravel and trail, beginner to advanced), plus low-key races and contests, a scavenger hunt, and lots of general messing around. And Fat Tire wouldn’t be Fat Tire without great food, cold drinks, treehouse accommodations, and amazing prizes — over $10,000 worth.

 

The Skippo Trail Races
Date: November 1-2
Location: Ballwin, Mo.
Registration: bigrivertrailseries.com/the-skippo

Big River Running hosts two weekends of winter racing at Castlewood State Park in Ballwin each year. The Skippo in November (the other is Castlewood Cup in January) consists of two days of racing at 10k, half-marathon, and 30k distances and includes soaring woods-and-water views, creek crossings, train tressels, and a 200-step wood staircase. Going up!

 

Saint Louis Half Marathon
Date: November 9
Location: St. Louis, Mo.
Registration: stlouistrackclub.com/half-marathon-and-5k

The oldest half-marathon in St. Louis is back, with this year’s runners presented with an all-new course! The paved route starts and finishes at the Muny Festival Grounds in Forest Park and loops around the gorgeous Central Fields, Steinberg/Murphy Lake zone, and Highlands Golf & Tennis Center. Don’t miss this St. Louis Track Club tradition.

Gateway Outdoor Expo + Summit
Date: November 15-16
Location: St. Charles, Mo.
Registration: gatewayoutdoorexpo.com

Browse over 150 booths from retailers and organizations, and try your hand at interactive activities and demonstrations, at the region’s largest outdoor lifestyle and adventure sports show. This year, the expo returns to St. Charles Convention Center and adds two days of presentations and workshops from national and regional outdoor experts.

 

Castlewood 8-Hour Adventure Race
Date: December 6
Location: West St. Louis County, Mo.
Registration: offroadracingleague.com/castlewood-8-hour-adventure-race

This seminal end-of-season event has grown to become the third-largest adventure race in the country. And even though it’s named after Castlewood State Park, don’t necessarily expect it to go through the park on race day. That’s part of the appeal of adventure racing: charging into the unknown with just your gear, skills, and wits to navigate you to the finish.

Author: Brad Kovach is the publisher of Terrain.

Top image: Richard Jefferson.