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24 Must-Do September/October Races Across The U.S.

Drink wine, learn about Civil War history, get muddy or raise money for cancer research by running one of these fall races.

Drink wine, learn about Civil War history, get muddy or raise money for cancer research by running one of these fall races. 


Annapolis Run for the Light House
Sept. 28; Annapolis, Md. 

This 13.1-miler aims to raise awareness for the hundreds of homeless people in and around the Annapolis area. Benefitting the Light House, a homeless shelter, all proceeds for the half marathon and the ensuing 5K fun run will go directly toward programs such as job counseling and life skills training. An added bonus: The scenic and flat course—taking you through Quiet Waters Park, overlooking the Chesapeake Bay— is as tranquil as they come.


Freedom’s Run
Oct. 4; Harpers Ferry, W.Va.

Get a hearty dose of history by running this point-to-point marathon set in the shadows of the Blue Ridge Mountains near the confluence of the Potomac and the Shenandoah rivers. In 26.2 miles, you’ll run through four national parks, tracing a similar route taken by Confederate soldiers during the Civil War. Channel the spirit of those soldiers as you run along the flat C&O Canal and through rolling battlefields en route to freedom, er, the finish line. Rather run a shorter distance? Choose from a half marathon, 10K or 5K.

Halloween Hustle 5K
Oct. 24; Montgomery Village, Md.

Do the hustle! This 5K isn’t just any old fun run. Participants are encouraged to dress up in their Halloween finest for this out-and-back race. Aside from overall and age-group awards, there will be prizes for best adult, kids and group costumes. A 1K kids race, trick-or-treat activity and a bounce house makes this race a spook-tacular family affair.


Chicago Half Marathon
Sept. 7; Chicago

One of the most popular half marathons in the Midwest, the Chicago Half Marathon and Hope on Wheels 5K will once again bring runners to the historic Jackson Park neighborhood, just south of the Museum of Science and Industry and the site of the 1893 World Columbian Exposition. The course includes a trip through Hyde Park, the University of Chicago campus and south Lake Shore Drive, which features picturesque views of the Chicago skyline. All runners receive a gender-specific tech T-shirt, and the course features at least 15 entertainment groups along the route.



St. Michael’s Old Town Oktoberfest 5K
Sept. 18; Chicago

The summer is filled with weeknight races that are as much a celebration of the season as an after-work exercise. But come Labor Day, they tend to disappear. So take advantage of one of the last of the year with St. Michael’s Old Town Oktoberfest 5K run and walk on Thursday, Sept. 18. Break out the lederhosen or simply enjoy the race in Lincoln Park and get your commemorative beer mug, which you can fill with Sam Adams at the post-race party at Rocco Ranalli’s. Prizes will be awarded for the best costumes, and all runners receive a T-shirt and a $10 voucher for Fleet Feet Sports.

Brookfield Zoo Run Run 5K
Sept. 21; Brookfield, Ill.

This 5K run and walk takes place entirely on the 216-acre property of the Brookfield Zoo and benefits the Chicago Zoological Society Animal Care and Conservation Fund. Runners will get to explore the zoo as the course winds its way past many of the major exhibits. Family and friends are welcome at the zoo to cheer on runners at no additional charge. Those who raise additional funds are eligible to receive additional incentives, such as zoo merchandise and experiences.


Elk Creek Trail Race
Sept. 13; Pine, Colo.

Now you can experience Staunton State Park’s gorgeous trails in race mode during this challenging, community-crafted trail half marathon. You’ll climb 3,800 feet in a single 13.1-mile loop in Colorado’s newest state park, but don’t sweat it. Mount Evans’ views are a worthy reward—if you have time to stop. A limited field means no crowds, and the low-key atmosphere means you can sign up as late as on your way into the parking lot. For uber-athletes, a double-loop full marathon is also an option.

Running of the Bulls Run/Walk
Sept. 20; Estes Park, Colo.

Step back Pamplona, Spain, northern Colorado’s got an event of the same name, only in a different vein—it’s rut season. “There’s a good chance that runners will be cheered on by the bugles of elk,” says race organizer Kristi Ehle. The 3.75-mile high-altitude run/walk laps Estes Lake with views of snow-capped peaks and fall foliage in its prime. After being cancelled by last year’s 1,000-year flood, the event, benefiting Partners Mentoring Youth, is back stronger than ever—and ready to celebrate. Post-race perks are almost as fun as the stampede: Autumn Gold Fest in downtown and a free craft beer from Estes Park Brewery.

Mine to Mine Challenge
Oct. 4, Cripple Creek, Colo.

Now in its third year, this 9K mountain-style road race takes runners from the historic Mollie Kathleen Mine, through an eclectic downtown, ending at the Cripple Creek and Victor Gold Mining Company. With a mix of flats and hills, plus stunning mountain scenery, this growing gem-of-an-event attracts world-renowned athletes and weekend warriors alike. The theme is mined to the end when age-group winners pocket awards made from sample ore, and the top three male and female overall winners win real gold nuggets. Celebrate your hard-earned riches at the after-party, featuring a beer garden and live bands outside The Brass Ass Casino.


Henry Isola Cross Country (4M)
Sept. 14; New York City

Early fall is a time for crisp air and beautiful foliage, but it’s also the time for cross-country races. At this annual event, the New York Road Runners’ first cross-country race of the season, runners take to the turf in scenic Van Cortland Park, a 1,100-acre conservancy located in the Bronx. This race is full of exciting and challenging terrain with Cemetery Hill, the course’s toughest precipice, waiting for runners near the end.

Rock ‘n’ Roll Philadelphia Half Marathon
Sept. 21; Philadelphia

Channel your inner Rocky by tackling this fast and fun event held in the famous City of Brotherly Love. The race starts not far away from the “Rocky Steps” at the Philadelphia Museum of Art and takes runners along both sides of the Schuylkill River. The course is flat and the weather is usually perfect. Consider this one if you are looking for a PR or a great marathon tuneup.

Front Porches Half Marathon
Oct. 4; Bellows Falls, Vt.

If you’re a fan of viewing the beauty of fall foliage, then this race is for you. This inaugural race kicks off in historic Bellows Falls and takes runners along the banks of the Connecticut River. True to its name, the race showcases the village’s beautiful front porches. Race proceeds benefit local drug
prevention efforts.


Team Hope Walk & Inaugural 5K
Sept. 13; Seattle

Huntington’s disease is a devastating genetic disorder that causes nerves in the brain to degenerate, ultimately resulting in the inability to think, as well as move voluntarily. As of right now, there isn’t a cure for the disease, and treatments are minimal. Fortunately, however, many scientists believe that they are close to finding effective treatments for the disease, which means every little donation counts, and events like the Team Hope Walk & Inaugural 5K in Seattle can go a long way. So get out and enjoy the fresh air on Sept. 13 and help the Huntington’s Disease Society of America make a difference for the families affected by this terrible disease.


Kiss Me Dirty Race series
Sept. 20; Portland

Designed to get women “off the couch, out of the house and having fun together,” this women’s event boasts the ever-popular mud, obstacles and non-competitive atmosphere only a fun run can bring. Don’t worry, dudes—you’re invited to participate as well, as long as you don your favorite “drag” attire and enter in the drag wave. Race proceeds benefit gynecological cancer research—and if that’s not enough to get you dirty, check out the names of the obstacles on the website!

The Biggest Loser RunWalk Race Series Half Marathon & 5K
Oct. 12; Seattle

Dan and Jackie Evans lost a combined total of 225 pounds on season 5 of the popular reality show “The Biggest Loser,” and they have kept the weight off through running and healthy eating. Now, they are the official spokespeople of The Biggest Loser RunWalk race series, which seeks to help people get fit by providing participants with a non-intimidating race environment. The race also features a kids 1-mile fun run. And the best part is if you like how “The Biggest Loser” puts on a race, you have multiple events from around the country to choose from, including off-road challenges and events at Six Flags theme parks.


Buffalo Stampede 10-Mile Run/Walk
Sept. 7; Sacramento, Calif.

This year’s race is the 40th running of the Sacramento tradition, which has long been a kickoff to the fall racing season. The race is one of four annual events put on by the Buffalo Chips Running Club, known for being Sacramento’s biggest and most welcoming running group. (It even has a walkers group and a kids program.) Part of the Buzz Oates Run Sac Race Series, the Buffalo Stampede is a points-based competition that offers runners a chance to win portions of the $6,000 prize purse. According to the official rules, the prize is divided by age-graded performances in more than a dozen top Sacramento-area road races.


Sept. 21; San Diego

Pancreatic cancer is one of the deadliest cancers in the U.S. with only a 6 percent five-year survival rate, and yet it is also historically underfunded. So get out on the streets of San Diego—you’ll have some fun in the sun at Mission Bay Park and do your part for a good cause in the process. The race hopes to raise $216,000 for pancreatic cancer research, and offers runners the ability to donate to specific teams who are running and raising money in honor of those who are suffering from or have lost their lives to the terrible disease.

Rock ‘n’ Roll San Jose Half Marathon & 10K
Oct. 5; San Jose, Calif.

This city’s Rock ‘n’ Roll event is becoming more popular every year. Last year the race had a record-breaking 17,000 runners participate. In addition to being able to run on a scenic course dotted with live, local bands and cheer squads, participants receive a finisher’s medal, gear bag and free admission into the post-race festival and two-day health and fitness expo. Still need convincing? Runners who participate in two or more Rock ‘n’ Roll Marathon Series events from January through December can earn various “heavy medals” such as the Rock Encore medal for completing two races, or the Rock Star medal for completing five.


Head for the Cure 5K
Sept. 13; Houston

With around 200,000 people diagnosed with brain cancer annually in the U.S. alone, Head for the Cure is working to find a cure one step at a time. If you want to run for a reason, this 5K is your race. Not only does it raise thousands of dollars for the Head for the Cure organization, but it also serves as an important tribute to those fighting brain cancer and those who have lost their battles. Whether you have a personal connection to the cause or are simply looking to make a difference, round up a group of friends and get training. With a 5K walk and run, as well as a kids fun run, there’s something for everyone at this event.


Sept. 14; San Antonio

As part of the 2014 Gusto Race Series, the September event includes 5K, 10K and 15K options. If you’re really looking for some motivation, the series runs in conjunction with the Carrerathon half marathon and marathon training programs, offering training runs and races leading up to your goal event. The Gusto Run starts at San Antonio’s Martin Luther King Park, where participants run along the Salado Creek trails with plenty of scenic greenways. Professionally marked, this event also offers water and electrolytes on the course, as well as much-deserved cold beer and food at the finish line. The run benefits the nonprofit Habitat for Humanity, so you’ll be doing something good for both yourself and others by running this race.

Half Marathon and Vintage 5K
Oct. 5; Lubbock, Texas

Part of the Texas Wine Series, this half marathon and 5K are held on the grounds of the Llano Estacado Winery. The perks of a race hosted on a winery not only include experiencing the beautiful landscapes of Texas wine country, but also having the chance to enjoy a totally unique Food and Wine After Party. Complete with libations featuring the locally harvested grapes and a mouthwatering array of food and appetizers, this event rewards finishers like no other race does. What’s more, in addition to winery fare, all runners receive a technical T-shirt, finisher medal, wine glass, custom runner’s sack and personalized bib number.


Endless Summer 10K Cross Country & 5K Beach Run/Walk
Sept. 13; St. Augustine, Fla.

Choose between a 10K cross-country run over soft sand, uneven terrain and mixed pavement types or a casual 5K run-walk on a low-tide beach. This 11th annual event put on by Don’s Friends and the Friends of Anastasia benefits more than 1,600 acres and 4 miles of pristine beach within Anastasia State Park. Take a tour of the varied landscape during the 10K, which begins and ends on the beach and travels through the hammocks and salt marsh, providing a challenging course amid Florida’s heat and humidity. Race fees include entrance to the park for the day, so pack a picnic and plan for an afternoon of beachside lounging.


Hot Lips Hustle 5K
Sept. 20; Marietta, Ga.

Don a creative costume or previous “Hot Lips” race shirt and join more than 400 runners at this 10th annual 5K that culminates with a live DJ, lips tattoos and a tasty food spread, complete with an ice cream bar. Kicking off at 8 a.m. at Holy Trinity Church, the community event was founded by a local 12-year-old girl who was born with a cleft lip and wanted to help other children who can’t afford treatment for the birth defect. The chip-timed race benefits Smile Train, a nonprofit that performs surgeries on children worldwide with a cleft lip. To date the organization has raised enough money to fund surgeries for 243 children.

Miami Children’s Hospital 5K Run/Walk
Sept. 20; Miami

Raise funds for the children and families at Miami Children’s Hospital during this fourth annual 5K. The healthcare system’s largest annual community event, the race aims to increase awareness for the hospital’s pediatric sub-specialties and cutting-edge research. Participate with a team or individually and enjoy a course that begins in front of Coral Gables City Hall and travels along the charming neighborhood’s Spanish-inspired streets. The event will also include a kids fun run and kids fun zone. Post-race celebrations take place in Vendor Village, complete with music, awards, food and beverages.