Hit the Ground Running: When, Where and How to Race this Fall
As the fall weather kicks in, outdoor time becomes much more enticing. Whether you’re lacing up for your very first race or adding another medal to your collection, there are plenty of fun runs and big races to choose from this season.
You’ll see some races on the list are part of the Championship Series with Annapolis Striders. The local running club participates in eight races each year, and while anyone can sign up, members earn points in their age group across the series for year-end rankings and awards.
October 5
Part of the Championship Series, the Metric Marathon takes runners on a scenic 26.2-kilometer (16.28-mile) route through Southern Anne Arundel County. The race starts at Southern High School in Harwood, offering a challenging but approachable distance. Registration is $15, with a discounted $10 entry for Striders members.
October 18
This marks the 25th anniversary of this Maryland classic that kicks off downtown, at McKeldin Plaza, and takes runners around the Inner Harbor and other sights of Charm City. This race has it all, from the full 26.2 marathon to the classic 5k. The main marathon is a Boston Marathon qualifying event, with the half, 10k and 5k all being less competitive options. Spots are still on sale, with prices set that vary from $70 to $160, and can be found on their website.
Hosted by the Paulstrong team, this fundraiser benefits Orphan Grain Train, a nonprofit providing aid locally and globally. The race offers a 10K run and a family-friendly walk on the scenic B&A Trail. Start and finish at the Severna Park Community Center, where post-race festivities will round out the morning.
October 19
Key School 5k/10k & Family Fun Run
Flat, fast, and community-focused, the Key School’s fall race winds through the Hillsmere Shores neighborhood with views of the South River. Options include a 5K, 10K, and a free mile-long Family Fun Run, making it ideal for runners of all levels. Registration is $30–$35 online, with day-of options available. Can’t make it? Supporters can still snag a race shirt through the $15 “Snooze-In” entry.
October 25
Get ready for a spooktacular morning at Festival Park in Aberdeen, where ghosts, ghouls, and runners unite for the Cats & Bats Haunted 5K. This flat, fast, and family-friendly race has been a pre-Halloween favorite for ten years. All participants receive a custom medal, race shirt, and chip timing, with live and virtual options available. Not up for the full distance? Sign up for the one-mile fun run or simply come for the festive atmosphere. Proceeds support the National PTSD Foundation, making this event more than just frightful fun—it’s meaningful too. Costumes are encouraged, so don’t be surprised if you find yourself racing alongside a bat, a cat, or even a friendly witch! Ticket prices vary and can be purchased online.
Ready, Set, SNIFF! 5K at BARCStoberfest
Celebrate the 21st annual BARCStoberfest with this pet-friendly 5K run/walk and brand-new Half-Mile Pet Parade. The festival atmosphere includes live music, shopping, games, and a dog-friendly beer garden. Registration is $54 and includes a shirt, dog bandana, and drink ticket. Costumes (for people and pets!) are encouraged, and all proceeds benefit the homeless animals cared for by BARCS.
The Richard T. Brennan Fair Winds Memorial Foundation (RTB Fair Winds) was established in 2021 to support higher education, help grieving children who have experienced a traumatic loss, and foster future leaders, visionaries, and problem-solvers in remembrance of RDML Richard T. Brennan’s spirit of inquiry and passionate leadership. In its third year, this race takes place at the beautiful Quiet Waters Park in Annapolis, October 25, all on fully paved trails. Proceeds from the race will go toward supporting academic scholarships for high school graduates, college students majoring in science, and camp scholarships for kids dealing with catastrophic loss. Tickets can be purchased online for $38.10.
October 26
Hosted by Charm City Run and presented by Altra, this Sunday funday race kicks off at 8 a.m. on October 26 from the Charm City Run location in Columbia. Runners, friends and family can enjoy a fantastic post-race celebration at Black Flag Brewing Co., alongside amazing merchandise to celebrate the fall tradition! Looking to run for a cause? Bridges to Housing Stability will receive a share of the race’s revenues! Registration is still available for a one-time fee of $60.30 but will increase after October 12.
November 1
Part of the Annapolis Striders Championship Series, this scenic 5-mile loop course winds through John H. Downs Memorial Park with views of the Chesapeake Bay. The race starts and finishes at the Fernwood Pavilion, with water available at the halfway point. Registration is $25 on race day, with a discount for Striders members. Runners must maintain a 15-minute-per-mile pace, and awards are presented to top finishers.
November 8
Rosaryville Veterans Day Trail Race
Now in its 16th year, this trail classic features 50K and 20K distances on the wooded singletrack of Rosaryville State Park. Expect rolling hills, well-marked trails, and plenty of autumn leaves along the way. With limited entries and generous cutoff times (8 hours for the 50K, 7 for the 20K), this is a welcoming race for both seasoned ultrarunners and trail newcomers. Afterward, enjoy food, music, and fire pits at the post-race celebration. Registration is available on Ultrasignup.
November 9
On November 9, runners and walkers alike get their once-a-year chance to cross the Bay Bridge on foot. Brought to you by Corrigan Sports, the race will see a wave start, with groups leaving between 7 and 9 a.m., taking off in 15 minute intervals. The price for those who register before November 3 is $100, with a $10 increase from November 4 until race day. There is no general parking available at the start or finish, but participants can reserve parking for an additional $20. For more information on fees and additional packages, head to their webpage to learn more.
We’ll update this guide as we hear about more fall races. Be sure to also check back for our upcoming features on turkey trots and holiday runs.
Running Groups and Race Day Preparation
Looking for more than just race day? Local running clubs like the Annapolis Striders and Charm City Run offer year-round opportunities to connect with other runners in Annapolis. Both organizations are also hosting local training groups this fall, making it easier to stay motivated, build mileage safely, and make new friends along the way. Whether you’re aiming for your first 5K or a marathon PR, joining a club is a great way to stay on track and enjoy the season.
A little planning can go a long way when prepping for race day. Start your preparations the night before by laying out your clothes (including your race bibs if applicable), packing necessary items like drinks, food, sunscreen, wipes, and an extra change of clothes (make sure to check the weather). By arriving early, you can also secure a good parking spot and give plenty of time for adults and children to get settled in without feeling hurried. Remember to pack items like energy gels, blister protection, and a portable phone charger if you’re running longer distances.
Know the path so you can choose rest areas or cheering areas, and set up a family gathering place in case anyone gets separated. Above all, maintain your flexibility—it’s acceptable for some races to go better than others. The objective is to establish customs and experiences that transform racing into a family outing, whether you’re crossing the finish line together or watching from the sidelines. The most important tip of all: make sure to have fun racing!
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