It may still feel like summer outside, but cooler running weather is right around the corner. With fall approaching, there are plenty of exciting runs and major races to choose from in the Annapolis area, whether you’re getting ready for your first race or adding another medal to your collection.
Annapolis RUN for the Lighthouse
Taking place Sunday, Sept. 20, at Quiet Waters Park, this event offers a half marathon, 5K and 1.25-mile walk. Now in its 17th year, all proceeds benefit The Light House of Annapolis, which works to help individuals and families overcome homelessness and achieve stability.
The half marathon begins at 8 a.m. and must be completed within three hours. The 5K begins at 8:45 a.m., followed by the walk at 9 a.m. All participants must finish by 11 a.m. The half marathon costs $115.48 through Sept. 1 and $129.26 after, while the 5K costs $54 through Sept. 1 and $64.60 after. The 1.25-mile walk is $27.50.
Looking to help the cause even more? This year, the race is accepting donations of new adult sneakers and gently used tennis shoes to support The Light House. Boxed and canned food donations will also be accepted.
Heat It to Beat It
A little farther from Annapolis, Heat It to Beat It takes place Sept. 27 at Under Armour Stadium in Baltimore. Since its founding in 2009, the event has raised more than $3 million to support medical research.
Now in its 17th year, the patient-led event aims to raise awareness of HIPEC, a treatment used for certain cancers in the abdominal cavity. This year’s fundraising goal is $250,000.
Adult registration costs $54.98, while youth registration is $17.61. All participants receive a Heat It to Beat It T-shirt and a free Kona Ice ticket. The program begins at 9:30 a.m. and will also feature a DJ, face painter, coffee truck, Kona Ice and silent auction.
PRO-Vision Memorial Run
This run/walk event offers both a 5K and 10K on Oct. 10 in Severna Park. Taking place along the B&A Trail, the race begins at 8:30 a.m. at the Severna Park Community Center.
Proceeds benefit Athletes Serving Athletes and Chrysalis House, two organizations dedicated to empowering individuals, strengthening communities and creating opportunities for people facing challenges.
Founded in 2023, the race honors Paul Robert Overton, a leader in the Severna Park community. Those interested can sign up here. Registration costs $75.20 for the 10K and $59.30 for the 5K.
Baltimore Running Festival
Back for its 26th year, the Baltimore Running Festival is one of Maryland’s best-known racing events. Supported by sponsors including CareFirst, Under Armour, MedStar and Royal Farms, the multi-distance event takes place Saturday, Oct. 17.
With distances ranging from a full marathon to a 5K, runners will make their way through Baltimore, including the Inner Harbor and Light Street. Half and full marathoners will also pass Patterson Park, while full marathon runners will tackle the dreaded “Heartbreak Hill” around miles 17 to 19.
The full marathon is also a Boston Marathon qualifier, with qualifying times automatically submitted for consideration. There’s still time to sign up, with virtual race prices ranging from $45 to $110 and in-person race prices ranging from $70 to $150.
Bay Bridge Run
Another local classic and fan favorite, the Bay Bridge Run takes participants to new heights — up to 186 feet above the Chesapeake Bay.
The 10K is open to runners and walkers, with 4.35 of its 6.2 miles taking participants across the eastbound span of the Chesapeake Bay Bridge. Participants must be able to maintain a 19-minute-per-mile pace, and walkers are asked to stay in the right-hand lane of the bridge.
There will be eight start waves, A through H, on Sunday, Nov. 8, beginning every 15 minutes from 7 to 8:45 a.m. Waves A and B are reserved for runners, while the remaining waves are open to walkers.
There is no parking at the race site, but parking will be available at Navy-Marine Corps Memorial Stadium, Anne Arundel Community College, the Anne Arundel County Fairgrounds and Annapolis Exchange. Eastern Shore parking options include Chesapeake College and Kent Narrows. Parking costs $20 at each location and includes complimentary shuttle service. Navy-Marine Corps Memorial Stadium parking is limited to 1,000 spots.
Tickets are on sale for $105 through Oct. 31, increasing to $115 in November.
RTB Fair Winds 5K/Fun Run
Now in its fourth year, the RTB Fair Winds 5K/Fun Run takes participants through the meadows and woods of Quiet Waters Park on a fully paved course.
Proceeds support academic scholarships for college students enrolled in science programs as well as camp scholarships for children coping with traumatic loss.
The race takes place Oct. 24 and begins at 10 a.m. Registration is open through Oct. 23. The entry fee is $35 through Sept. 30 and increases to $45 beginning Oct. 1. Select parking lots inside the park will be available on race day.
And because this isn’t just about the running, participants can also compete for best individual costume and best team or family costume.
Stocking Stuffer 8-Hour Endurance Run
Running junkies, this one’s for you! Let’s be clear: This is not your average race.
Taking place Dec. 6 at Terrapin Nature Park in Stevensville, runners have eight hours — from 8 a.m. to 4 p.m. — to complete as many 2.8-mile laps as they can, or want to.
For every completed lap, runners receive a surprise to add to a stocking provided by the race. It’s simple: The more laps you complete, the fuller your stocking gets. Participants take home everything they collect, along with a special “check-out” gift when they finish or the eight-hour clock runs out.
Special prizes will be awarded to the top male and female participants who complete the most laps. Registration is capped at 100 entrants and costs $59.30.
Naptown Half Marathon
Looking for a reason to get outside in December? The Naptown Half Marathon takes place Saturday, Dec. 19, and offers a half marathon, 10K and 5K.
The 5K course was completely revamped last year, allowing participants to start from the same location as the other races. The 5K begins at 7:40 a.m., shortly after the other distances begin at 7:30 a.m.
Starting at Navy-Marine Corps Memorial Stadium on Taylor Avenue, the courses take runners through downtown Annapolis. Half marathoners will cross a bridge before heading out and back along a portion of the B&A Trail.
Participants can register through race day. The half marathon costs $96.90, the 10K is $59.80 and the 5K is $43.90. It’s a great excuse to get outside with friends or family during a time of year when staying warm indoors can be tempting.
Additional Races to Check Out
Looking for even more ways to hit the pavement this fall? The Annapolis Striders have three races remaining in their 2026 Championship Series:
Metric Marathon: On Sunday, Oct. 4, runners can take on a 26.2K — about 16.3 miles — beginning at Southern High School in Harwood. The race starts at 8 a.m. and gives runners looking for more than a half marathon, but less than a full marathon, a unique distance to tackle.
Downs Park 5 Miler: Head to Downs Park in Pasadena on Saturday, Nov. 7, for this five-mile race. The run begins at 8:30 a.m. and is another local option for runners who want to enjoy some cooler fall weather without committing to a longer distance.
Anniversary Run 15K: The Striders close out their Championship Series on Sunday, Dec. 13, with the Anniversary Run 15K at Quiet Waters Park in Annapolis. The race begins at 10 a.m., making it another chance to enjoy one of Annapolis’ favorite running spots before winter officially arrives.
Learn more about the Annapolis Striders Championship Series and individual races on the organization’s website.
Keep your eyes peeled — we’ll be back with Turkey Trot options for the whole family!
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. Charm City Run is also offering several local training groups this fall, including programs geared toward half marathons, the Bay Bridge Run and Turkey Trots. Whether you’re aiming for your first 5K, building toward a longer distance, or simply looking for some extra motivation, joining a local running community can make training more fun and help you stay on track.
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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